How Milano stayed in Buffalo

An exclusive inside look at how the negotiations went between the Bills and linebacker Matt Milano

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.

“Matt’s the consummate pro,” Segal said. “When we had our conversations, I let him know the Bills had a clear plan to re-sign him, but it was going have to be on hold because of the unique circumstances. He said, ‘Let’s go! I’m going to play great football, and the contract will take care of itself.'"

One day at a time turns into a season gone by pretty quickly, and by the time the Bills’ 2020 campaign was over, it was close to the end of January and free agency was just seven weeks away.

Beane said they never try to set a “hard deadline” in these situations, but, of course, he had to start getting some clarity so he could plan his team’s offseason, and even possible replacements for Milano if he knew they weren’t going to be able to retain him.

“That’s pretty much when it came to, 'Hey, we need to know now if he’s going to test free agency,'" Beane said. “So that if he was going to test, or maybe even sign somewhere else, we didn’t lose out on other players.”

Beane said the Bills had backup plans ready just in case Milano did want to test free agency and ultimately sign elsewhere.

“We had other deals that were coming into play, too, and they all affected each other," he said. "We can’t sign everyone. That was part of it. Not only [possibly] replacing Matt, but we can’t allot too much to too many guys.”

While Beane and his staff were making sure they had their contingency plans ready, Milano was also re-affirming his position to his agent. He wanted keep wearing a Bills uniform.

“When we were on the precipice of free agency, Matt called me and said, "Hey, go get a deal with the Bills. Get it done. I want to stay here,’” Segal explained. “We talked with Matt, talked to his family, and went over it together. We understood a baseline number we needed to stay, and then I went to go try to get a deal on his request.”

But the window for making that deal was closing fast, especially since he wasn’t the only pending free agent Beane wanted to keep. Guard Jon Feliciano and tackle Daryl Williams were also set to become unrestricted free agents.

Beane told Segal the team was going to give an offer, understanding the agent and his client would think about it and get back to him.

“There always needs to be a little bit of give-and-take on each side,” Beane said. “What’s important to Matt. What’s important to us, whether it’s the structure or the bonus, however it is.”

He trusted Segal, and Segal trusted him. It's a relationship between the two that dates back to when Beane was in Carolina, working his way up from a communications intern to the personnel department, eventually to Director of Football Operations and then assistant general manager.

Whether in Carolina or in Buffalo, Segal said Beane hasn’t changed, and appreciates his approach.

“He’s just remained consistent, professional, tough as they come, but willing to listen and hear out your points and your analysis, and then make a determination in what he believes is both fair and best for the club,” he said of the Bills general manager.

Segal represented numerous Panthers players while Beane was in Charlotte, but has also dealt with the Bills organization for many years before Beane ever arrived. He has the same high-level of respect for long-time contract negotiator Jim Overdorf, who was recently promoted from Senior Vice President of Football Administration to Senior Advisor to the General Manager and Football Operations.

Overdorf has worked for the Bills since 1986. He’s one of the longest tenured employees of any team in the National Football League.

“It’s part of the culture of the way they do things,” Segal said of working with the Bills. “Jim has been a guy I’ve worked with for 20 years, and I can say he’s honest, he is very, very protective of the club, and he’s going to make sure there’s a fair negotiation that considers both sides.”

The veteran agent is no stranger to all types of NFL deals, from first to late round picks. He’s negotiated record-setting contracts for Chicago Bears defensive end and University at Buffalo product Khalil Mack, as well as Panthers running back Christian McCaffrey, who Carolina chose eighth overall in 2017, just before Beane was hired by the Bills.

The George Washington University and Hofstra Law School graduate has been named one of the “100 Most Important NFL People” by USA TODAY and one of the “World's Most Powerful Sports Agents” by both Forbes Magazine and Sports Business Journal.

“He’s one of the best,” Beane said of Segal.  “He’s very transparent.  He doesn’t play a lot of games.  I just find him to be fair, truthful, and honest.  He fights hard for his clients, but I always find him to be fair in his reasoning.”

In addition to current Bills players Dawkins and Milano, Segal also represents defensive tackle Ed Oliver, who was the team’s first round pick in 2019. Oliver has two years remaining on his rookie contract.

But while all of the compliments going back-and-forth certainly create a healthy dynamic that allows deals to get done between the two, they, of course, don’t always work out. That’s been the case with other players Segal has represented while Beane has been the general manager of the Bills. Players like defensive tackle Jordan Phillips, who had a career year in Buffalo in 2019, left as a free agent to sign a three-year, $30 million contract with the Arizona Cardinals prior to the 2020 season.

"There are plenty of times we’ve dealt together and said, 'There’s no deal here. It doesn’t work for you or it doesn’t work for me,’" said Beane of those negotiations where it doesn't worked out. "But the great thing is no harm, no foul. We respect each other’s position.”

That could have been the case with Milano, but both sides knew there was a willingness to get a deal done, and were working to make it happen.

The new league year and free agency was set to begin on March 17, but teams were allowed to begin contacting agents like Segal about their pending free agent clients starting on March 15. Most analysts had the 26-year-old ranked as the No. 2 non-edge rushing linebacker set to hit the open market, behind only the Tampa Bay Buccaneers linebacker Lavonte David.

The 31-year old David ended up signing a two-year, $25 million contract extension with the Buccaneers on Friday, March 12, with $20 million guaranteed. An average of $12.5 million for those two years. Did that cause either Beane or Segal to adjust their thinking on Milano? Did David’s deal set a bar, or even a comparison, for what Milano would be getting?

Although that can happen in some situations, both men said it had no impact here.

“We had our value, we knew what it was,” Beane said of Milano. “On our end, that never came up.”

“We had done a lot of preparation,” Segal said. “Based upon the value to the club, analytics, Matt’s feelings of where he wants to be, what he wants to do, and absolutely have a price in mind that is unique to our situation,” adding that they were always “totally laser-focused” on Milano’s situation.

Segal declined to say exactly what goes into all of their analytics for each client, but on March 11, just after 4 p.m. ET, six days before free agency was set to begin and four days before he would have been allowed to negotiate with other clubs, all of that preparation, focus, and communication came together for the outcome each side had been working towards for over a year. Milano agreed to a new four-year contract.

While neither the Bills nor Segal disclosed any of the financial details, sources told WGR, at the time of signing, the new contract can pay Milano up to $44 million, and includes $24 million guaranteed.

It was a deal that worked for both sides.

“They had to make sure it was something they were happy with, excited about, and we needed to make sure it was something we thought was a good deal for us, and those are the best deals,” Beane said.

“To re-sign a guy that started his career here, it backs up what we preach around here, which is draft, develop, and sign your own. This was an exciting one. It was cool. Until it was agreed upon, I didn’t have a feeling either way. I thought it could go either way. At the end of the day, we were excited that we’re going have Matt here for the foreseeable future. He’s done great things and we think he will continue to.”

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Featured Image Photo Credit: Jamie Germano - Rochester Democrat and Chronicle via USA TODAY Sports