Jawaan Taylor carried considerable value as a 2023 free agent. Ranked third on PFR’s FA list heading into that league year, the four-season Jaguars right tackle starter fetched a player-friendly contract from a Chiefs team that paid up to replace Andrew Wylie.

The Chiefs gave Taylor a four-year, $80MM deal — one that brought an important date in March 2024. A rolling guarantee structure meant that if Taylor was on Kansas City’s roster by mid-March of last year, his 2025 base salary would become fully guaranteed. The Chiefs did not see Taylor justify the cost in 2023, but they were in no position to cut or trade him after one season. As a result, they are on the hook for his $19.5MM salary this year.

Tackle issues hounded the Chiefs last season. Their tightrope walk to Super Bowl LIX featured four LT starters, as the team’s post-Orlando Brown Jr. setup there received more attention. Taylor has remained mostly healthy, and the former second-round pick made 19 starts for the AFC champions last season. Of course, Taylor has not played especially well in K.C. His 14 penalties last season ranked second in the NFL; that showing came after a 2023 season that featured Taylor being whistled for five more infractions (17) than anyone else that year.

Kansas City’s undoing in Super Bowl LIX brought worse optics compared to the team’s blowout loss in Super Bowl LV, as the latter matchup involved backup options at both tackle positions. The Chiefs had no injury issues up front against the Eagles, but their line endured an onslaught against a defense that did not blitz in the game. As a result of this rout, the Chiefs invested heavily at tackle by giving Jaylon Moore a two-year deal worth $30MM and then drafting Josh Simmons in Round 1. These moves may end up affecting Taylor.

Despite the lofty salary guarantee, Taylor could lose his starting RT job. The seventh-year blocker should not be considered a lock to retain it, per The Athletic’s Michael Silver. A scenario in which Simmons commandeers the Chiefs’ starting LT post and Moore earns the RT gig is in play. That would stand to provide an upgrade for the Chiefs, though both imports come with questions. Simmons fell to No. 31 because of a patellar tendon tear and character issues, while Moore did not grade well in limited duty in San Francisco. But Taylor’s struggles, which have also involved scrutiny on his alignment and phantom false starts, may point the Chiefs to preferring Moore take over at RT immediately — rather than after a cap casualty-based Taylor release in 2026.

The Chiefs also traded their most accomplished O-lineman, Joe Thuney, to the Bears for a 2026 fourth-round pick. They are giving 2024 second-round pick Kingsley Suamataia, whom Andy Reid quickly benched after he had won the job over Wanya Morris during training camp, an opportunity to replace Thuney at left guard.

Although Thuney drew a tough assignment by switching to tackle as the team’s emergency solution amid a string of failed options, he earned first-team All-Pro acclaim in 2022 and ’23. The Chiefs will need to brace for a significant step back at guard, though they will obviously hope improvement at tackle will help offset this.

The player who filled in for Thuney after his in-season move to LT, Mike Caliendo, is also competing for the left guard spot, Silver adds. A 2022 UDFA, Caliendo made six starts at guard last season and played in 17 games as a Chiefs backup in 2023. Suamataia did play 31 snaps at guard following his tackle demotion, but the former BYU tackle standout being given such a quick hook at his primary position and being asked to replace an All-Pro will be an interesting dynamic to follow as the Chiefs attempt to join only the early-1990s Bills as teams to book four straight Super Bowl berths.