The Bucs paid a steep price for Gruden, but most fans would say that, considering what he delivered the franchise, it was well worth the price of admission.
With the NFL news cycle struggling to produce amid the coronavirus crisis, let's take a deep dive into this blockbuster to see who came out on top in the end.
Raiders-Buccaneers Jon Gruden Trade Details
Raiders acquire: two first-round picks, two second-round picks, and $8 million
Buccaneers acquire: Jon Gruden
Gruden would famously deliver on his promise and capture the Super Bowl XXXVII crown in a 48-21 over the ... Raiders. It marked the first world championship in Buccaneers history, but Tampa would struggle to maintain that level of success, making the playoffs just twice over the next six campaigns.
As for the Raiders, those picks would turn into No. 21 overall and No. 53 overall in 2002 and No. 32 overall and No. 33 overall in 2003. In a trade with Washington and Atlanta involving the No. 21 overall pick, Oakland landed the No. 17 overall pick in 2002 and drafted cornerback Phillip Buchanon.
With the No. 53 overall pick, the Raiders chose offensive tackle Langston Walker. The franchise would then make a series of other trades involving the No. 33 overall pick in 2003. In the end, Oakland landed defensive end Tyler Brayton, linebacker Sam Williams, and wide receiver Ryan Hoag in the 2003 draft.
Who Won the Trade?
The Raiders stockpiled a ton of draft capital with the picks they acquired in the Gruden trade. Though some players -- like Buchanon, Walker, and Brayton -- had decent careers, none of them blossomed into stars. In fact, Hoag never recorded a reception in his four NFL seasons and Williams never recorded more than 38 tackles in a single season.
Tampa Bay won this trade in that none of the four picks it unloaded proved to be all that valuable. More importantly, Gruden delivered the Bucs their first-ever Super Bowl title.