The San Francisco 49ers are no strangers to tense contract negotiations. The organization operates on its own terms, often allowing talks to extend late into the preseason. However, this strategy typically works in their favor. Under general manager John Lynch, the front office has a strong track record of compensating their star players appropriately. That said, negotiations can sometimes stall, leading to trade discussions or prolonged holdouts—just ask Deebo Samuel.
After an All-Pro season in 2021, Samuel understandably sought a new contract. While the 49ers were open to an extension, the process was drawn out, resulting in a public trade request and a training camp holdout. Now, in the final year of his three-year, $71 million contract, Samuel wants out. Following his exit interview in January, he formally requested a trade, signaling the end of his tenure in San Francisco. Though he remains one of the franchise’s most dynamic and beloved players, his contract was the first major deal the 49ers seemingly came to regret.
Despite previous missteps with contracts—such as those of Jerick McKinnon, Dee Ford, and Javon Hargrave—Samuel’s situation left San Francisco’s leadership particularly frustrated. Surprisingly, that sentiment also applies to two of their highest-paid players.
49ers Frustrated with Brandon Aiyuk?
On August 30, 2024, the 49ers and wide receiver Brandon Aiyuk reached an agreement on a four-year, $120 million extension. The deal concluded a long, contentious negotiation period that involved a trade request, controversial podcast appearances, social media drama, and a hold-in during training camp.
According to Tim Kawakami of the San Francisco Standard, the 49ers still harbor frustration over how Aiyuk handled the situation.
“There is still lingering resentment over Aiyuk’s approach to negotiations last summer. Some members of the front office were never fully on board with giving him $30 million per year just before the regular season began.”
From a financial standpoint, Aiyuk’s contract could become one of the biggest uncertainties of the Kyle Shanahan era. After suffering a torn ACL in October, his future remains uncertain. Interestingly, his time with the 49ers nearly ended last offseason, as general manager John Lynch was engaged in trade discussions with the Pittsburgh Steelers. However, just before a deal was finalized, Shanahan intervened, informing Lynch that Aiyuk was prepared to sign.
Ironically, wide receivers have caused the 49ers the most stress in contract negotiations. However, Nick Bosa gave Aiyuk stiff competition in dragging out talks before the 2023 season.
49ers Resent Giving In to Nick Bosa
No team enjoys conceding in contract talks, and for the 49ers’ front office, signing Nick Bosa to a five-year, $170 million deal felt like a major loss, according to Kawakami.
“For a team that despises setting financial precedents, the 49ers likely regret caving and awarding Bosa $34 million per year and $120 million guaranteed—still the highest salary and most guaranteed money for a defensive player in the league—two Septembers ago after his lengthy holdout.”
While paying Bosa was the right decision, as he remains a cornerstone of their defense, San Francisco’s reluctance to reset the market raises questions about quarterback Brock Purdy’s future.
Reports suggest Purdy isn’t seeking a record-breaking contract. However, given the 49ers’ approach, even if he aimed to surpass Dak Prescott’s $60 million annual salary, the team would likely refuse.