This one still stings even two years later.
When the Patriots signed Stephon Gilmore in 2017 after he spent five seasons with the Bills, the reactions to the news weren't all that positive, mainly because people took issue with his contract. He was given a five-year, $65 million contract, keeping him tied to New England through the 2021 season.
Although that may have seemed like an outrageous amount at the time, Gilmore proved it was the right move at the right time.
He was immediately put in as a starter, lining up across the field from Super Bowl XLIX hero Malcolm Butler and had a productive first season in Foxboro. He earned the reputation of being a fear-inducing player on the field with one of the most memorable moments in a championship game, snagging the game-saving pass breakup in the AFC Championship game against the Jaguars.
The 2018 season saw much of the same performance from him as the year before, ending the year with a bang as his well-timed interception in Super Bowl LIII against the Rams helped secure the sixth championship win for the franchise. His performance this season also earned him a second Pro Bowl selection and first-team All-Pro honors.
The following season, however, is what Gilmore will be most remembered for.
Besides leading the league with six interceptions and 20 passes defended, the cornerback's performance that season won earned him the Defensive Player of the Year award, the first Patriot to win the award in the franchise's history.
During the 2020 season, Gilmore had his usual reliable and impressive performance throughout the regular season until he suffered a season-ending injury in week 15. It was the last time he would take the field as a Patriot.
He began the 2021 season on the PUP list, and after conflicting reports regarding his contract status and Belichick's feelings about him, Gilmore was traded in early October to the Panthers for just a sixth-round draft pick.
He would have a decent half-season in Carolina and signed with the Colts the following year. He's continued to be a threat in any secondary he lines up in and could've been exactly what the Patriots needed had they figured out his contract situation to keep him in New England for as long as possible.