Tyreek Hill’s pursuit of an extension isn’t Miami Dolphins GM Chris Grier’s first time navigating a contract dispute

Last week, Pro Football Talk’s Mike Florio detailed Tyreek Hill’s decaying contract just hours before the Miami Dolphins signed Jaylen Waddle to a three-year contract extension… there was a disturbance in the force.

Hill, 30, signed a four-year contract extension with the Dolphins, including a $56 million cap number for 2026. Despite the high number, Miami can escape Hill’s contract after the 2025 season with $11 million in dead money while saving $45 million against the cap.

The Minnesota Vikings signed Justin Jefferson to a four-year $140 million contract extension on Monday — another major wide receiver deal in an offseason that saw Waddle, Amon-Ra St.Brown, and A.J. Brown all sign monster contracts. It’s easy to understand Hill’s request after 3,509 receiving yards and 21 touchdowns since arriving in South Florida.

The hope for an extension leaves Dolphins general manager Chris Grier in a tough spot. Miami needs to sign quarterback Tua Tagovailoa to a new contract, former first-round pick Jaelan Phillips is due for an extension, and safety Jevon Holland will become a free agent following the 2024 season. Have I mentioned that the Dolphins are $15 million over the 2025 salary cap?

It’s important to remember that Miami reached the playoffs in both seasons since signing Hill. Upsetting the five-time First-team All-Pro would be less than ideal while pushing for the franchise’s first playoff win in over 20 years.

Grier faces tough choices and must walk a fine line, but this isn’t the first time he’s managed disgruntled superstars. Miami faced a similar situation with cornerback Xavien Howard after signing former Dallas Cowboys defensive back Byron Jones to a five-year $82.5 million contract in 2020.

One key difference, however, is Howard wasn’t happy with the franchise. Hill continues to praise the franchise that traded two first-round picks for his services.

“I would like to retire in Miami, but we all know how the NFL is, how jobs go, and people getting promotions over here and — you know — we understand that,” Hill said on the Around the Bar Podcast. “But Miami is a great city, man. I love the team I play on, love the guys in the locker room, love the head coach, love the GM. So that means sign me. I love all you guys so much, I want to stay in Miami forever, man.

“Keep me there.”

Howard publicly asked for a trade and the Dolphins declined his request to move $4 million around. All that said, Miami and Howard still agreed on a re-structured contract that included $4.5 million in incentives before the 2021 season.

Not only that, the Dolphins and Howard settled remaining issues the following offseason, reaching a five-year deal that included the most guaranteed money for a cornerback at the time.

Hill’s league-leading 1,799 receiving yards were the seventh-most in a single season in NFL history and he’s caught 119 passes in both of the last two seasons. That must be worth a few more seasons as one of the league’s highest-paid wide receivers — right?

Only the Kansas City Chiefs and Buffalo Bills have more consecutive seasons than Miami with a winning record. Hill’s been critical to recent success and Grier’s track record follows what ESPN’s Adam Schefter mentioned Monday morning: The Dolphins will figure out a way to adjust Hill’s deal.