The Steelers confront a familiar offseason crossroads: Cameron Heyward and Chris Boswell each carry two years left on what could be big-money deals, but Pittsburgh has a history of waiting until a final season to extend. Heyward has been a spectator at camp as talks swirl over tearing up the pact he signed last year, while Boswell has initiated a hold-in in pursuit of a raise with Boswell’s status amplified by rookie Ben Sauls filling in. The Steelers could choose to push for one deal and let both veterans roll into the season, or consider a path where one extension changes the team’s dynamic entering 2025. The choice isn’t just about cap space; it’s about leadership, reliability, and how each decision could ripple through roster construction and fantasy value. Fans are invited to weigh in via the poll on which extension would matter more for the club and for fantasy rosters in the upcoming season.

Two things to watch: Heyward’s impact as a veteran anchor on the defensive line and Boswell’s stability as a kicker who could shape scoring ceilings. Boswell’s hold-in could test the Steelers’ leverage, while Heyward’s durability and leadership could influence inside-pressure and run defense chemistry. The Sauls-in moment also provides a live look at how Pittsburgh plans to handle a potential Boswell absence in the event of stalled talks. In fantasy terms, the decision could tilt early-season field-goal workload and DL pressure opportunities, making this offseason decision one of the most consequential in Pittsburgh this year.