Bill Simmons: “WHY NOW?? It’s been 20 years! You have a chance to have one of the all-time careers: drafted by a team and finishes your career with the team. Didn’t you watch the reaction with Kobe in Los Angeles and how much he meant to people here because he stayed here the whole time? Like what is better than that for a legacy? You’re going to go to Tampa, play for Bruce Arians, and have a bunch of 75-year-olds in the stands on a team with no history? How do you do this?? How is this how your career ends? I just don’t get it… I think he’s just going to keep going until this thing ends badly, and he has that same season that Peyton Manning had when Manning had 9 TDs and 17 INTs and people were wondering if Brock Osweiler should take his job. Is that how Brady wants this to end? I guess it is.” (Full Segment Above, Entire Interview Below)

Listen to Bill Simmons explain to Colin Cowherd why he thinks Tom Brady made a terrible mistake leaving New England after 20 years to sign on with a Tampa Bay Buccaneers team who hasn’t made the playoffs in 13 years.

Simmons says Brady was putting together one of the most legendary legacies in sports history considering he had won six Super Bowls with one franchise, and was going to start AND end his career with that same team as well, a feat extremely rare this day in age with salary caps and impatient executives fighting for their jobs.

Check out the audio above as Simmons details to Colin why Brady is heading towards ending his career the same way Peyton Manning did in Denver, as Manning’s final season in the NFL ended with him putting up one of the worst statistical seasons in league history and literally being forced to retire.

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