Zolak & Bertrand: What exactly is Tom Brady doing?
Zolak and Bertrand can’t help but wonder what exactly Tom Brady is doing these days.

LAS VEGAS, NEVADA – OCTOBER 08: Las Vegas Raiders owner and managing general partner and Las Vegas Aces owner Mark Davis (L) and Tom Brady attend Game One of the 2023 WNBA Playoffs finals between the Aces and the New York Liberty at Michelob ULTRA Arena on October 08, 2023 in Las Vegas, Nevada. The Aces defeated the Liberty 99-82. NOTE TO USER: User expressly acknowledges and agrees that, by downloading and or using this photograph, User is consenting to the terms and conditions of the Getty Images License Agreement. (Photo by Ethan Miller/Getty Images)
Tom Brady's bid for a stake in ownership of the Las Vegas Raiders took a hit this week as skepticism from other owners about Brady's involvement may throw a wrench into the GOAT's plans. With this latest attempt to add to his post-playing portfolio, Zolak and Bertrand can't help but wonder what exactly Tom Brady is doing these days:
'Brady's into some weird stuff'
Zolak: "I found it weird from the get go. You know to be that quickly sort of done with the league from a playing standpoint, but I want to go right into ownership. It was Vegas of all places, like you're in bed with Mark Davis. And just how the percentages were off and what what was really going to be paid? It seems like you're trying to pull a fast one right there to begin with, which gets the owners all on him. You know guy like Curtis Martin. He wanted to be part of a group that owned teams. There's people that have wanted to do this before. Guys wanted to do it. Pete Manning has talked about this. Brady has his hands and his tentacles into so many things. Whether it's F1, whether it's the Electric boat racing. I mean, it's it's World League, Premier League, you name it. His fashion line, whatever he he's got his hands on everything now. It's putting on movies and producing stuff and it was film crews up and running and doing documentaries."
Bertrand: "Brady's into some weird stuff. Boat racing and all these entertainment products that I just look at and say how many of these things have failed? What gets you excited to invest in that? You got all this money. He's into a bunch of junk. He wants to buy up a piece of the WNBA team, which he did. Buys this piece of a soccer team, buys a boat racing team, buys a pickleball team. What is with this? What a weird portfolio. What is all this crap?"
Did a member of 98.5 The Sports Hub date the greatest quarterback of all time, TOM BRADY?
Brady, the now-retired quarterback and seven-time Super Bowl champion, has been making headlines since late last year, not only for his performance on the field but also for his personal life. After announcing his divorce from Brazilian supermodel Gisele Bündchen, the NFL icon has become one of the world's most eligible bachelors, sparking speculations about his dating life. One such rumor involved someone who recently joined Boston’s sports hub, 98.5 The Sports Hub.

LOS ANGELES, CALIFORNIA - JANUARY 31: Tom Brady attends Los Angeles Premiere Screening Of Paramount Pictures' "80 For Brady" at Regency Village Theatre on January 31, 2023 in Los Angeles, California. (Photo by Jon Kopaloff/Getty Images)
Kendra Middleton, co-host of Over/Under 98.5 alongside Dan Lifshatz, openly expressed her admiration for Brady. However, despite the initial buzz, there might be more to this story.
Quick recap: Tom Brady and Gisele Bündchen's separation last October marked the end of a 13-year marriage between the power couple. With the divorce came various rumors and speculations, particularly about who Brady might date next. Gisele Bündchen herself was seen spending time with her jiu-jitsu coach, Joaquim Valente, during a vacation in Costa Rica, but Tom Brady remained relatively distant from public romantic involvements.
During that time, Kendra made headlines when she candidly shared her admiration for Tom Brady with the New York Post.
“Obviously, he’s very physically attractive, but his work ethic is awesome — I love it,” said Middleton, “Like, he’s so dedicated to his craft that he doesn’t even eat tomatoes, you know what I mean?”
Despite growing up as a Jacksonville Jaguars fan, Middleton revealed that Tom Brady had always been her first football crush and assumed that the NFL player would quickly move on to another high-profile relationship, considering his status as a sports legend.
After that, the internet ran with it and declared Kendra Middleton as Tom Brady's latest fling!
After Tom and Gisele's divorce, rumors began to swirl. According to the New York Post, several women, including Playboy model Sara Blake, Brazilian model Mayara Lopes, and science researcher Bobbi Stark, were said to be interested in the quarterback. All these speculations have captured the public's attention, especially Tampa Bay and New England fans.
He and Gisele Bündchen have made it clear that their children, Benjamin and Vivian, remain their top priority, even after their separation.
After all the articles and tweets (some of them not-so-nice), Kendra took to social media to clarify the dating rumors and unequivocally stated that she is not dating Tom Brady, putting an end to the speculation. It appears that the initial reports of a budding romance were unfounded, and Brady may not even know the young journalist personally.
While the rumor mill continues to swirl around Tom Brady's dating life post-divorce, it's essential to separate fact from fiction. Kendra's admiration for the NFL superstar may have sparked the initial speculation, but her recent statement on social media confirms that she is not romantically involved with Brady. That being said, it's still a pretty funny and interesting story for Kendra.
TOM BRADY'S ROMANTIC HISTORY:
Layla Roberts

404221 14: Playboy model Layla Roberts signs autographs outside The Lounge club April 18, 2002 in West Hollywood, CA. (Photo by David Klein/Getty Images)
In 2002, Brady had a short-lived romance with the former Playboy model Layla Roberts, as reported by Us Weekly. During the same period, there were rumors of her involvement with Vin Diesel, but she later married AltaVista founder John Hilinski in 2004
Tara Reid

NEW YORK - JANUARY 25: Actress Tara Reid watches the game between the New York Knicks and the Phoenix Suns on January 25, 2005 at Madison Square Garden in New York City. NOTE TO USER: User expressly acknowledges and agrees that, by downloading and/or using this Photograph, user is consenting to the terms and conditions of the Getty Images License Agreement. (Photo by Jim McIsaac/Getty Images)
There were rumors that the quarterback had a fling with actress Tara Reid in 2002. In a 2014 interview with the Australian radio show "Kylie and Jackie O," Reid mentioned their kissing experience, noting that he was "pretty good-looking."
Bridget Moynahan

NEW YORK - MAY 01: Actress Bridget Moynahan and football player Tom Brady of the New England Patriots attend the Metropolitan Museum of Art Costume Institute Benefit Gala: Anglomania at the Metropolitan Museum of Art May 1, 2006 in New York City. (Photo by Peter Kramer/Getty Images)
Brady and the actor dated for three years but broke up in December 2006 when he started a relationship with Gisele Bündchen. After their split, Moynahan announced her pregnancy, giving birth to their son in August 2007.
Meghan Vasconcellos
There are reports suggesting that Brady had a brief involvement with a New England Patriots cheerleader in 2006 while he was still dating Moynahan. Subsequently, the cheerleader, Vasconcellos, found love with Brady's teammate, Lonie Paxton, and the couple tied the knot in 2011.
Gisele Bündchen
Veronika Rajek
Rumored earlier this year. However, she’s moved on to obsessing over Bengals Joe Burrow.
Irina Shayk

VERONA, ITALY - SEPTEMBER 20: Irina Shayk attends Intimissimi on Ice - OperaPop at the Arena di Verona on September 20, 2014 in Verona, Italy. The world diverted their eyes away from the catwalks of Milan to the Arena di Verona, where Intimissimi showed off their latest styles to the press and public on the spectacular frozen over amphitheatre. (Photo by Andreas Rentz/Getty Images for Intimissimi)
After parting ways with Bündchen, Brady appeared to have started a relationship with Shayk. They were photographed together in a cozy embrace during a weekend rendezvous, and Shayk reportedly spent the night at Brady's Los Angeles home. However, their romance was relatively short-lived, as it was reported their breakup in October, without disclosing further details.