2025 NFL free agency Day 1 winners and losers: Mike Vrabel and Patriots get busy, 49ers clean house with mass exodus

The 2025 NFL free agency unofficially kicked off on Monday, with the legal tampering period, and some teams got busy with the annual spending frenzy. While this is only the negotiating window, with the official free agency beginning on Wednesday, several players have already agreed to new deals.

Here, we take a look at the winners and losers from Day 1 of the free agency period.

3 winners from Day 1 of 2025 NFL free agency

Chicago Bears QB Caleb Williams - Source: Getty

Chicago Bears

The Bears made the most of Day 1 of the tampering window by boosting their offensive and defensive lines. They agreed a deal with offensive lineman Drew Dalman to add protection to quarterback Caleb Williams.

Chicago also agreed deals with defensive tackle Grady Jarrett and defensive end Dayo Odeyingbo, ending the day on a high.

New England Patriots

Patriots coach Mike Vrabel saw his team spend big on Monday. New England's biggest acquisition was defensive tackle Milton Williams, who inked a four-year, $104 million contract.

The Patriots added further defensive cover in cornerback Carlton Davis III, linebackers Harold Landry and Robert Spillane and defensive tackle Khyiris Tonga. New England also agreed new deals with offensive tackle Morgan Moses and backup quarterback Joshua Dobbs.

Tampa Bay Buccaneers

The Buccaneers ensured that they still kept hold of some key players that will benefit the team next season. They offered new deals for wideout Chris Godwin, guard Ben Bredesen, and veteran linebacker Lavonte David.

Meanwhile, Tampa Bay let go of center Robert Hainsey. While there's still work to be done for the Buccaneers in the offseason, they got off to a good start.

3 losers from Day 1 of 2025 NFL free agency

NFL: San Francisco 49ers HC Kyle Shanahan - Source: Imagn

San Francisco 49ers

The 49ers dealt Deebo Samuel to the Washington Commanders at the beginning of the month, and Monday saw a mass exodus in full effect. The team also announced that Dre Greenlaw, Charvarius Ward, and Aaron Banks had agreed to terms with new teams while Javon Hargrave was being released.

Later in the day, San Francisco also decided to cut fullback Kyle Juszczyk. It will be interesting to see how the 49ers rebuild their squad in the offseason.

Dallas Cowboys

Despite the need to address some big issues this offseason, the Cowboys had a relatively quiet Day 1 of the free agency. Dallas did re-sign long snapper Trent Sieg to a three-year contract worth $4.45 million but there is still a lot of work to be done.

The Cowboys have a reported $52.7 million in cap space and should have been better prepared to agree deals with a few more players starting from Monday. Dallas is also reportedly planning an extension for Micah Parsons.

Jacksonville Jaguars

The Jaguars made a few questionable decisions on Monday. They released Evan Engram, but replaced him by signing two tight ends in Hunter Long and Johnny Mundt.

Jacksonville also offered extensions to some veteran players, including OT Chuma Edoga on a two-year deal and veteran lineman Patrick Mekari to a three-year contract worth $37.5 million. The Jaguars also gave wideout Dyami Brown a one-year agreement worth up to $12 million after his struggles in the 2024 season.