How Milano stayed in Buffalo

An exclusive inside look at how the negotiations went between the Bills and linebacker Matt Milano
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One year ago, hardly anyone thought it could be done.

Coming off their second playoff appearance in three years, several key contracts on the horizon, and a pandemic that was about to cause the salary cap to decrease for the first time in a decade, very few people saw a path for the Buffalo Bills to be able to re-sign cornerback Tre’Davious White, left tackle Dion Dawkins, and linebacker Matt Milano.

All players from the 2017 NFL Draft class, the first under head coach Sean McDermott, and just before Brandon Beane arrived as general manager. All huge pieces to the team’s success immediately, helping the organization break a 17-year playoff drought their rookie year, and all continually proving to be vital parts of a championship caliber roster.

Dawkins was the first to receive his extension, a four-year, $58.3 million deal, locking up the team’s left tackle to protect quarterback Josh Allen. His deal was negotiated by Joel Segal, an NFL agent of 27 years, who also represents Milano.

The Bills were never in danger of losing White after the 2020 season, since the team had already exercised his fifth-year option, but Beane made sure he’d be around for a while, too, inking him to a four-year, $70 million extension, briefly making him the highest-paid cornerback in the league.

Two of the big three were now signed, sealed, and delivered for the next several years. One more to go.

Milano was a fifth round pick out of Boston College, who took over as the starting weakside linebacker in the final month of his rookie year and was coming off a 101-tackle season.

Beane certainly wanted to keep him, but the team just didn’t have enough salary cap room to do it prior to last season. There was still the uncertainty of how much space would be available this year without knowing how the NFL would adjust the salary cap.

The Bills general manager made it clear to Segal how important Milano was to the organization, and told both the agent and player that they wanted to get a deal done to retain him. The good news for the Bills was that Milano also told Segal, long considered one of the power-agents in the NFL, that he wanted to stay in Buffalo.

Even though both sides clearly knew they wanted to reach the same outcome, all of the common desire in the world doesn’t mean much unless the two parties have enough mutual respect for one another to allow the process to play out and keep the lines of communication open and honest.

That’s exactly what happened, and a big reason both Beane and Segal agreed to speak to WGR on the record for this story. Both men provided insight into Milano’s re-signing from their own perspectives, but also described a very honest and respectful agent-to-general manager relationship that helped make it happen.

“It was great open dialogue with Joel, and that’s the best way to come to a positive outcome,” Beane said of the negotiations. “The great thing was Matt said all along that he wanted to be here. Joel said all along that Matt wants to be here. But it had to be the right deal for him and his family, as well as the right deal for us and our cap situation.”

Segal echoed those sentiments.

“Going into the last year, we were cognizant of the fact that this was going to be big for Matt, knowing he’s [going to be] an unrestricted free agent,” he said. “The Bills were consistent in their efforts and desire to keep Matt in Buffalo, and very upfront with the fact that there’s only so much money available in the cap and that we would have to see what happens. So we really agreed to take it one day at a time.”

Segal kept his client aware of what was happening every step of the way. Although they both recognized the challenge, it also presented opportunity for Milano, who never panicked or wavered.