Ranking Top 4 Chiefs Free Agents by Importance of Re-Signing

KANSAS CITY, Mo. – Long snappers are the opposite of the jingle from Cheers. They’re most valued when nobody knows their names. In other words, when they don’t make mistakes snapping for punts and placekicks, they remain anonymous.

But James Winchester has three Super Bowl rings, more than any active NFL player at his position, so he’s well known across the league. He’s also now the highest-paid player at his position after he reportedly agreed to terms on a one-year, $1.75 million extension on Saturday. And he’s the most important impending free agent the Chiefs needed to re-sign.

Every point will matter in 2026 with Patrick Mahomes returning from ACL surgery and the Chiefs’ defense needing to rebuild its secondary. The chemistry Winchester has developed with kicker Harrison Butker and holder Matt Araiza is pivotal. The Chiefs can’t afford field-position shifts and missing points in the parity of the AFC West.

The team’s oldest player, two months older than Travis Kelce, Winchester turns 37 in August. He enters 2026 with the league’s fifth-longest current streak of consecutive games played at 181.

veac — Feb 24, 2026; Indianapolis, IN, USA; Kansas City Chiefs general manager Brett Veach speaks at the NFL Scouting Combine at the Indiana Convention Center. Mandatory Credit: Kirby Lee-Imagn Images | Kirby Lee-Imagn Images

J.J. Jansen (277), Jon Weeks (261), Johnny Hekker (229) and Jake Matthews (195) rank 1-4. Winchester’s streak is 206 including playoffs.

Here are the next three most important free agents the Chiefs need to re-sign.

Jaylen Watson

As the 243rd overall selection in 2022, Jaylen Watson made $6,051,368 total in combined salary and signing bonus over his first four NFL seasons. Unfortunately for Kansas City, he’ll become the top-ranked cornerback on the market when free agency kicks off at 11 a.m. CT on Monday.

Watson fired off another cryptic tweet on Saturday, an emoji of an hourglass. Perhaps it’s a signal to the Chiefs that time is running out on a counter-offer from his agent. After Kansas City traded Trent McDuffie to the Rams on Wednesday, the Chiefs need Watson more than ever.

coo — Oct 12, 2025; Kansas City, Missouri, USA; Kansas City Chiefs safety Bryan Cook (6) takes Detroit Lions wide receiver Jameson Williams (1) during the second half at GEHA Field at Arrowhead Stadium. Mandatory Credit: Jay Biggerstaff-Imagn Images | Jay Biggerstaff-Imagn Images

Bryan Cook

While Watson is expected to set the market for free-agent cornerbacks on Monday, Cook is expected to set the market for safeties. Re-signing Cook would be mammoth for the Chiefs because he’s the quarterback on the back end of Steve Spagnuolo’s defense. After Kansas City’s 31-28 loss at Dallas on Thanksgiving, Cook’s unexpected injury caused a series of dominoes that allowed the Cowboys to take command of the game at a crucial moment.

Tyquan Thornton

The Chiefs entered 2025 with an aggressive offensive mindset, looking to hit downfield throws much more often than the year prior. Through Week 11, Thornton was in the lead role of that endeavor. He woke up Nov. 17 leading the NFL with a 24.8-yard average per catch. And while he tapered off in the last half of the season, Thornton is pivotal because he’s proven he can connect with Mahomes on the deep ball, something that opens up the middle of the field.

Thornton also showed a unique ability to snatch passes out of the air, beating defenders to the high point, and those passes stuck in his hand like a bee on honey. He’s a must-have in 2026 for the Chiefs, who also are set to lose JuJu Smith-Schuster and Hollywood Brown in free agency, and potentially Rashee Rice to another suspension.