Bucs owner Malcolm Glazer had the vision to trade for the young head coach with the visor and they made history in their first season by winning Super Bowl XXXVII.
Gruden still remembers the hot line to Raiders owner Al Davis ringing at his home in the middle of the night. The Bucs sent two first round picks, two second round picks and $8-million to Oakland in exchange for Gruden.
"It didn't put any pressure on me now,'' Gruden said. "Warren Sapp told me if you don't deliver a Super Bowl, we will kill you.
"You don't realize the compensation until the draft comes around. You miss the first and second round draft choices. And you really wish in hindsight we didn't have to give up anything. But it really made me work hard. It really gave me incentive to do the very best that I could for Mr. Glazer and the family that made that trade. And it was a lot to live up to. Maybe I never did but I'm not dead yet.''
Glazer and Gruden will be inducted into the team's Ring of Honor this season, 15 years after their greatest triumph in the Super Bowl against those same Raiders.
Glazer, who had been in declining health for a number of years after suffering two strokes, died in 2014 at age 85. He will be honored posthumously during a nationally televised Thursday night game Oct. 5 against the Patriots.
Gruden, 53, who served as the team's head coach from 2002-08 (going 57-55), will be inducted during halftime of the Bucs' Monday Night Football game that he will broadcast for ESPN on Dec. 18 against the Falcons.
"Jon Gruden is the reason I'm wearing this ring,'' said Bucs co-chairman Brian Glazer Wednesday. "He's also the reason my father was standing beside him holding the Lombardi Trophy and delivered on his promise to make the Buccaneers winners on and off the field.''
Wearing a red Bucs polo shirt and pulling the patented visor over his blonde hair, Gruden became emotional talking about his six seasons with the Bucs, reaching the playoffs in 2002, '05 and '07.
"I'm overwhelmed. I've very appreciative and humbled by this honor,'' Gruden said. "(Malcolm Glazer) had a vision, he had the guts, he had the courage to make this purchase and change the destiny of this franchise.
"When he called me in the middle of the night and made me a part of the organization, it was like a storybook opportunity for me to go home. … I'm a little choked up as you can see.''