Gilbert Arenas is the past, present, and future of sports content

This article was published in conjunction with the 2025 Awful Announcing Sports Podcast Power List. To read more about the sports podcast and digital video space and the people guiding it right now, click here.

For as long as there have been people whose jobs are to entertain audiences, there have been people like Gilbert Arenas.

Throughout his 11-year NBA career, it often felt as if Arenas was only on the ground floor of what he could be as a player. Ahead of the curve in jacking three-pointers and a generation early as a big playmaker, Arenas won the long game, proving that scoring guards could thrive in the league. A few years into his time in the media game, the feeling is the same.

Arenas, who hosts live daily shows under The Arena banner at Underdog multiple times each week, doesn’t even see himself as a podcaster. When I called Arenas for our scheduled interview, he was playing NBA 2K live on YouTube. He answered on speaker phone, stream still going, before laying out all the ingredients that have made him one of the most successful entertainers in sports media in a few short years.

“A podcaster is really just an interviewer. Most podcasts, you’re only entertaining because of your guests,” Arenas told me. “If your guest is an entertaining guest, you’re going to do numbers. Versus me, I am the entertaining guest.”

With entertainment as the North Star, Arenas has built The Arena into a powerhouse in digital sports content. The show, which recently added a twice-weekly NFL offshoot featuring Skip Bayless and Aqib Talib, boasts nearly 1.2 million subscribers on YouTube and nearly 400,000 followers across TikTok, Instagram, and X. Add in another 1.3 million followers for Arenas himself. According to Underdog, The Arena is nearing 1 billion total views since launch and has generated $10 million in YouTube programmatic revenue.

The idea that would become Gil’s Arena began a few years after Arenas retired from the NBA, when he linked up with Complex to launch a podcast. Arenas hardly paid much attention until his producer started posting episodes to YouTube. “I’m famous, so I would rather show my face,” Arenas told me. Interviews began to go viral, and eventually FuboTV picked up the show.

Around this same time, Arenas met a serial media entrepreneur named Tim Livingston. When Livingston worked at Yahoo, he wrote a profile of a celebrity painter named Art Mobb, whose real name is Mike Farhat, and who also sold to Arenas. In return, Farhat promised Livingston some help down the road if he ever needed it.

Aware of Arenas like any other sports fan, Livingston went from admirer to disciple in 2016, when he watched a viral Snapchat video of Arenas breaking into the home of Los Angeles Lakers guard Nick Young. In a series of story posts, Arenas interrogated Young about infamously cheating on rapper Iggy Azalea. In between, Arenas made a point to wreck Young’s son’s play area and harass the Youngs while they played basketball outside.

“It was just ridiculous, but I also thought the storytelling was brilliant,” Livingston told me. “One of Gil’s superpowers is that he really doesn’t give a f*ck.”

Seeing the videos rocket across the internet, Livingston cashed in the favor from Farhat. After hitting the painter up once again, Livingston walked away with a custom painting of Jason “White Chocolate” Williams — and a direct line to Arenas.

The two met for drinks at Honor Bar in Beverly Hills. While waiting two and a half hours for a tardy Arenas to show up, Livingston contemplated the future of sports content. Even three drinks later, he felt strongly it would look a lot like Arenas. And he hoped Arenas would trust him to lead the way.

“I thought I would never hear from him, and then I got a call the next day from an 818 area code, and it was Gil,” Livingston recalled. “Gil got really passionate and really into it, and now really loves the strategy component of all of this. How to dominate on YouTube, how to scale all his different socials, TikTok trends, all of it.”

This was a time, in the late 2010s, when our current era of digital content was just beginning. YouTube was established, but new platforms like Twitch and TikTok were fresh on the scene to not only compete with YouTube but to give creators new ways to broaden the connection they could build with their communities. Essentially, to give creators a chance to be in their fans’ lives 24/7. Arenas studied what worked, from MrBeast contests to drama reaction videos to, eventually, live streams.

In the sports world, there was just one person who seemed to understand the potential of a live, daily YouTube show.

“Most sports shows were pre-recorded, so they could tape it, produce it, take out what they want, make sure it’s all clean,” Arenas said. “Then I came across Pat McAfee.”

In short order following his own retirement, McAfee had taken The Pat McAfee Show from a radio curio to a pioneering smash. With a crass tone and a tireless, obsessive passion for football, McAfee built the show in his own image and audiences flocked to him.

During the public health shutdowns in 2020, audiences tuned into live streams at record levels, quickly making YouTube and Twitch into legitimate replacements for radio and daytime television. McAfee was on the brink of cashing in with Disney, and Arenas knew he could mimic the former punter’s formula.

Having stayed in touch with Livingston, who was now running content at a fantasy sports gaming company called Underdog, Arenas had a vision.

“There’s no basketball version of this McAfee stuff, there’s no YouTube version of Inside the NBA. When I was talking with Underdog, that was the pitch,” Arenas told me.

“We’re going to be the next Pat McAfee. There’s no one else in the space. All the other basketball players are once a week, pre-recorded. We go live three, four, five times a week, we are dominating the space. Everything is moving to, who can push out the most content? If you’re pre-recorded, you’re behind.”

Underdog rewarded Arenas with equity and 50 percent ownership of the show that would become Gil’s Arena. The company helped build Arenas’s studio in Los Angeles, where he, NBA Twitter jokester Josiah Johnson, and fellow NBA retirees Kenyon Martin, Rashad McCants, and Brandon Jennings cycle between ripping one another and talking hoops each day for two to three hours.

When Arenas partnered with Underdog as one of its first acquisitions, the company was valued at $485 million. After its latest investment round earlier this year, the valuation leapt to $1.23 billion. Originally a fantasy sports company, Underdog now offers legal sports betting and prediction markets. Since launch, it has used content partnerships to drive sign-ups and engagement for its core games product. Other hosts include Cam’Ron and Ma$e, Josh Norris, and Jared Carrabis.

Those are the relevant facts. Yet if you watched Arenas on the come-up or hear how he thinks, they are merely the particular details of how, in this timeline and in this universe, the inevitability of Gilbert Arenas, media star, came to be. Arenas was bound to be a sensation. This is a man who blogged for NBA.com and tried a podcast before Matt Barnes, JJ Redick, or Draymond Green. Who gleefully filmed a video dancing down the steps of a federal courtroom just three months ago. Arenas was sure to be a media star because he is a tireless worker and diligent student, but also because he knows how people tick.

“People are looking at the wrong data,” Arenas told me. “People are not looking for entertainers. They are looking for names. They think that someone’s NBA credentials are going to bring them an audience.”

https://youtu.be/HHx8fJ03FhI?si=0Ro5idwcd9rXsplL

A new athlete podcast launches seemingly every week. Active and retired players threaten to take over the whole sports media industry. What Green once called New Media is just media now.

Yet Arenas is a throwback. In our conversation, he compares himself to Kevin Hart. They both are just as comfortable on a traditional television or movie set as on a Twitch stream or TikTok video. But Arenas is also in a lineage that includes Jim Rome, Dave Portnoy, and Deion Sanders. Stars who love to hear themselves talk and never tire—one-stop shop entertainers who can deliver day in and day out for an audience in perpetuity.

In 2025, that means keeping up with younger people and speaking the lingua franca of the internet. That’s why Arenas streams video games, argues over the news of the day from r/NBA or NBA Twitter, appears on First Take, and even recently started talking football on The Arena: Gridiron. If there’s anyone who is on-air as much as McAfee these days, it may well be Arenas.

The core of Arenas’ popularity and his idea about how to win at sports media and where it is going, though, is still Gil’s Arena. The show is about basketball, in theory, but really it is about what happens when a bunch of highly opinionated former hoopers get together and bicker. Other shows claim to recreate the locker room through stories and laughs; Gil’s Arena does so by unwaveringly showing grown men argue until their faces turn blue.

Arenas is liable to make an outlandish trade demand, slice through the greatness of an MVP, or compare himself favorably to living legends, and then wake up and do it again the next day. If it ever feels like he is doing it just to spur frustration or drive debate, you’re gosh-darn right.

To get a sense of how deeply Arenas studies virality and television entertainment, consider this nugget of wisdom:

“What I learned being in media is people react to keywords. Phrases. They only hear some of what you’re saying before they want to react. No one listens to everything you say when they’re reacting.”

So, Arenas knows that, for instance, if he says he was better than the historically great Stephen Curry, nobody will listen to the end when he adds the caveat that he was greater before age 25. In this way, Arenas can protect his backside while still enraging his YouTube chat and driving views across the internet.

Jokic is putting up empty stats 🗣️ pic.twitter.com/oM3mQ5ljhp

— Gil’s Arena (@GilsArenaShow) December 10, 2024

As a court jester of NBA commentary, Arenas has seemingly been passed over for jobs at NBC and ESPN. A certain segment of NBA fans despises what he stands for. They lump Arenas in with Stephen A. Smith, Charles Barkley, and the other hosts who make coverage about themselves and their gripes. For many, including most of the new analysts hired as part of the NBA’s new media rights package, comparing Arenas to these supposed has-beens is as bad as it gets. While Arenas accepts these comparisons, he actually strives to go further into the muck than anyone currently working in the industry.

This is where Arenas, thoroughly throwback in his aim to entertain above all else, is actually new-school. Putting the New in New Media.

“The old school thought about it as, ‘Oh my god, my brand, what are people going to think, people are going to be outraged,’” Arenas said. “You’re selling people content. No one boycotts content. They want to see what you’re saying so they can disagree.”

Lately, Arenas has tried to sell content more literally. On a stream earlier this year, he revealed he interviewed to join the NBA on NBC team. Over the summer, Arenas told me, he pitched Netflix and Amazon on licensing or buying his show.

Arenas sold the show not as a companion to Prime Video Sports or NFL Christmas GameDay, but a far different genre category that is even more popular on Netflix in particular.

“We can be entertaining like reality TV for them,” Arenas said.

The problem Arenas encountered was that streamers are more focused on evergreen content libraries than real-time programming. Remember when everyone was watching Suits? While Arenas has built an impressive live daily audience, the rundown for a given show is old news within a few hours.

Still, the Arena team believes the financial model will come around before long. And that the brash, confrontational way in which Arenas and Co. talk sports will increasingly be the modus operandi of sports content creators across platforms.

“Ultimately, the audience is looking for a parasocial experience daily,” Livingston said. “Where they’re at work or on a jog or stuck in traffic on the way home from work, that becomes part of their routine and part of their human experience.”

The ability to own or even partner with a personality as engrossing as Arenas is already enough to get these massive content companies’ attention. One day, the need to compete in live digital content will likely be too strong to pass up on a talent like Arenas.

“Streamers will continue to invest in appointment podcast content,” Livingston predicted. “And what we’re doing and what others are doing in the space, where you have big audiences, big communities that love listening to the content every single day, the daily part of it is so powerful.”

None of this is to say that Arenas represents the Platonic ideal of sports analysis or live entertainment. Even he would agree that he is not. In fact, Arenas would probably say that the thing that others might strive for doesn’t even exist. Or at least, he can wipe it out in a moment with what he does.

“Some of those guys are so professional, yet they’re brilliant and smart. The average audience don’t have that type of intellectual palate,” Arenas said. “So all the brilliance and all the note-taking goes to waste, because I can beat you with an argument of, say whatever, say my opinion, being funny, making fun of you, and then the audience will be like, ‘He’s right.’”

Has Arenas solved sports content? Hardly. He has the stamina and acuity to pursue a well-trodden, lucrative path in a new ecosystem. Antagonizing his cohosts and his audience and all comers? That’s Rush Limbaugh, Howard Stern, and Skip Bayless. That’s Perez Hilton, Keemstar, and Dave Portnoy. That’s cheap and enormously popular. That’s stardom.

What comes with it is scrutiny. Over the summer, Arenas was arrested by federal authorities in Los Angeles for his alleged participation in an illegal, high-stakes poker ring.

His response was to post a video dancing down the steps of the district court in slides and lounge shorts, a big smile on his face. Think Arthur Fleck in Joker.

Among the charges was one count of making false statements to federal authorities. After Arenas appeared to mock the feds in his post, Smith offered Arenas a word of warning:

“When you’re serious and locked in, there’s few on this planet smarter than you bro. When you’re serious and locked in. Not when you’re f*cking around and acting like it’s a joke.”

Back in 2016, Arenas barged into the sports content space just as he barged into Young’s home. Unannounced, chasing an audience. It was the first echo of the charismatic, inexhaustible modern media talent he could and would become. Underdog took the baton and helped build the platform and format that made Arenas shine. The result is The Arena, a true hit and cash cow.

The industry has opened up around Arenas exactly as he envisioned. Suitors are at his door, and he can afford to be picky. While traditional media hold on and attempt to evolve, and athlete after athlete sits down behind a mic, Arenas believes he is the future.

And why not? More than almost anyone else working today, Arenas is taking cues from history’s biggest stars and driving forward into the next chapter of sports content.