The Tampa Bay Buccaneers are currently sitting atop of the NFC South and have a solid chance of making the playoffs yet again.

If Baker Mayfield and company can make it to the postseason, it would mark the 5th-straight season Tampa Bay reached the playoffs. After a 12-year drought from 2008 to 2019, the Buccaneers signed Tom Brady in free agency after his dominant run with the Patriots where he won six Super Bowls and was the catalyst behind a dynasty.

Despite being 43-years-old, the Bucs brass felt like Brady had some game left in him and a chip on his shoulder to prove he could still play at a high level, and the move paid off big time. Brady led the Tampa Bay Buccaneers to a Super Bowl victory in his very first season as the team’s starting QB in 2020 and went on to be named MVP of the big game.

Brady returned in 2021 and led the Bucs to a (13-4) finish in the regular season, but they fell in the divisional round to the Philadelphia Eagles.

Finally, despite an up and down campaign in his final NFL season in 2022, Brady and the Bucs snuck into the postseason with an (8-9) record, but lost to the Dallas Cowboys in the wildcard round.

While the acquisition of Brady will always go down as one of the best moves in Buccaneers team history, there was a trade in the early 2000’s that is getting praised as one of the “biggest trades of the last quarter century.”

In February of 2002, the Bucs traded 1st-round pick, 2002 2nd-round pick, 2003 1st-round pick, 2004 2nd-round pick, and coughed up $8 million to the Raiders to secure Jon Gruden as their head coach.

Bleacher Report recently published a article titled the “25 Biggest Sports Trades of the Last Quarter Century” and ranked the Tampa Bay Buccaneers move for Gruden as 23rd on a list with some massive moves from the NFL, NBA and MLB since 2000:

“I felt that I put the price tag so high that they wouldn’t agree to it. And they did. Gruden is no longer our coach.”

That’s what legendary Oakland Raiders owner Al Davis told Pro Bowl tackle Lincoln Kennedy (via Paul Gutierrez of ESPN) after reports surfaced that head coach Jon Gruden had been traded to the Tampa Bay Buccaneers during the 2002 Pro Bowl.

After going 48-26 in four seasons with the Raiders while winning back-to-back AFC West titles, Gruden was a coaching star on the rise and still only 38 years old at the time of the trade.

He made an immediate splash in Tampa Bay, leading the Buccaneers to a 12-4 record and steamrolling the 49ers and Eagles en route to the Super Bowl, where he met up with none other than the Raiders team he had just left behind.

On the strength of one of the best defenses in NFL history, the Buccaneers rolled to a 48-21 victory, and Gruden became the youngest head coach ever to win a Super Bowl. That record has since been surpassed by Mike Tomlin and Sean McVay.

He spent six more seasons as the Buccaneers head coach, making just two other playoff appearances and losing in the first round both times, but his legacy in Tampa Bay was cemented with his Super Bowl win.”