George Kittle signed a five-year, $75 million extension with the San Francisco 49ers in 2020. Back then, the Niners found themselves in a much different spot, ready to spend and build on their contender to capitalize on a championship window. Those four years since have seen plenty of successes that Kittle has contributed to. Three conference championship game appearances and one Super Bowl appearance makes them one of the NFC’s better teams in that stretch.

But San Francisco has not gotten over the hump to end that drought. 2024, the fourth season since Kittle’s extension, went up in smoke with numerous key injuries. A drastic fall from grace forced the Niners to reevaluate their roster building strategy. This offseason, they let a number of free agents walk and traded star receiver Deebo Samuel to the Washington Commanders. General Manager John Lynch’s comments at the NFL Scouting Combine even suggested the team had interest in moving Samuel’s counterpart Brandon Aiyuk as well.

Altogether, that leaves the Niners searching for a fresh start and they will get younger and cheaper with the talent acquired during the NFL Draft. With that final year still to go on Kittle’s contract, where do both sides stand on the tight end’s future with the team? Kittle’s cap hit for 2025 will count over $22 million to the Niners’ cap. Last season, he showed no signs of slowing down after totaling 78 catches for 1,106 yards and eight touchdowns.

However, the Niners’ current direction casts doubt on their meeting Kittle’s asking price. The duality of those two factors is also enhanced with the lingering task of extending quarterback Brock Purdy. That was laid out as a prime objective heading into the offseason yet has no target for completion at this point. Until that gets done, it would seem that any other big picture moves come secondary.

The Niners and Kittle have had a positive working relationship over the years. But both sides face major questions when it comes to a potential extension. Kittle must want to remain in the Bay Area and the Niners must commit to a significant dollar amount to keep him.