49ers’ contentious approach to contracts comes at a cost. Trent Williams knows

In 2024, four years removed from his first head-to-head tussle with the front office, Kittle broached the topic unprompted during an interview with the Chronicle for a story about the fear of being fired that fueled him, even during another 1,000-yard season. Where did that fear originate? After explaining in detail, Kittle then revealed how his 2020 negotiations also shaped his perspective. He saw “behind the curtain” and realized his employer could be ruthless: The 49ers had been cutthroat when it came to cash. “Anytime someone is telling you what they think your value is — specifically like when they lowball the hell out of you — it’s not a really fun feeling,” Kittle said. However, after the 49ers’ bitter 2024 negotiations with Aiyuk were their messiest yet, it appeared Lynch and chief negotiator Paraag Marathe had altered their approach last year. After years of all-offseason negotiations that lasted into training camp and sometimes beyond Labor Day, they finalized three massive extensions before Memorial Day, with Kittle (April 29), quarterback Brock Purdy (May 16) and linebacker Fred Warner (May 19). The 49ers want to lower Williams’ team-high salary cap number ($38.8 million) by signing him to an extension that would lessen the 2026 burden. And Lynch has acknowledged that Williams’ age is a complicating factor. That is, how much money should the 49ers guarantee Williams in 2027 when he’ll be in his age-39 season? Still, there appears to be a reasonable solution. The 49ers could comfortably carry Willliams’ salary on their 2026 books because they aren’t facing a salary cap crunch: Last week, they received a cap adjustment and restructured pass rusher Nick Bosa’s contract, transactions that gave them more than $38 million of additional space. They could have Williams play out his contract this season and use a high-end pick in the 2026 or 2027 draft to select his replacement. If that’s not a preferred course of action for one or both sides? It doesn’t appear extension talks should be overly complex. After all, the two parties agreed to Williams’ current contract just 18 months ago, when Williams was 36 and similar factors were at play. Williams said his age was a key discussion point before he signed a three-year, $82.6 million deal in September 2024. Perhaps their latest hardline negotiating will get Williams to lower his price. But it’s worth asking if their bruising approach has come at too high of a price in past seasons: Samuel and Bosa said their protracted negotiations impacted their performance in 2022 and 2023, respectively, and the 2024 standoff with soon-to-be-jettisoned Aiyuk created a rift that never fully healed. The potential fallout could be modest with Williams, a 15-year veteran who might be as savvy as Kittle was naïve in 2020, when he was entering his fourth season. Williams had already seen behind the curtain before this year’s contract talks with the 49ers. After signing his latest deal in 2024 after a 40-day holdout, he was said it was part of a “tough business” and he expected there to be blood.