Here me out.
I want to see the Bucs tear it up in the playoffs. Not for immediate gratification but long term success of the team. Winston is probably the biggest draw for this team. The dude is only 22 and if he continues to show improvement plus keep winning, free agents will come.
Besides money, going to a successful and stable franchise is a big deal for free agents. At least that's what I believe. Free agents can look at the Bucs with Winston and see the potential for a strong playoff/Super Bowl contender for a decade plus.
Winston continues do well means that Koetter will remain head coach for a while. Continuity at the head coach position is also pretty big.
Winston already is a strong personality that players gravitate to. The added bit of a bright future ahead for this team starts to become tempting. It's also big for keeping your own players that you deem worthy to stay.
Every team has that Franchise defining moment that either vaults you into prominence or drops you back down to dwell in the basement.
