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Bills Stuck with Tough Financial Decision on Former All-Pro Defender

Buffalo enters the offseason ranked fourth-best in dead cap across the NFL
Khari Demos|
Buffalo Bills' linebacker Matt Milano (58).
Buffalo Bills' linebacker Matt Milano (58). | Brian Fluharty-Imagn Images

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The Buffalo Bills have a lot of tough decisions to make this offseason. One will be deciding to keep a mainstay defender who has had ups and downs with injuries in recent years.

Matt Milano headlines a group of Bills' players whose void year deadlines came up on Monday. Milano, whose dead cap price tag is at $11.07 million, is also joined by fellow free agents Joey Bosa, Connor McGovern, DaQuan Jones, and A.J. Epenesa with the February 16 void deadline.

RELATED: Bills Can Create Significant Salary Cap Space Cutting $24 million Free-Agent Miss

Essentially, these players' 2026 cap hits could have a larger effect if they do not re-sign extensions in Buffalo. But Milano's price is most intriguing, as no other Bills' free agents carry a figure over $10 million.

Milano tops list

Of all the names on the list, Milano's may be the most consequential. Not only does he carry the highest cap hit, he is a polarizing figure for Bills Mafia.

After a 2022 first-team All-Pro selection, Milano's 2023, 2024 and 2025 seasons were marred by injuries. Those injuries directly affected his play, too. After three consecutive seasons with PFF grades of 70 or higher, from 2021 to 2023, the Boston College product has posted grades of 48.0 and 43.7 in 2024 and 2025, respectively.

In addition to the low grades, Milano has struggled to stay healthy and available in recent seasons.

MORE: 3 Bills' free-agent role players who deserve another contract

So, an extension does not seem likely. But especially for a deal in the range of over $11 million per year.

Matt Milano and RJ Harvey
Buffalo Bills' linebacker Matt Milano (58) and Denver Broncos' running back RJ Harvey (12). | Tina MacIntyre-Yee/Democrat and Chronicle / USA TODAY NETWORK via Imagn Images

The Buffalo fanbase seems to have come to terms with the fact that Milano will most likely not be with the Bills in 2026 and beyond. But what may now be a parting gift from the former fifth-round pick, Buffalo may have to deal with more than just replacing Milano on the field in 2026.

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Khari Demos
KHARI DEMOS

Khari Demos is an award-winning sports media creator and is a contributor for Bills On SI. He has written sports betting article covering the NFL for The Athletic and has written pieces about the NBA, MLB, college football and basketball, and more, throughout his career.