🎙 The (Misunderstood) History of Skip Bayless

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By the age of five, he claims he was already raising himself.

By the time he graduated high school, he had earned a full-ride scholarship to one of the country's most prestigious universities and was winning national awards for his journalism. 

But now Skip Bayless is being called the most hated man in sports, less than 15 years after he changed the industry forever.

So how did he get here?

And what was Skip’s secret to going from the child of two parents who said they never wanted him to becoming one of the most iconic figures in sports media history?

Because there was a specific strategy he used to achieve this meteoric rise, and it’s the same thing that’s now responsible for his downfall.

We’re about to find out, and by the end of this newsletter, I’ll share the only way I think Skip Bayless can salvage his career.

Because it is still possible, and he just won’t like hearing it.

• ✏️ Background

• 📚 Signs of Promise

• 💫 Rising Star

• 💫 Rising Star

• 🎙 First Take

• 🎙 First Take

• 🔮 Predictions

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✏️ Background

Family Life: John Edward Bayless II was born in Oklahoma City in 1951 to Levita and John Sr.

Almost immediately, his dad started calling him Skip, which was short for Skipper, and also his mom's nickname.

In fact, Skip recalls never once hearing his parents call him by his birth name, John, which bothered him so much that by the time he was 20, he legally changed his name to Skip.

Now, his mom earned this nickname because she was the head of the Bayless household, and as the oldest of his three siblings, young Skip took after her in many ways, and not all of them were good.

Skip's parents owned a barbecue restaurant called the Hickory House in OKC, where he began working at the age of four.

It was here that he began to describe his mom as a vain, self-absorbed woman who told him many times to his face that she never wanted to be a mother.

Meanwhile, his father was an abusive alcoholic who rarely said more than a few words per week to his kids.

This upbringing meant Skip was “pretty much on his own starting at age 5, which made him resent almost everything about his childhood — to the point that in his 20s, he vowed never to have kids of his own for fear of turning into either one of his parents.

Childhood Aside from his family life, Skip’s childhood can be described as fairly typical.

He fell in love with sports at an early age, particularly basketball and baseball, and while he was better at baseball, he says that basketball became his first love.

However, he stopped growing in high school at 5’11”, which meant he had to rely on his ferocious competitiveness to make his high school team — the same competitiveness that often landed him in fights at a young age.

When he reflects on it, Skip blames his dad for giving him, as he describes, a Type A+ personality since he grew up always thinking that he had to prove his dad wrong.

That’s because, aside from drinking, his dad’s favorite hobby was being disappointed in everything he did. To this day, Skip can’t recall one time either of his parents ever asked how he was doing in sports or school or told even him that they loved him.

This stoked a fire in him at a young age that can actually still explain some of his actions today, but early on, it simply meant that Skip became solely focused on one goal:

Leaving Oklahoma City and going to college.

Up until this point, no one in his family had more than a high school education, and Skip thought that his ticket out of that cycle would be through basketball. However, in his senior year, he only averaged 1.4 points per game.

Luckily, he had a hidden to fall back on - he just didn’t realize it yet.

📚 Signs of Promise

High School: As Skip tells the story, one day during his junior year, his English teacher asked him to stay after class.

He describes how she didn’t ask but rather ordered that he join the journalism club because of his promising writing skills.

Skip objected, but to no avail, and that year, he began covering the very same teams he was playing on.

This led him to earn a sportswriting scholarship that allowed him to attend Vanderbilt University on a full-ride.

College: Here, he majored in English and history — only calling home a few times per year. He was happy to have escaped Oklahoma City, and by 1974 he graduated cum laude and took a job working at the Miami Herald.

💫 Rising Star

Early Career: Early in Skip’s career, he became well-known for his investigative work as a sports columnist who never shied away from covering potentially touchy stories.

For instance, in 1976, when he took a job at the Los Angeles Times at just 25 years old, he made a splash when he published a piece on the Dodgers’ clubhouse resentment of their “golden boy” first-baseman Steve Garvey and his celebrity wife, Cyndy.

Another time, he ruffled feathers when he reported that LA Rams’ owner, Carroll Rosenbloom, was actually the one making the behind-the-scenes decisions to start different quarterbacks every week.

Skip’s stories were part sport, part reality TV, but they were always well-sourced, expertly written, and extremely in-depth, often 3,000-4,000 words long.

He even won his first National Award for Outstanding Writing in 1977 at age 26.

The same year, he became one of the youngest sports writers to have a national column at the Dallas Morning News and later the Dallas Time Herald.

Here, he would go on to be voted Texas Sportswriter of the Year three times between 1979 and 1986, but then, in 1989, Skip would publish a story that would set his career on a crash course no one could have predicted.

Early Controversy: Skip’s rise to fame in Dallas coincided quite well with the Cowboys' rise in popularity, and in 1989 and 1993, he wrote his first two books chronicling the team’s rise.

Both pieces featured the exact kind of work Skip had become known for; they were well-sourced and in-depth but contained the kind of salacious drama that helped them fly off the shelves.

That’s when Skip took things one step further and published his third and final book in 1996, titled Hell-Bent: The Crazy Truth About the "Win or Else" Dallas Cowboys after their third Super Bowl win in 4 years.

But this last book contained a section that drew major scrutiny at the time and is something that still follows Skip around today.

Skip learned that controversy and drama sold, and nowhere was there more drama with this Cowboys’ team than between head coach Barry Switzer and star quarterback Troy Aikman.

In the book, Skip reported on speculation by Switzer and people close to him in the organization that Troy Aikman was gay.

And while Skip himself never claimed to believe it, his mere reporting on whether or not it was true caused national outrage.

This tabloid style of writing that Skip had become known for only solidified him as one of the most polarizing figures in Dallas—especially among his fellow sportswriters, who felt that he was just being controversial to drum up sales.

But Skip didn’t care because he had been proven right:

Controversy Sold.

The book was a hit, and he was even able to start faxing his column directly to readers for $99 a year when his employer, the Dallas Times Herald, went out of business, but what really solidified Skip’s identity as a contrarian was when a relatively new 24/7 sports network came calling.

📈 Moving Up

ESPN: The same year Skip published his first book (1989), he also joined ESPN as a panelist on their show, The Sports Reporters.

By then, he was already well-known locally as a polarizing figure, but now he was given the platform to talk about more than just the Dallas Cowboys—and he took it.

By the 2000s, Skip had made the leap from the newspaper to completely focus on TV, spending the next few years guest-starring on different ESPN shows, filling in for Jim Rome, and even commentating events for the Golf Channel.

In 2004, ESPN finally hired Skip full-time to team up with Woody Paige in a daily segment called “1st and 10.” The idea was that the two reporters would be featured during ESPN2’s new morning show, Cold Pizza, and asked to debate a few topics every day in between news and highlight segments.

But that version of the show wouldn’t last long for two reasons, both of which have been blamed on Skip.

The first is because, according to his co-host Woody Paige, Skip was tiring to work with. He had always been a loner, even during his days in Dallas, but his obsession with his job was beyond what anyone else was used to.

And that’s not just coming from me:

But while this dedication might have served Skip well at his previous jobs, talking a light-hearted TV debate segment too seriously became his specialty - to the point that it resulted in a physical altercation with his co-host, Woody Paige:

Now, other people familiar with this incident say that Woody is playing it up a little bit, but the tension was certainly real, and whether or not it’s the reason Cold Pizza only lasted three years, what you can’t refute is that Skip was the architect behind what came next.

🎙 First Take

The Launch: In 2011, almost four years after Cold Pizza was canceled, a show called First Take was launched to replace it.

However, this show wouldn’t have any of the segments or highlights that normally came with an ESPN morning show. Instead, it would be built solely around the most popular part of the program it was replacing:

The Debates.

And at the center of it would be ESPN’s most polarizing personality, Skip Bayless. Immediately, the show was a success, seeing a 58% increase in ratings in just the first three months.

After cycling through different debate partners for six months, the network decided to make another emerging star, Skip’s permanent co-host, a local NBA reporter from Philadelphia, Stephen A. Smith.

This decision launched the show to an entirely new level, with First Take regularly averaging close to half a million viewers per episode — making it the most viewed original program on the network.

But just like before, Skip’s overly serious attitude and his knack for provoking controversy created a rift that proved too much for him to overcome.

The End: Now, it’s hard to pinpoint the exact moment that Skip Bayless jumped the shark - but one example could be his tireless coverage of Tim Tebow.

From claiming Tebow was a better prospect than Andrew Luck in 2012 to saying he would take him over Tom Brady and Aaron Rodgers with the game on the line, Skip found a way to shoehorn Tebow into every sports debate, even long after he was done playing football.

And evidently, this schtick grew old quickly with the bosses at ESPN:

But none of this phased Skip - because he was doing the thing he was best at:

Stirring the pot.

And now he was doing it on the biggest network, with the biggest show in the country, and he was about to receive a call that would validate all of the work he had been doing for the past 40 years.

💰 Undisputed

Joining Fox: In 2015, Fox was trying to build out its sports department so that it could finally rival ESPN.

To do this, they eyed some of their competitor's best talent, including a four-year, $20 million deal with Skip to create a similar debate-style show to challenge First Take's success.

And if Skip wasn’t already stuck his ways before this big payday, he definitely was now, and you can’t blame him.

He was now making more money than he probably ever had in his career to do the one thing he had become most famous for:

Debating sports on TV.

In 2016, FS1’s Undisputed premiered with former NFL TE Shannon Sharpe sitting across from Skip, but this proved to be the beginning of the end.

In its first full year on air, the show barely averaged more than 120,000 viewers—four times less than what First Take was pulling.

But Fox doubled down on the format, re-signing Skip to another 4-year, $32 million deal in March of 2021. However, the slide continued, and after a public fallout between Skip and Shannon in 2023 sent Shannon packing for ESPN, Undisputed has failed to average over 100,000 viewers since.

So it’s no surprise that when Skip’s contract was up for an extension this year, the network decided they were okay with letting him walk.

But that doesn’t mean Skip is done, because even though it may look like the 72-year-old’s best days are behind him, just listen to him talk about retirement a few years ago:

That doesn’t sound like a guy that’s ready to pack it up… so what should he do?

His own podcast isn’t all that successful, and ESPN doesn’t seem to want him back.

Well, I have two predictions: one is what I think he should do, and the other is what I think he will do.

🔮 Predictions

What He Should Do: At this point, Skip has likely earned over $100 million in his career, redefined sports media for better or for worse, and become a household name.

I think even he’d admit that’s more than he could have ever hoped to accomplish.

But at the same time, it’s clear that he’s not ready to sit on the beach until he dies, so why not go back to his roots and write another book on the Cowboys or as a memoir?

His name recognition alone would make whatever he writes an instant best-seller, not to mention that writing is arguably what he’s best at. This way, he could still be involved in sports, but it could happen on his terms—without the need for all the politics of a big network.

And he can ride into the sunset as a pioneer in sports media while being remembered for his true talents.

But if I were to put money on it, that’s not what’s going to happen.

What He (Probably) Will Do: Instead, I could see some second-rate media network or even a local radio station offer him a cushy yet discounted salary to spit takes on their channels until he can’t walk anymore.

This would certainly be the saddest option; it would be like watching a washed-up rock star play at a county fair.

It’s sad and demoralizing, and it's probably where he’ll end up.

Because at the end of the day, Skip always got attention for his sensationalized takes and ideas, not any connection he’s built with an audience.

And when he wasn’t the only one debating sports on TV anymore, his audience realized there were better places to go for sports content.

Leaving him on the outside looking into an entire industry he’s responsible for helping create.

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