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49ers repeating old mistakes: Will George Kittle stay or leave in a shocking contract drama?

The San Francisco 49ers are apparently in yet another tense contract negotiation stand-off with a star player — and this time, it’s with fan favorite George Kittle. 
 The 49ers appear to be fumbling George Kittle's contract

Kittle has remained one of the best tight ends in the NFL and is about to enter the final year of his five-year, $75 million extension he signed in 2020. It’s been clear for months that the Niners would need to extend him, but multiple insiders covering the 49ers say that any deal seems far away.

On Monday, the Athletic’s Mike Silver noted that the tight end is “a longshot” to report to the team’s voluntary offseason workouts, which begin on Tuesday. According to Silver, the two sides “remain far apart in discussions about a new deal.”

Silver’s report is in line with comments made by NBC Sports Bay Area’s 49ers reporter Matt Maiocco, who said the team is already behind in negotiations with Kittle.

“They’ve already, you know, done themselves a bit of a disservice with … the handling of George Kittle’s new deal,” said Maiocco on KNBR’s “Dirty Work” afternoon show on Friday.

As Maiocco explained, the Arizona Cardinals made their star tight end Trey McBride the highest paid tight end in NFL history when they awarded him a 4-year, $76 million extension earlier this month. His $19 million per year average took the top spot from Travis Kelce’s $17.125 million. In Maiocco’s eyes, the 49ers missed a window to get Kittle signed for cheaper.

“I would think if Trey McBride is making $19 million, shouldn’t George be making $20 million?” asked Maiocco. 

The 49ers have made waiting through the summer to ink their extensions a trend in the John Lynch/Kyle Shanahan era. Starting with Kittle in 2020, the Niners would not finalize their extensions until the start of training camp but managed to get them done around that time, including with Fred Warner in 2021 and Deebo Samuel in 2022.

But then the Nick Bosa negotiation in 2023 didn’t get resolved until just before the start of the regular season. And last year, both the Brandon Aiyuk and Trent Williams deals took until after training camp ended. All three didn’t practice with the team until after they signed their deals.

This offseason has been dominated mostly by chatter about Brock Purdy’s extension, which also isn’t resolved despite the quarterback saying he wanted it done already. Silver reported that there has been “some progress” and that Purdy is likely to get more than $50 million, but uncertainty about whether Purdy shows up on Tuesday remains. 

In Maiocco’s eyes, the 49ers have not been quick enough to try to get their stars signed, pointing to the reigning Super Bowl champs as a team that knows what it’s doing when it comes to contracts. 

“The Eagles are very proactive. They get their deals done,” Maiocco said. “The Cowboys, they don’t, and it costs them. And I think for the 49ers, that’s one area where I think that they could be the ones that set the market, rather than being the ones that have to respond to the market and then end up paying more.”

It’s never a good sign when you’re being compared to the Cowboys in terms of contract negotiations.

Kittle, for one, doesn’t seem to be too worried about the contract situation. The star tight end was recently seen downing a beer in one gulp at Wrestlemania 41.