The Players Ball: A Genius, a Con Man, and the Secret History of the Internet’s Rise

Posted on October 4, 2022 by Luke Ford

David Kushner writes in this 2019 book:

Sitting back in his office in Tijuana, Cohen readily spun his story on the phone to anyone who’d listen. “When Kremen filed this lawsuit, he did us a big favor,” Cohen told Luke Ford, who wrote a widely read blog about the online porn business, “because if you don’t sue someone within a period of time, it can be construed as giving implied permission. We decided at that point, instead of fighting forty lawsuits by people using the name Sex.com, to take care of Kremen.” This included both Fantasy Man and Warshavsky, whom Cohen considered part of Kremen’s team. “We’ve got Warshavsky’s tit in a wringer,” he went on. “We’ve got him cold. He’s fucked.”
Cohen slipped into his pedantic mode, deriding the other dot-com moguls as technological neophytes overinflating their claims. “We have 8,799,232 members,” he told Ford. “The other adult internet sites are not even in the ballgame. Most people do not understand the internet. You get these fools like Seth Warshavsky who claims he’s doing all these millions of dollars’ worth of business. If writers were more technical they could check out the information.”
Cohen told Ford to do a WHOIS search for Sex.com, and waited as he heard Ford’s fingers rattle across his keys. He wanted to show Ford proof that he was dominating Warshavsky’s traffic. “Do you see the number 11083?” he asked. “That’s an autonomous system number. That means you report to more than one place. That means that more than one ISP feeds you.” The implication was that Sex.com needed more than one internet service provider to handle all its eyeballs.
He had Ford then type in the address of Warshavsky’s site, Club Love. “Hear that noise in the background?” Cohen asked, as he put the phone up to his own computer, which played back a fuzzy sound like TV static. “Club Love’s internet provider is cable and wireless,” he went on. “He’s running out of an IP address of 166.48.217.250. Club Love is registered as JNS Communications Inc. and the address is 208.139.0.21. He only has one ISP. He’s probably running less than a T3 line, and yet he claims he’s doing all this business. From what I can see he’s not running more than a couple of T1s. His claims of millions of dollars are all BS.
“Now, let’s take a look at Cybererotica. Cybererotica is fed by IGallery. IGallery. Cybererotica is running greater than T3. About 60–70 megs, probably two T3s. It looks like they have a big video stream coming through. Clublove is a dinky site. Cybererotica doesn’t even have an autonomous system number. Bandwidth is not indicative of how much money you make. You can make millions of dollars with TI if you’re running nothing but text. But once you start doing video and pictures, it eats up more bandwidth. For every dollar made, how much is kept? Cybererotica does lots of webhosting and buying of other people’s traffic. He has great gross but shitty net. While Sex.com has tremendous gross and a 98% net, I don’t need to buy traffic. That is what separates the men from the boys.”

Author David Kushner lacks basic reading comprehension. The following actions and comments he attributes to me are clearly attributed on my 1999 blog to a “Vegas Lee”, who is definitely not me.

Curious to learn more, Ford drove down across the border to meet the man once and for all. “I wanted to see this infamous Cohen everyone always talks about,” as he blogged soon after. Once in Tijuana, he came to a busy thoroughfare with a median of palm trees. Strip malls with UPS stores, tanning salons, and dentist offices lined either side of the road. He pulled into one spot along Diego Rivera Avenue, and went into a brand-new office building, where he was greeted by Jim Powell, Cohen’s gray-haired associate of many years. Powell showed Ford around the computer room, which buzzed with servers and wires and heat. It seemed impressive, but, then again, he had no idea who owned what. But the man himself was nowhere to be found, having gone to Vegas, he was told.
Before long, Ford had had enough. He considered the industry leaders his friends, he later wrote, and descending into the belly of a beast, where Cohen and his cronies were suing everyone into oblivion, was making him feel queasy. “These people are into a very heavy revenge trip that goes well beyond scary and it seems to me they do not care about the harm to our industry that they will cause,” he later wrote. “I felt so sick after seeing what I saw that I just made an excuse and left Tijuana.”

I wonder how many other stupid mistakes the author made?

Here is his bio at the back of the book:

David Kushner is an award-winning journalist and author. His books include Masters of Doom: How Two Guys Created an Empire and Transformed Pop Culture; Jonny Magic & the Card Shark Kids: How a Gang of Geeks Beat the Odds and Stormed Las Vegas; Levittown: Two Families, One Tycoon, and the Fight for Civil Rights in America’s Legendary Suburb; Jacked: The Outlaw Story of Grand Theft Auto; and Alligator Candy: A Memoir. Kushner is also author of the graphic novel Rise of the Dungeon Master: Gary Gygax and the Creation of D&D , illustrated by Koren Shadmi; and the ebook, The Bones of Marianna: A Reform School, a Terrible Secret, and a Hundred-Year Fight for Justice. Two collections of his magazine stories are available as audiobooks, The World’s Most Dangerous Geek: And More True Hacking Stories and Prepare to Meet Thy Doom: And More True Gaming Stories.

A contributing editor of Rolling Stone , Kushner has written for publications including The New Yorker, Vanity Fair, Wired, The New York Times Magazine, New York, Esquire , and GQ , and has been an essayist for National Public Radio. His work is featured in several “best of” anthologies: The Best American Crime Reporting, The Columbia Journalism Review’s Best Business Writing, The Best Music Writing, and The Best American Travel Writing.

He is the winner of the New York Press Club award for Best Feature Reporting. His ebook The Bones of Marianna was selected by Amazon as a Best Digital Single of 2013. NPR named his memoir, Alligator Candy, one of the best books of 2016. He has taught as a Ferris Professor of Journalism at Princeton University and an adjunct professor of journalism at New York University.

Here are some highlights from the book:

* Among those who were seeking Cohen out was Yishai Hibari, an Israeli musician turned adult webmaster who wanted to take out ads on the site. Word was that Cohen was doing three times the traffic. Among the porn stars in bikinis and guys with greased-back hair, he saw what he recalled to be “a funny chubby guy with an important look on his face,” walking a small white Chihuahua with a red ribbon around its neck. Cohen was always chatty, and chummy, friends never saw him in a bad mood.

* It didn’t take long for the success to go to Cohen’s head. He became known for wandering porn shows with a smug smile, and a polo shirt embroidered with the Sex.com logo. Even among the rulers of the Wild Porn West online, he soon gained an unseemly reputation. Just as he had done for years, he put his amateur trademark attorney scam to use by suing anyone, and everyone, who had the word sex in a domain name. Serge Birbair, the owner of sexia.com, was among those who, as he put it, was “harassed by Stephen Cohen.” When hit with Cohen’s lawsuit, he didn’t have the money to fight back against the traffic king—and chose instead to relent, and hand over sexia.com to Cohen. “It cost me money to defend myself, and it cost me a lot of grief,” as one pornmaster put it after caving in. “Eventually, I decided it ain’t worth the fight.”
Cohen reveled in the power. No one could stop him with Sex.com on his side—not even the guy who claimed to own it. One day, Cohen received a certified letter from Kremen’s attorney, demanding he not only cease and desist using Sex.com, but send the money he’d earned from the site Kremen’s way. Cohen had one response. Kremen could go fuck himself. He’d been selling sucking and fucking online since the 1980s, and Sex.com was rightfully his. As he later told Kremen’s attorney, “If anybody stole it, it was Gary Kremen stealing it from me.”

* While Kremen busied himself with new investments and consulting work, he hired a young attorney, Sheri Falco, to navigate the uncharted waters of a potential lawsuit. Falco, an intellectual property attorney, found Kremen doing a million things, as usual, in his office—starting an incubator, making calls, surfing the net. It didn’t take long poking around for her to find out that Cohen was on a lawsuit tear of his own, riding on the back of the trademark protection he filed. She hit back, filing a trademark opposition to put his on hold.
Going on the public record against Cohen had another unintended effect. It got the attention of the many enemies he was making in the online porn industry. And, before long, Falco got a call from the two biggest, and most powerful, ones of all, Ron “Fantasy Man” Levi and Seth Warshavsky, who had an urgent message for Kremen. They wanted to help him take Cohen out.
They were good friends to have. Fantasy Man was considered by many to be the godfather of the online porn business. A dark-haired, imposing strongman, he lived in a ten-thousand-square-foot California mansion. Fantasy Man had been hustling since learning to shoot pool from the basis of the movie The Hustler himself, Fast Eddie, when he was just fourteen. With a knack for business and a passion for technology, Fantasy Man made his first fortune in audiotext, or phone sex, and parlayed that into the first large network of adult sites on the internet, Cybererotica.

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Wired: The High Cost of Living Your Life Online

Posted on October 3, 2022 by Luke Ford

From Wired:

Without the ability to find out how their identity is ricocheting around the virtual world, people often feel a fight-or-flight response when they’ve been online for many hours—and even after they’ve logged off.

“It’s kind of an adapted hyper-vigilance. As soon as you send something out into the virtual world, you’re sort of sitting on pins and needles waiting for a response,” Lembke says. “That alone—that kind of expectancy—is a state of hyperarousal. How will people respond to this? When will they respond? What will they say?”

It would be one thing if only you saw any negative reactions, Lembke says, but they’re often available for everyone to see. She says this exacerbates feelings of shame and self-loathing that are already “endemic” in the modern world.

We are social creatures, and our brains evolved to form communities, communicate with each other, and work together.

I think most of this anxiety has to do with whether or not you live in reality, have friends, community and a solid sense of self with the ability to self-validate, and whether or not you have over-arching positive purpose to your life. If you are not contributing, then it would be best to live in the cave.

I have over-arching purpose to what I do online. One purpose is to learn. Another purpose is to laugh. Another purpose is to stay in touch with friends and family. Another purpose is to make money. Another purpose is thinking socially. At age 56, I realize that when I just go off on my own with an intellectual fixation, it’s often divorced from reality. I’m not unique here. We are evolutionarily adapted to being extraordinarily good at seeing through other people’s attempts to manipulate us and we tend to be terrible at evaluating our own thinking (excessive self-confidence is adaptive because it holds the feeling of insignificance at bay). So when an idea grabs me, I want to talk about it, and the more smart people I can talk to, the more wisdom I get. I think better when I think socially. Because I have an ego and I don’t want to get unnecessarily humiliated online, I try to think things through reasonably and responsibly and then I listen carefully to the feedback I receive.

I like to explore dissident ideas that the MSM reflexively dismisses and demeans. This is one way I feel significant. I have a niche and I do it well. I like to discuss the forbidden without being reflexively pro or con. I have no sacred cows (though I do have interests in addition to values and these interests and values shape my choices online and off). My audience seems to be about 80% dissidents and I think they appreciate that I neither loathe them nor snow them. I’m not a pundit nor a syndicated radio host who makes his living telling people what they want to hear. I’m not a populist. I don’t believe that wisdom resides with the people. I’m not an elitist either. I don’t believe wisdom resides with the elite. I don’t believe any group or class is consistently wise. I believe both sides of the political spectrum are normal natural reflections of evolutionary adaptations. In some situations, the conservative approach is more adaptive, and in other situations, a more radical approach is more adaptive.

I think about what I say publicly, and I try to say it in ways that people can hear me without getting unnecessarily hurt. Since I started blogging in 1997, I’ve had a sense that I want to keep at least 51% of my audience on my side.

Wired says: “Constantly posting content on social media can erode your privacy—and sense of self.”

So one needs to use good judgment about what one shares, whether online or off. The more important someone is to me, the more reluctant I am to talk about them publicly or privately. For example, when good friends of mine get gossiped about, I rarely defend them because it doesn’t do any good and I don’t want to reveal too much of myself. If I really like a woman, I rarely talk about her. I have a few intense friendships and I don’t usually discuss them. In Judaism, the more sacred something is, such as a Torah scroll, the more protection it generally enjoys.

People who constantly post online seem to lack a sense of self. There’s an air of desperation about their production. They need other people to tell them who they are. On the other hand, there are great scholars such as Marc B. Shapiro who post many videos online and I don’t see anything dysfunctional there.

Wired says: “TO BE ONLINE is to be constantly exposed.”

It depends upon what you are exposing. If you are exposing the rabbinic response to the rise of Reform Judaism, I don’t see a lot of downsides.

Wired says: “It can sometimes feel like the whole world has its eyes on you.”

Then you are doing it wrong and you need to step away. This problem is but a symptom of a deeper problem.

Wired: “Being observed by so many people appears to have significant psychological effects.”

Exposure is not for everyone whether it is online or off. Some people are better off with a low-key moderately paying job than a high-stress high visibility job.

Wired: “He says people are receiving dozens of notifications every day and that they often feel they can’t escape their online lives.”

I rarely experience this because I have my notifications turned off. I also don’t suffer from the delusion that everyone is checking out what I say online. At the same time, when I speak online, I try to have in mind that anyone I come in contact with may have tuned in to me. I know it is unlikely to be true, but I find it a reasonable and responsible attitude for my online production. I like the idea that everyone knows everything. I find it sobering and it helps me to make better decisions. There’s not much in my life that I’m hiding and so I don’t usually feel great anxiety posting online.

Wired: “Even when you’re not on the screens, the screens are in your head.”

Yes. Even when you’re not playing golf, golf can be in your head. Even when you’re not having sex, sex can be in your head. Even when you’re not looking at porn, porn might be in your head. Even when you’re not at work, work might be in your head. Even when you’re not facing your rabbi, your rabbi’s face might be in your head. We are porous (in the traditional view). We’re not buffered autonomous strategic agents driven by our reason (the liberal view).

Everything we do affects us. The online world is as real as any other part of our life. How you conduct yourself online will feed back into your regular life just as how you conduct yourself at work will affect how you speak online.

I have a dozen 12-step sponsees. Even when I am not directly working with them, I carry a sense of them with me through my day. I ask myself before taking an action, “How would my sponsees feel about this? Would this look like recovery to them? Would members of my community see this as a good thing?” I have an infinite ability to fool myself, but fooling a community is more difficult.

Wired: “One value of privacy is that it gives us space to operate without judgment. When we’re using social media, there are often a lot of strangers viewing our content, liking it, commenting on it, and sharing it with their own communities. Any time we post something online, thus exposing a part of who we are, we don’t fully know how we’re being received in the virtual world. Fallon Goodman, an assistant professor of psychology at George Washington University, says not knowing what kind of impression you’re making online can cause stress and anxiety.”

Yes, we all need privacy. Over-sharing is usually maladaptive. There need to be sacred spaces.

Wired: ““When you post a picture, the only real data you get are people’s likes and comments. That’s not necessarily a true indication of what the world feels about your picture or your post,” Goodman says. “Now you’ve put yourself out there—in a semi-permanent way—and you have limited information about how that was received, so you have limited information about the evaluations people are making about you.””

If you live in reality, you’ll likely have a fairly accurate understanding of how your picture was received.

Wired: “we construct our identities through how we’re seen by others. Much of that identity is now formed on the internet, and that can be difficult to grapple with.”

Yes, so you have to pay attention to shifting social norms. What was acceptable to say one year is unacceptable the next year. Also, you need to pay attention to who you value. The five people closest to us are going to be a fairly accurate reflection of ourselves. If you have five people who love you, the opinions of strangers won’t matter as much.

Wired: “This virtual identity is a composition of all of these online interactions that we have. It is a very vulnerable identity because it exists in cyberspace. In a weird kind of way we don’t have control over it. We’re very exposed.”

We’re very exposed off-line as well as online. The world is a more dangerous place than we think. And we’ve never had the power to control what other people think of us. Our reputations do not belong to us because they reside in the minds of others.

Wired: “Without the ability to find out how their identity is ricocheting around the virtual world, people often feel a fight-or-flight response when they’ve been online for many hours—and even after they’ve logged off.”

The more solid your off-line identity, the less vulnerable you’ll be to the opinions of strangers. If you are furiously building a false identity online to feel important, that’s a symptom of a deeper problem — a lack of self.

Wired: “It’s kind of an adapted hyper-vigilance. As soon as you send something out into the virtual world, you’re sort of sitting on pins and needles waiting for a response. That alone—that kind of expectancy—is a state of hyperarousal. How will people respond to this? When will they respond? What will they say?”

The more solid my off-line life, the less I experience this. On the other hand, sometimes I feel apathetic and the easiest way for me to get aroused is to post something. Knowing the dangers of posting online, I’m incentivized to do this carefully. The danger gives me a burst of adrenaline, a shot of power and agency, and I think I usually do more good than harm with these efforts.

Wired: “We are social creatures, and our brains evolved to form communities, communicate with each other, and work together. We have not evolved to expose ourselves to the judgment of the whole world on a daily basis. These things affect everyone differently, but it’s clear many people regularly feel overwhelmed by this exposure level.”

Sometimes we benefit from more exposure and sometimes we benefit from less. Whatever level of exposure you choose, it will come with a price. There’s no right or wrong answer here. There are only trade-offs.

I’ve been blogging since 1997 and livestreaming since 2015. It seems to me that more than 90% of the people I’ve interviewed for my blog have not regretted it, while most people who’ve come on my livestreams would be better off with less exposure, and only a few guests would benefit from more exposure. On the other hand, I notice people are more likely to get into trouble for what they write rather than for what they say on a stream.

I enjoy swimming in the ocean, but it’s not for everyone. I enjoy public speaking, but it’s not for everyone. Most people would happily go their entire lives without ever giving a speech.

Incidentally, most of the time I am online, I am not posting anything. I am just working, learning and enjoying.

The best book I’ve read on this topic is Virtually You: The Dangerous Powers of the E-Personality by Elias Aboujaoude, a psychiatrist in Silicon Valley.

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Biden Favors Lawyers Over Economists

Posted on October 3, 2022 by Luke Ford

From the Washington Post:

The change captures a shift in the party — also spurred by Trump — as Democrats pay more attention to powerful gestures and less to following the intellectuals and policy savants often perceived as out of touch with political currents. In the Obama administration, Summers helped shoot down some of then-Vice President Biden’s proposals to revive manufacturing for blue collar workers that he viewed as likely to prove ineffective, although the two worked together on the same side of the Detroit auto bailout. But critics say there are significant risks to this newer approach, pointing to soaring inflation — which Summers warned of, only to be ignored — as evidence.

“The economists are in a much more reactive position than they were in the Obama administration,” said one senior Biden administration official, speaking on the condition of anonymity to reflect internal dynamics. “They are being told, ‘Here’s what the policy is.’ There may be some flexibility to change things on the edges, but in general, by the time they weigh in, the policy has already been set.”

This article misses the point that Trump didn’t just make gestures for his audience, he created concrete benefits. Real wages for the least educated rose at the most significant rate in 50 years. In 2020, Trump crushed illegal immigration with his remain in Mexico program.

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Stimulus & Inflation

Posted on October 2, 2022 by Luke Ford

If Donald J. Trump had signed on for a second Covid stimulus package in the summer of 2020, he would have been re-elected. Joe Biden signed on to massive Covid stimulus, won the 2020 election, and set off massive inflation.

Sometimes doing the right thing results in a massive personal loss and sometimes doing the wrong thing results in a massive personal gain.

Successful pundits feed an audience what it wants to hear, even if it is bad for them.

In 2008, Dan Shelley, former news director and assistant program director at Milwaukee’s WTM radio, wrote for Milwaukee Magazine:

…talk show hosts…are popular and powerful because they appeal to a segment of the population that feels disenfranchised and even victimized by the media. These people believe the media are predominantly staffed by and consistently reflect the views of social liberals. This view is by now so long-held and deep-rooted, it has evolved into part of virtually every conservative’s DNA.

To succeed, a talk show host must perpetuate the notion that his or her listeners are victims, and the host is the vehicle by which they can become empowered. The host frames virtually every issue in us-versus-them terms. There has to be a bad guy against whom the host will emphatically defend those loyal listeners.

The enemy can be a politician — either a Democratic officeholder or, in rare cases where no Democrat is convenient to blame, it can be a “RINO” (a “Republican In Name Only,” who is deemed not conservative enough. It can be the cold cruel government bureaucracy. More often than not, however, the enemy is the “mainstream media…”

In the talk radio business, this concept, which must be mastered to be successful, is called “differentiating” yourself from the rest of the media. It is a brilliant marketing tactic that has also helped Fox News Channel thrive. “We report, you decide” and “Fair and Balanced” are more than just savvy slogans. They are code words signaling that only Fox will report the news in a way conservatives see as objective and truthful.
Forget any notion, however, that radio talk shows are supposed to be fair, evenhanded discussions featuring a diversity of opinions. The Fairness Doctrine, which required this, was repealed 20 years ago. So talk shows can be, and are, all about the host’s opinions, analyses and general worldview. Programmers learned long ago that benign conversations led by hosts who present all sides of an issue don’t attract large audiences.

One entire group that rarely gets on the air are the elderly callers – unless they have something extraordinary to say. Sadly, that doesn’t happen often. The theory is that old-sounding callers help produce old-skewing audiences. The target demo is 25 to 54, not 65 and older…
Talk show fans are not stupid. They will detect an obvious phony. The best hosts sincerely believe everything they say. Their passion is real. Their arguments have been carefully crafted in a manner they know will be meaningful to the audience, and that validates the views these folks were already thinking.

A smart talk show host will, from time to time, disagree publicly with a Republican president, the Republican Party, or some conservative doctrine. (President Bush’s disastrous choice of Harriet Miers for the Supreme Court was one such example.) But these disagreements are strategically chosen to prove the host is an independent thinker, without appreciably harming the president or party. This is not to suggest that hosts don’t genuinely disagree with the conservative line at times. They do, more often than you might think. But they usually keep it to themselves.

If you lack compelling arguments in favor of your candidate or point of view, attack the other side. These attacks often rely on two key rhetorical devices, which I call You Know What Would Happen If and The Preemptive Strike.

Using the first strategy, a host will describe something a liberal has said or done that conservatives disagree with, but for which the liberal has not been widely criticized, and then say, “You know what would happen if a conservative had said (or done) that? He (or she) would have been filleted by the ‘liberal media.’ ” This is particularly effective because it’s a two-fer, simultaneously reinforcing the notion that conservatives are victims and that “liberals” are the enemy.

The second strategy, The Preemptive Strike, is used when a host knows that news reflecting poorly on conservative dogma is about to break or become more widespread. When news of the alleged massacre at Haditha first trickled out in the summer of 2006, not even Iraq War chest-thumper Charlie Sykes would defend the U.S. Marines accused of killing innocent civilians in the Iraqi village. So he spent lots of air time criticizing how the “mainstream media” was sure to sensationalize the story in the coming weeks. Charlie would kill the messengers before any message had even been delivered.

Good talk show hosts can get their listeners so lathered up that they truly can change public policy. They can inspire like-minded folks to flood the phone lines and e-mail inboxes of aldermen, county supervisors, legislators and federal lawmakers. They can inspire their followers to vote for candidates the hosts prefer. How? By pounding away on an issue or candidate, hour after hour, day after day. Hosts will extol the virtues of the favored candidate or, more likely, exploit whatever Achilles heel the other candidate might have. Influencing elections is more likely to occur at the local rather than national level, but that still gives talk radio power.

By the way, here’s a way to prognosticate elections just by listening to talk shows: Except in presidential elections, when they will always carry water for the Republican nominee, conservative hosts won’t hurt their credibility by backing candidates they think can’t win. So if they’re uncharacteristically tepid, or even silent, about a particular race, that means the Democrat has a good chance of winning. Nor will hosts spend their credibility on an issue where they know they disagree with listeners.

…This brings us to perhaps the most ironic thing about most talk show hosts. Though they may savage politicians and others they oppose, they fear criticism or critiques of any kind. They can dish it out, but they can’t take it.

…But the key reason talk radio succeeds is because its hosts can exploit the fears and perceived victimization of a large swath of conservative-leaning listeners. And they feel victimized because many liberals and moderates have ignored or trivialized their concerns and have stereotyped these Americans as uncaring curmudgeons.

Because of that, there will always be listeners who believe that [they]are the only members of the media who truly care about them.

Political scientist James Joyner wrote Feb. 21, 2021 about talk radio:

“[Rush] Limbaugh’s schtick ultimately transformed the conservative movement in destructive ways because it showed how lucrative playing to the predudices of an aggrieved base can be… …[A] business model that depends on keeping people riled up and feeding their belief system will inevitably become mean-spirited and dishonest. Discussions of nuanced differences of emphasis—which is where politics in a democracy should naturally gravitate—aren’t enough to get millions to tune in for three hours a day, every day. No, the opposition must be monsters out to destroy all that the Good People hold dear.”

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Greg Giraldo – A Comedian’s Story

Posted on October 1, 2022 by Luke Ford

Here are some excerpts from this 2019 book:

* “Every day there’s a story in the paper about how shitty our schools are,” Greg Giraldo tells the crowd. Although he has performed this bit hundreds of times, his delivery comes off as instinctive and unrehearsed. With his right hand gripping the microphone, he pauses for a beat, and continues.

“I read a book—it was filled with letters that soldiers during the Civil War had written to their girlfriends back home. These guys were kids—they were 14-, 15-year-old kids. Most of these guys had never even been to school. But every single letter in the book was incredible.”

The onlookers go quiet for a moment as Greg alters his voice to mimic an exaggerated 19th-century Southern accent.

“My dearest Hannah. This morn finds me wracked by the fiery pangs of your absence.”

Laughter builds and quickly spreads throughout the Comedy Works audience. Before letting the chuckles subside, Greg continues: “I’ll bear your cherished memory with me as I battle the forces of tyranny and oppression.”

Speaking in his natural, slightly raspy New York tone, Greg says: “Now think about what the typical letter from your average modern-day soldier to his girlfriend back home in like New Jersey’s gotta read like.”

Adopting a New Jersey accent, Greg continues: “Dear Marie. It is hot as fuck out here.”

Applause mixes with laughs, and he resumes: “It is hard to fight these sand monkeys wit’ your balls stuck to your legs. It is very, very hot out here because I am in the dessert.”

Acknowledging the intentional mispronunciation of desert, the fans reward Greg with an extended applause break. Back in character, Greg punctuates the joke: “What else did I want to axe you? Oh yeah, don’t fuck nobody till I get back.”

* Gregory Carlos Giraldo was born on December 10, 1965, in the Queens borough of New York City. He grew up in a close-knit, Roman Catholic home with his two younger siblings—a brother, John, and a sister, Elizabeth—and their parents. Greg’s mother, Dolores, lived in Spain before emigrating to the United States. Alfonso, Greg’s father, was born in Colombia and worked as a fuel-purchasing manager at Pan Am Airlines.

Greg’s parents spoke only Spanish at home, and most of their family friends conversed in it as well. Greg heard English on television and on the playgrounds and streets of Jackson Heights, Queens, but nowhere else until he entered school. The dual linguistic heritage was a boon in practical terms, as Greg became totally at ease in both languages and gained knowledge of two foreign cultures—not to mention the American one that he was born into.

* Greg graduated from Columbia in 1987, and as he put it, felt “dragged along by fate” to enter Harvard Law School. Law school was a default choice rather than a lifelong passion for Greg. Some of his Columbia friends teased him about his academic choice. “How come everyone’s acting like I sold out?” he asked. Downplaying his acceptance, Greg told his friends that Harvard needed another Hispanic. Greg entered Harvard a year before another famous alumnus, Barack Obama, who had allegedly scored five to 10 percentage points lower on the LSAT than Greg had.

* His Ivy League education didn’t focus on vocational preparation. Instead, it emphasized philosophy, rhetoric, and debate—subjects Greg would later put to good use.

* After graduating from Harvard, Greg started working in September 1990 at the same international law firm where he had worked during the previous summer—Skadden, Arps, Slate, Meagher & Flom, one of the most prestigious firms in New York. To many in the legal field, a Skadden pedigree carried more cachet than even a Harvard law degree.

Skadden gained prominence in the 1980s when the firm was at the epicenter of a fervent mergers and acquisitions market. The real estate and Wall Street booms helped Skadden generate record revenues. In 1985, it ranked as one of the country’s top three largest law firms. Skadden lured young attorneys with its prestige and pay. Skadden practically built a pipeline from Harvard Law School. By the time Greg joined the firm, it had a sterling reputation, but money didn’t roll in as fast as it had in the ’80s heyday.

Greg’s summer internships were an unrealistic prelude to the treacherous and cloistered career he had now embarked on. Life at big law firms in the ’90s was a grind, not a job where Greg could phone it in. All-nighters were common. Those who worked more than 100 hours a week were praised by other lawyers in the hallways. Brainpower pervaded. Greg could use his entire vocabulary without appearing pompous.

Power partners, mostly overweight men, catered to executive clients of a similar ilk. Large bottles of Tylenol were displayed on mahogany desks like status symbols of the migraines the work caused. Other stronger and more addictive vices were hidden from sight. The chain of command was almost militaristic.

* However, pro bono projects were included too. Greg teamed up with Klein on one such task. It had nothing to do with defending the disenfranchised or fighting injustice. A privileged woman, who was friendly with a Skadden partner, wanted help setting up a nonprofit related to her dance studio.

How the hell did we get this? Greg thought.

The two office neighbors gave minimal attention to what they considered a waste-of-time undertaking. The high-society lady was so unimpressed with their work that she fired them. Greg was let go by a client who paid nothing. Experiences like these helped sharpen Greg’s ability to see multiple sides of an issue. We’re helping one bullshit corporation get the best of another bullshit corporation, he thought. He understood the good and bad in most sides.

* both disliked the notion that lawyers were easily substituted for one another, viewed as fungible assets.

* Greg was ill-suited for a career as a lawyer. In law school, he got by on his book smarts, but practicing law required keen attention to detail and relentless focus on organization—skills Greg lacked. And he knew it. Greg explained, “If you spend five minutes with me or watch me try to balance my checkbook, you can only imagine the disaster I would make of anyone’s legal issues.” Greg would occasionally show up for assignments with the wrong client’s files. One of his closest friends called Greg the most disorganized person he had ever met.

Real estate law was particularly inappropriate for him. Greg loathed poring through mountains of documents to analyze financial statements, lease agreements, title rights, and other deal minutiae. At Skadden, he would have to take orders from real estate partners before he could do any substantive legal work.

The desk work and the sterile office environment took a toll on Greg’s psyche. Law firm drudgery ate at him. Reviewing documents and dealing with law firm politics nearly broke him.

* “Most people who find out I’m Hispanic, they react the same way: “Like, wow, man, you don’t seem Hispanic.” They say it like it’s an enormous compliment.”

* Greg characterized “Spanish it up” as “a million examples of just fucking horrific retardation.” He mentioned that certain plot lines played off the worst kind of stereotypes. He shared an example of one involving a pregnancy scare with his girlfriend. “I guess they thought that she could be all stiff-upper-lippy and WASPy about it,” said Greg. “And I would be all proud Latino, like, ‘I banged that bitch and I knocked her up!’”

In a People magazine interview, Greg talked about the challenges of representing a culture. “Because I grew up in an Irish neighborhood, I never really identified myself with my ethnicity,” said Greg, who didn’t want to be viewed as “the torchbearer for all things Hispanic” just because he was on TV.

* Greg wanted to replicate the type of stable home life that his parents gave him, but he faced personal issues that made it more difficult to achieve. He couldn’t escape his feelings of inadequacy. Perhaps it emanated from some type of depression, but Greg’s mental distress impacted his family. It also caused him to seek remedies to treat his angst. Alcohol gave him a temporary reprieve.

* Greg and MaryAnn entered couples therapy—this helped Greg come to terms with his addiction and see that it was a diagnosed illness. But there were major challenges to overcome. During a session, the therapist told them that there was no point in going to therapy until Greg treated his own condition.

“You can’t go to therapy if you’re an active addict,” the therapist told Greg. “You’re not even going to remember anything that we’re saying.”

This message hit home for Greg, who felt incredibly guilty about what his family had to endure. It gave MaryAnn comfort, knowing that he had heard it from a licensed professional. Greg worked to improve his health, but he struggled. MaryAnn, who had witnessed her own father’s bouts with alcoholism, wanted desperately to help Greg. But she knew it was his battle to fight. She saw signs that were less obvious to others. She noticed that sometimes Greg’s hands would shake, a symptom of alcohol withdrawal.

As Greg’s drinking issues worsened, MaryAnn stepped up and worked feverishly to help maintain the relationship between her three sons and their father. The situation was serious. The family spent tens of thousands of dollars to send Greg to rehab. MaryAnn, however, thought about much more than just money. “All I want is for the kids to be able to spend time with him,” she said. “Because I don’t expect him to live.”

* [Jay] Dixit wanted to interview a successful comedian. By 2009, Greg had been doing comedy professionally for almost 20 years. Audiences loved him and comedians respected him. From Dixit’s perspective, Greg was the perfect counterpoint to failure. He connected with Greg. What transpired shocked him.

In his interview for Psychology Today in May of that year, Greg revealed that the outward success was not something he felt or saw in himself.

“I’m constantly tortured by a sense of failure,” Greg told Dixit. “I feel like quitting all the time.”

Dixit was surprised not only by Greg’s perception of himself, but by the open, honest, and thoughtful way in which he spoke. In Dixit’s long experience as a journalist, this was rare.

Several times, Greg referred to himself as a “fuckup” and criticized his perceived lack of resiliency. “I’m not a ‘get knocked down and just pull myself back up by my bootstraps and come back harder’ kind of guy,” he said. He admitted to “this constant feeling of not having achieved enough . . . the sense that I suck constantly . . . frustrated with myself and my limitations.”

Greg was not perfect, of course, and some of his harsh self-assessments were accurate. “I’m constantly tormented by the fact that if I could get organized enough to just sit down and write, I would be 50 times further than I am today, creatively,” he said. During his time preparing for Tough Crowd, Greg excelled under the constraints of deadlines and deliverables, but in the less structured environment of a comedy tour, his creative output flagged. He also received regular requests from film executives asking him for movie ideas, but after coming up with some concepts, Greg said, “I get all fucking ADD and the opportunity slips away.”

Apart from the ability to be a disciplined writer, though, Greg had many skills and accomplishments. Comedy clubs wanted him to headline. His peers admired his artistry. Television producers paid to work with him. Still, he criticized himself for falling short of his potential. High achievers such as Greg often hold themselves to unrealistic standards. In one sense, it helps them, it drives them, it pushes them past plateaus. But expectations can get so elevated that they create a constant sense of failure. Greg looked for examples of himself as a failure, and of course he found them. The cycle continued.

“It’s confirmation bias,” Dixit explained. “If you think you’re a fuckup, you’re going to find reasons to justify your belief.”

Greg’s issues with self-confidence became so severe that he wondered if he even deserved to be a comedian. “That was such an insane thing for a guy like that,” said Colin Quinn. “A lot of young comedians looked up to him the most by far as the guy they loved.” Greg worried about the effect of being perceived as unsuccessful, a “loser” whose projects never “take off.” He didn’t care about the lambasting he often got at the comedy roasts—he famously dished it out too—but he did worry that some people might conclude that the jibes about him were actually real.

“It’s not so much the jokes, I just worry that it will become a self-fulfilling prophecy,” Greg said. “Like, great, I’m Greg—the guy that kills fucking pilots. It maybe gets to me on that level. There’s maybe this little part of me that thinks, Fuck, maybe they’re right. I haven’t really accomplished anything they can make fun of.”

In conversations with friends, Greg discussed suffering from the impostor syndrome—an internal experience of intellectual phoniness that researchers say “interferes with the psychological well-being of a person.” The consequences are very real, and those impacted confront fear, stress, self-doubt, and feel uncomfortable with their achievements. The results can be debilitating, and the more success the person has, the more they focus on how much they are below their ideal, “strengthening the feeling of being a fraud or an impostor.”

* Greg became a staunch admirer of comedian Doug Stanhope. He respected how Stanhope always said exactly whatever he wanted to.

* Greg was not afraid to take risks on stage and he didn’t always play it safe with his material. This helped Greg stand out comedically, but the risky material sometimes clashed with his natural empathy. He could be overly sensitive to those who felt alienated or offended by his edgier humor. Many comedians are able to separate the two aspects of their person more categorically. Patrice O’Neal, who famously sparred with him, was one of those. O’Neal could cut hard at any topic or even an audience member, and he always laughed it off and just moved on. It doesn’t mean that he was heartless. He was just more able than Greg was to make the separation between what he was performing on stage and how it might affect the person he was talking about.

As an example, Greg and Schrank made a series of online videos, with one involving Greg interviewing a supplier of communion wafers used for the Eucharist in Catholic church services. Greg asked if the wafers came in different flavors, such as jalapeño for Latinos. This bit caused someone from his high school to send him an angry email. Greg took the criticism to heart. He worried that he had offended the entire Regis High community.

* In an infamous exchange between Greg and Denis Leary on the show, Leary himself remarked about Greg’s preparation. The incident occurred on May 7, 2003. Greg and Leary joined Lenny Clarke and Sue Costello on the Tough Crowd panel. Quinn steered the conversation to North Korea. Rumors had circulated that the country was developing nuclear weapons and pointing them toward the United States.

The comedians threw around suggestions on how to mitigate Kim Jong-il’s destructive tendencies while cracking jokes about his drinking habits and diminutive stature.

“Do you know how short you have to be to have a Napoleon complex in North Korea?” joked Greg about the five-foot-three dictator.

Moments later, Leary more sternly endorsed an American military action against the communist nation. Greg commented that “maybe there’s a nonviolent way to solve the whole North Korea thing.” Leary interrupted and mocked Greg’s point by proclaiming, “There’s a nonviolent way to solve a problem with the country that we hate, that hates us, that’s got weapons pointed at us? I don’t think so.”

Without hesitation, Greg replied: “No, you’re right, like Russia, for example, that big Russian war.”

The audience went silent—processing the sharp comeback—then laughter broke out in the crowd. Meanwhile, Leary looked at Greg stone-faced, pointing his left index finger in Greg’s direction.

Moving on with his planned material, Greg proposed that the two nations could temper their grievances by offering economic concessions: “I heard they’ll agree to stop building nukes if American women agree to get their nails done at least twice a week.”

Leary—displaying no reaction to the manicure joke—accused Greg of over-preparing. “This guy writes so many jokes before the show it’s not even funny,” said Leary. ”Unbelievable. He’s got, he’s got a pocket full of them.”

“That’s kind of what we do here, Denis, a little comedy writing,” said Greg. This line caused the fatherly Clarke to shout, “I’m not coming back.”

Leary countered: “You’re the guy in school who did all the homework and then asked if there was any more that needed to be done.” To which Greg snapped: “And if you had tried a little comedy writing, maybe your show would still be on the air.”

The atmosphere flipped from comedic to combative. With the two alpha males engaged in trash talk, Quinn set one foot on the coffee table that separated Greg and Leary, to play peacemaker. Quinn then said that the segment was over and alluded to a possible scuffle that might take place on the set. Before the lights faded out Quinn said, “This is as ugly as it’s gotten, and it definitely gets ugly on this show.”

This exchange between Greg and Leary has gone down as an epic moment in the annals of comedy lore. Comedian Steve Hofstetter called it “one of the greatest things I’ve ever seen.” Maron said, “There’s no better moment of television that I can imagine.”

Once the episode returned from commercial break, no ugliness or tension lingered. The comedians appeared undisturbed and joked almost dispassionately about fraternity hazing.

“Fraternities are great,” said Greg, referencing his college days. “If you get drunk and pass out, there’s always someone to pee on you.”

So why were things so calm? Details behind how the altercation went down add to its mystique. The portion of the show involving North Korea was a replacement segment and not part of the original taping. Quinn considered the first version too “boring” and requested a reshoot. The exchange between Greg and Leary was taped last but aired early in the show. So the reordering gave the appearance that nothing had carried over from the fight between Greg and Leary.

* As for Leary, he was more objective about the incident. “It was a great moment, where I really looked like a douchebag,” he said in an interview almost eight years after his appearance on Tough Crowd. “And I felt bad. In Greg’s defense, he actually—he was very prepared for almost anything that could have happened.” Quinn granted Leary the opportunity not to air the segment. Leary, however, insisted that it stay in, telling Quinn: “That was good TV.”

* Greg: “Of course blacks watch more TV: there’s not a hell of a lot to do in jail.”

* Greg responded: “The people that are in the media that review shows are a certain kind of upper-class, elitist type of person. They have a certain view of comedy. This show was more in-your-face, very blue-collar, down-to-earth, honest, not ironically distant, and they didn’t know what to make of it.”

* [Nick] Di Paolo: “Last night I was at The Stand, a club in New York, a little tiny club in there, smaller than the friggin’ Comedy Cellar. There’s two black gentlemen up front probably older than me. They had suit jackets on. They fucking loved me. I made a couple cracks about the riots in Baltimore. The rest of the room was fucking Johnny White NYU students. They’re getting all nervous and clamming up. The two black guys are howling. I’m talking to them. I said, “Look around,” to the black guys. I said, “Look at all the white kids afraid I’m going to hurt your feelings.””

* Jim Gaffigan also commented on the amount of rejection in show business and characterized the effect it can have on a performer as a “tax” quite unlike anything experienced by anyone in a regular profession, such as being a lawyer, where objective hard work and long hours will eventually get you the success, the money, and the partnership that you strive for. “In the entertainment industry,” Gaffigan said, “the rejection, the television show that didn’t work, the second television show that didn’t work, the five or six Comedy Central shows that didn’t work—there’s a tax to that.”

There was an extra shock in this for Greg because he had a pattern of success since childhood. He was successful in grade school and college and even in law school. That changed when he was in his late 20s and trying to break into the comedy business. The failures were difficult to stomach. “He was a great comedian,” said Gaffigan. “But his track record would have told him that he might not be a great comedian.”

* Dr. Ildiko Tabori, the in-house psychologist that Masada hired, has a unique perspective on the range of issues that impact comedians. She is a licensed clinical psychologist specializing in matters of the brain and behavior.

According to Dr. Tabori, addiction is not an independent affliction, unrelated to the rest of a person’s life. It is a coping mechanism. Happy people don’t abuse drugs. “If things are going great in your life, you’re not going to be smoking crack,” said Dr. Tabori. “Substance abuse does not exist in a vacuum.”

Dr. Tabori followed Greg’s career, and she noticed that the subject matter of his material seemed to reflect his mental state. “You can see him starting in a really great, positive place and being really successful,” she said, “and then things went awry. I don’t know what was necessarily going on in his personal life but you can see it in his comedy where he started to get really, really angry on stage, and it was dramatic, the difference.”

She surmised that most of Greg’s mental struggles didn’t start with drug use. “He was doing drugs because he was sad and depressed,” said Dr. Tabori.

She also speculated that a desire to perform often has more to do with low self-esteem than confidence. Some comedians view the stage as the only place where they can get attention. “And if they’re not center stage, they’re not comfortable and they start feeling those self-doubts,” said Dr. Tabori. “Somebody who is feeling secure doesn’t always need to be the center of attention.”

When it came to addressing the causes of his angst, Greg thought initially that alcohol and drugs helped him cope. He said: “I’m actually fixing my problem. I’m treating my illness.” Then he quickly learned that this approach didn’t work. “And then you try to stop, and not drink or anything, and all of a sudden that illness is still there with no medicine,” Greg said. “It gets fucking worse and worse and worse—until you address what’s wrong with you, then you’re going to keep picking up and going back down that path.”

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