Jon Gruden’s legal battle with the NFL has now landed in the Tampa area, where the former Buccaneers coach still has deep ties and where four people close to him are pushing back hard against subpoenas tied to the case.
Court records show those four - Hooters co-founder Ed Droste, ReliaQuest Bowl President/CEO Jim McVay, Gruden’s wife, Cindy, and Jeff Leonardo, who worked as an assistant to Gruden during his time with the Raiders and ESPN’s “Monday Night Football” - are fighting requests to hand over 15 years of private communications with Gruden. Droste and McVay filed separate objections in Hillsborough County’s 13th Judicial Circuit Court, but the language in both filings is the same.
Their argument is straightforward: Gruden’s lawsuit over an alleged retaliatory leak does not open the door to a sweeping dive into his personal life. “Jon Gruden’s suit challenges an alleged retaliatory leak and the resulting losses,” the filings from the two Tampa Bay businessmen read. “It does not justify an unrestricted examination of Jon Gruden’s character.”
That discovery fight is part of a much bigger case Gruden brought against the NFL and commissioner Roger Goodell in Nevada after the 2021 email scandal blew up his coaching career. At the time, Gruden was leading the Las Vegas Raiders on a 10-year, $100 million contract when the Wall Street Journal and New York Times reported on emails in which he used homophobic, misogynistic and racist language over a seven-year stretch that ended in 2018. Those emails had surfaced during a league investigation into workplace misconduct within the Washington franchise.
Gruden resigned in the wake of the reports and has not coached since. The next month, he sued the NFL and Goodell. His attorney, Adam Hosmer-Henner, accused the league and its commissioner of leaking Gruden’s private correspondence to the two newspapers “in order to harm Gruden’s reputation and force him out of his job.”
The Nevada courts have already given Gruden a major procedural win. In August, the Nevada Supreme Court turned down the NFL’s bid to send the case into the league’s arbitration process, which is overseen by Goodell.
Then in October, the court unanimously rejected the league’s request for a rehearing. That means discovery moves forward - exactly what Gruden wants as his lawyers try to prove the emails were selectively and strategically leaked.
But that same process also puts Gruden’s private communications under the microscope. And those messages already have done serious damage.
In the emails reviewed by the Wall Street Journal and New York Times, Gruden used a homophobic slur to describe Goodell, invoked a racist trope in reference to then-NFL Players Association executive director DeMaurice Smith and wrote that Goodell should not have pressured the then-St. Louis Rams to draft “queers” after Michael Sam became the first openly gay player selected in the NFL Draft.
He also exchanged emails with Bruce Allen, then president of the Washington Football Team and a former Buccaneers general manager, that included photos of women wearing only bikini bottoms, among them one image of two Washington cheerleaders. In another email, Gruden said former 49ers safety Eric Reid, who knelt with Colin Kaepernick during the national anthem in 2016 to protest systemic racism, should be fired.
The NFL is now pressing for more of Gruden’s private material, and in October attorney Laura O’Boyle told a Nevada judge that Gruden is “delaying discovery and giving us half answers,” according to a transcript obtained by Sportico.
Gruden’s public profile, meanwhile, has surged back in Tampa Bay and beyond. He was inducted into the Bucs Ring of Honor in 2017, then removed shortly after he stepped down with the Raiders.
Since joining Barstool Sports in November 2024, he has reemerged as a familiar and popular figure. His X account, launched when he joined Barstool, now has more than 435,000 followers.
He has also been visible around the Tampa Bay sports scene, with appearances tied to the Rays and Lightning during their recent playoff runs, visits to USF’s football facility and a role as grand marshal for the 2026 Firestone Grand Prix of St. Petersburg.
In February 2025, the Buccaneers put him back into their Ring of Honor, and in September Shear Media Studios announced Barstool would use its St. Petersburg studio to produce a weekly football show.
For now, though, Gruden’s effort to pry into the NFL’s handling of the emails comes with a cost: the same discovery process he’s been fighting for could keep exposing the private correspondence he’d rather keep buried.
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