Much of the heavy lifting has already taken place this offseason for the Buccaneers. The team managed to retain both quarterback Baker Mayfield and receiver Mike Evans on multi-year deals and in doing so clear the way for safety Antoine Winfield Jr. to receive the franchise tag. 
The latter is currently set to earn $17.12MM in 2024, but that would only be the case if team and player were not able to hammer out a long-term agreement. Such a pact will carry a much higher price tag, of course, given Winfield’s age (25) and All-Pro status. A report from last month indicated the Buccaneers are optimistic a pact putting him atop the safety market will be worked out, and general manager Jason Licht recently confirmed that sentiment.
During an appearance on the Pat McAfee Show, Licht said there has been “positive movement” with respect to Winfield extension talks (video link via JC Allen of Bucs Gameday). Plenty of time remains before the mid-July deadline for tagged players to sign long-term deals. If no pact can be worked out before then, Winfield would enter the 2024 campaign as a pending free agent.
The two-time Pro Bowler’s tag ranks him third in the league amongst safeties with respect to annual average compensation. Only Derwin James ($19MM) and Minkah Fitzpatrick ($18.25MM) are higher in the pecking order, and Xavier McKinney‘s Packers contract is the lone one signed this offseason which comes close in terms of value. 2024 has seen the safety position devalued, leaving plenty of notable veterans unsigned well after the draft.
Nevertheless, Tampa Bay would be investing in Winfield’s prime years on a multi-year agreement. Working out a lucrative pact would keep a foundational defensive contributor in the fold for years to come, something which will be the case on the other side of the ball if a monster extension with left tackle Tristan Wirfs is worked out. Licht is also confident on that front.
As the Buccaneers seek a fourth straight NFC South title in 2024, Mayfield, Evans and fellow re-signee Lavonte David will all have crucial roles to play. The same will of course be true of Winfield, especially if he has a market-resetting deal in hand by the time the campaign begins. If Licht’s optimism is well placed, an agreement could be hammered out relatively soon.