Buffalo drafted Milano in the fifth round in 2017 out of Boston College, where the former safety had converted to linebacker as a sophomore. He thrived within the Bills' defense, carving a firm role as the team's best coverage linebacker.
He will be a free agent this offseason, however, and although re-signing him would be a no-brainer for the Bills in most offseasons -- this is not most offseasons.
The NFL's salary cap for the 2021 season, once believed to reach as high as $215 million, is now expected to drop to about $180 million according to ESPN's Adam Schefter. That's a tough break for the Bills, who will need to clear significant space in order to afford Milano and fellow free agent Jon Feliciano, a guard.
Per Spotrac, Milano's market value is $13.8 million per year. While it's unclear whether the Bills are willing to pay that figure, the team is absolutely willing to let him chase it.
"We'd love to be able to get Matt back. He knows that," Bills general manager Brandon Beane said. "I shared that with him and I'm sure [coach] Sean [McDermott] has as well. The business side matters. He's earned the right to go to free agency and see what his market bears."
The Bills place a high premium on drafting, developing and re-signing their own players. Although there hasn't been much opportunity to do so, as Beane is four years into his tenure with the franchise, Milano's draft classmates Tre'Davious White and Dion Dawkins received extensions last season.
Milano played the 2020 season without the long-term security of a contract extension and finished with a career-high 3.5 sacks despite playing in 10 games after dealing with various injuries. He has six sacks, five interceptions (one he returned for a TD as a rookie) and 21 passes defensed in his career, and he totaled 101 tackles in 2019.
But he also missed three games in 2018 with a broken leg and has played 16 games once in four pro seasons.
"His biggest thing is playing 16 games," Beane said. "That will be the first thing he'll tell you. He had some nicks here and there. It's just finding that balance."
Buffalo's defense was noticeably improved with Milano on the field and he was a key factor in its defensive turnaround over the past five games of the season, when the Bills ranked in the top 10 in yards allowed per game (307.2), rushing yards allowed per game (97.6) and passing yards allowed per game (209.6).
Arguably his best regular-season performance came against the New England Patriots in Week 16, when he had 8 tackles and a sack.
"No one's surprised by what Milano was able to do. That boy's a beast," Bills safety Micah Hyde said after the game. "He's sideline to sideline. Can cover. Had two huge third-down stops, really good tackles on some really good players. I think [one] was [Patriots running back James] White in the flat.
"That's what Milano is able to do for our defense, and when he's making plays like that, we're going to for sure be a lot better."
How difficult it will be for the Bills to bring Milano back depends on the salary cap. If it creeps past $180 million, Buffalo has several more options, including applying the roughly $15 million franchise tag and buying more time to negotiate a long-term deal.
"We'll do our best to retain him and as many guys as we can," Beane said. "There's going to be some tough decisions, unfortunately, for us. Whether it's letting guys go on this roster or having to watch guys leave [in free agency]."