TAMPA, Fla. (WFLA) – The Buccaneers’ first playoff game is less than a week away, but will Monday night’s game be the last time quarterback Tom Brady plays at Raymond James?

On Jan. 16, the Tampa Bay Buccaneers will go head-to-head against the Dallas Cowboys for the second time this season, but this time there’s a lot more on the line. Whenever the Buccaneers’ season comes to an end, speculation about where the future Hall of Fame quarterback will end up is likely to begin.

Since joining the team in 2020, Brady has led the Bucs to a Super Bowl and two playoff berths, but once Tampa Bay’s postseason is done, will Brady be? The star quarterback is set to become an unrestricted free agent following the post season, leaving his future endeavors a mystery.

On last week’s episode of Bucs Bonus, WFLA Bucs Insiders Dan Lucas and Karen Loftus discussed Brady’s playing future and what route he could take.

“I think there’s a lot more to his decision than just do I want to keep playing football,” Lucas said. “Obviously he wants to be somewhere that’s competitive and has a chance to win a championship. The issue goes beyond Brady, as far as the Bucs are concerned, they have to deal with this salary cap thing head-on.”

“They’ve got some contracts coming up, some very uncomfortable conversations coming up with guys like Lavonte David. They’re gonna have to move some money around and I think that Tom Brady would like to have some assurance that things are either going to be status quo with his guys or even bigger things are going to be in play for him,” Lucas continued.

According to spotrac.com, the Buccaneers have 26 players that will become free agents once the postseason ends.

“There are so many facets to this and I think a lot of it may have to do with the fact, what if the Bucs win the Super Bowl this year?” Loftus added to the conversation. “If they win it all, does he tie a bow on his career for real this time and call it a career? I think it’s a hard thing to even project because, in my head, I’m thinking his decisions will be dependent on how this season finishes up and if he feels like there’s unfinished business,” Loftus continued.

After the Bucs’ regular season ended with a 30-17 loss to the Atlanta Falcons, the Bucs dipped below .500 heading into the playoffs. Brady also finished the season with a losing record for the first time in his NFL career.

“We know he has business ventures, we know he has the Fox Sports gig lined up whenever he’s ready to do it, but as he’s stated, as we’ve seen, he’s in terrific shape, still throwing the ball well, so why wouldn’t a team want him?” Lucas said.

“He’s not going somewhere unless he thinks he can win a Super Bowl and the rumors of the places that have him going – there’s some of those that I don’t see ready for a Super Bowl,” Lucas added.

As the Buccaneers focus on reaching the Super Bowl, the future of Brady and Tampa Bay remains unknown and will probably stay that way until his free agency opens up on March 15, 2023.