Jon Gruden: Drawing Up Deals Instead of Plays

November 09, 2025

Welcome to Gridiron Wallet — where NFL players don’t just chase rings, they chase bags. From million-dollar grills to side hustles that slap, we’re decoding how football’s finest make it, spend it, and sometimes… fumble it. 🏈🔥

The latest edition of our newsletter covers Jon Gruden:

  • Ownership: Arena Football Stake

  • Media & Brand Platforms

  • Real Estate & Financial Portfolio

✍️Paper Play

Media, Platform & Personal Brand

Jon Gruden joined the ownership group of the Nashville Kats, an Arena Football One (AF1) team, in May this year. AF1 is a professional arena football league based in Nashville, Tennessee. With this latest investment, Gruden has pretty much done everything there is to do in the game of football. Except play, that is. Nobody can have it all, right?

But Gruden, with his trademark Chucky snarl/smile, has done just about everything else. He was an assistant coach in the college and pro ranks for about a decade from the mid-1980s to the mid-1990s. He had stops with the 49ers, Packers, and Eagles before earning his first head coaching gig with the Oakland Raiders from 1998 to 2001.

Gruden was then traded to the Tampa Bay Buccaneers in one of the most unique deals in NFL history. He promptly won the Super Bowl in his first year in the Cigar City, forever cementing himself as a quality coach. This, even though the rest of his tenure in Tampa was not great, going 45-51 from 2003-2008. He did, however, win two more division titles.

After his departure in 2008, Gruden was almost immediately hired by ESPN to serve as their color commentator for Monday Night Football alongside play-by-play man Mike Tirico, and later Sean McDonough. During this time, he started a football think tank called the ‘Fired Football Coaches Association,’ which attracted the likes of Urban Meyer and Sean McVay. 

Gruden was a well-liked analyst, and his think tank was a success. But he never shook that coaching itch. 

So, after six years of prodding by Raiders owner Mark Davis, Gruden relented in 2018 and returned to the Bay Area on a 10-year, $100 million contract. His drive to compete just wasn’t being fulfilled in the commentator’s booth. His second stint didn’t start well or end well, though. He went 22-31 across 3+ seasons before getting fired due to an email scandal.

After a few years on the shelf, Gruden returned to the public eye in 2024 as a contributor for Barstool Sports. He has fit in there perfectly, adding a level of football expertise and knowledge to the usually comical sports media empire. Which is not to say Gruden hasn’t brought the comedy as well. He might be one of the funniest guys they have on the roster.

But just over a year later, it is once again clear that his competitive nature is gnawing at him to get back on the team side of things. 

Perhaps that’s why he joined the ownership of the revived Kats (formerly of the Arena Football League, now competing in the AF1). He will also serve in consulting and advisory roles on both the business and football sides of things at the club. They finished their inaugural 2025 season by reaching the semifinals following a 3-4 regular season record. 

We’ll see if Gruden can bring some of that Chucky magic to Tennessee that we haven’t seen since 2002.

💸 Future Proof

Startup Investments & Equity Stakes

After his coaching tenure in the NFL, which spanned 12 seasons, Gruden started his own YouTube channel where he provided in-depth analysis of key weekly games. This venture caught the attention of Barstool Sports, which led the media giant to sign him to a multi-year contract in 2024. The best part: If he ever wants to get back into coaching, he has an opt-out clause in the contract that allows him to leave should an interesting offer come along.

Gruden’s presence has now expanded into the digital space, including podcasting and commentary. At Barstool, Gruden follows NFL games on live streams and offers his take. He also still maintains his classic ‘Gruden’s Grinders’ segment that fans love. 

During his time at ESPN, Gruden hosted a hit series called ‘QB Camp,’ where he sat one-on-one with some of the top QB prospects from that year's draft. While at the Worldwide Leader in Sports, he hosted the show for six seasons until 2018, to great success.

Now at Barstool, the company has decided to revitalize Gruden’s once-popular QB Camp series. He has already sat down with prospects like Jaxson Dart and Will Howard, and both of those videos ended up crossing 1 million views.

The series has allowed Gruden to continue building his personal brand, which can feed into business ventures beyond the field. Altogether, Gruden has created a diverse income stream, earning from coaching in the NFL, endorsements, and media appearances. 

Overall, these platforms provide Gruden with leverage for future business and investment opportunities by enhancing his visibility and network. This likely influenced his partnership with the Nashville Kats arena football team and his role as an advisor.

💡 Gridiron Wallet Trivia

Did you know?
🌿 Jon Gruden signed a 10-year, $100 million contract with the Raiders in 2018—then the richest coaching deal in NFL history. Though he resigned in 2021 after email controversies, Gruden reportedly walked away with over $40 million from the deal, making it one of the most lucrative partial payouts ever for an NFL coach.

🏈 ✨Dream Scheme

Real Estate & Financial Portfolio

Gruden’s firing from the Raiders in 2021 and the ensuing email scandal have left a big stain on his coaching career. But since then, the Super Bowl-winning coach has been quietly rebuilding his portfolio and fortune.

Let’s start with how Gruden handled the aftermath of his abrupt exit from that 10-year, $100 million deal. Just months after stepping down in 2021, he listed his custom-built Las Vegas estate for $7.5 million and sold it almost instantly. He had purchased the home for $4.3 million, earning a profit of roughly $3.2 million, before taxes, within a year.

While some may argue that Gruden got lucky with the quick sale, it must be acknowledged that the estate was a piece of art. 

It was located in the exclusive Southern Highlands community. The 8,684-square-foot property boasted five bedrooms, floor-to-ceiling glass walls, a climate-controlled wine room, a gym, an infinity-edge pool, and every other amenity one would expect from the home of an NFL head coach at the peak of his career. 

By the time the sale closed, Gruden had no reason to stay in Las Vegas because he already had a home waiting in Tampa. However, it’s hard to ignore how the scandal affected his public image. 

Once a highly marketable media face, Gruden had endorsement deals with Hooters, GoPro, Corona, Nationwide, Dunkin’ Donuts, Bridgestone, and GMC. He was also one of ESPN’s top-paid analysts during his Monday Night Football tenure, reportedly earning $6.5 million per year. 

As one would imagine, all those partnerships ended overnight after the email leak. But Gruden’s story didn’t end there. 

Now, nearly five years later, the 61-year-old has re-emerged in the public light, joining Barstool Sports in 2024, and also launching his own YouTube channel featuring football breakdowns in his signature ‘Spider Y2 Banana’ style. 

Despite all the setbacks, Gruden’s wealth today stands at an estimated $30 million. This is perhaps due to how well he diversified his income rather than solely relying on his coaching money.

Between his NFL earnings, broadcasting salary, endorsements, real estate profits, and sports ownership stake, he quietly diversified his assets across multiple fronts. The controversy might have cost him his legacy, but not his financial acumen.

📆 NFL Money Stat of the 1940s

In the 1940s, the average NFL player earned around $5,000 per season, but many made far less—especially during World War II, when rosters were depleted and teams merged to survive (like the “Steagles” in 1943). Meanwhile, franchises were valued under $150,000, a fraction of today’s multi-billion-dollar NFL team valuations.