The 49ers find themselves in the same place did last year. A marquee player holding out for an improved contract and the franchise playing hardball. The team finally decided to offer Nick Bosa a record deal and the holdout worked for the defensive end. This season Trent Williams and Brandon Aiyuk are engaged in a similar cold war with the 49ers, but Mike Florio believes the latter may have shot himself in the foot.

Wide receiver Aiyuk has been trying to get out of the final year of his contract with San Francisco for the best part of the last five months.  First, it was a holdout from OTAs and a mandatory training camp, then he requested a trade. In between he claimed the 49ers “don’t want me back” in a video on TikTok. But in an underwhelming turn of events, he decided to show up for the training camp. Florio thinks there is a line between  and Aiyuk has failed to meet the right balance.

Aiyuk has decided to use the hold-in strategy, which means he is attending Niners training camp to avoid getting fined but refusing to participate in the process. Instead of holding out for a new contract by skipping all team functions, Aiyuk has taken a different approach, but will it work?

“With the 49ers we know the drill. They react when you get their attention. Is a hold in going to get their attention or is a holdout going to get their attention? What happened last year? Nick Bosa held out, and he held out because the 49ers continued to drive a hard bargain. They want what they want. They ultimately gave in. Will they give in on Trent Williams? I’d say they’re more likely to give in on him than on Brandon Aiyuk because once you show up, you’re stuck. At some point, it’s time to get to work. At some point the player gives in,” opined Florio on Aiyuk and Williams’ situation on the NFL On NBC podcast.

One reason why Aiyuk reported to the training camp on July 23 was to avoid fines from the franchise. By already holding out from the three-day minicamp from June 4-6, he incurred a $101,716 fine. But he avoids that scenario by holding in. Nick Bosa was racking up $50,000 in fines for each training session he missed last year. Eventually, the fines were rescinded because Bosa was still on a rookie deal. There was a possibility of the same thing happening with Aiyuk, yet the WR chose to not take any chances.

Interestingly, Deebo Samuel employed the same tactic during the first few days of training camp in 2022, before settling on a three-year, $71.55 million extension.

Over the last two seasons, Aiyuk has emerged with 2,357 receiving yards and 15 TD grabs and it could make sense for him to wait out for an improved deal in the final year of his contract. He is currently expected to play on a $14.1 million club option in 2024. Several reports came out that the 49ers offered Aiyuke a new contract in the $26 million-per-year range in May, but Aiyuk is rumored to want a contract that is worth $28 million annually over the first three years.

Last year, Nick Bosa missed 37 days of training camp and eventually scored a 5 year, $170 million deal with the Niners. Aiyuk went on the same trajectory but eventually gave in. All the drama and speculation about him joining the Commanders with Jayden Daniels went down the drain. People can’t wrap their heads around why the WR requested a trade and still showed up for training. He’s not working out, but just watching the training from the sidelines.

Amidst the shenanigans, the 49ers can use a franchise tag on the WR. It’s projected to be around $22 million in 2025. Yet, there is no clarity whether Aiyuk will take the franchise tag or leave. After all, there should be no shortage of teams looking to hire this Super Bowl runner-up.

While Aiyuk did say the franchise “don’t want him back,” in the infamous TikTok video where he was Facetiming Jayden Daniels, it seems like the Niners do want him back, just not at the price he’s expecting. Also, the pattern is clear by now. The Bay Area team always wants to have an upper hand on all their players. Look at the kind of deal they offered Trent Williams.

Is Trent Williams winning in terms of contract negotiations?

The Niners gave the tackle a 6-year, $136 million extension in 2021. Williams has no guaranteed money left in his contract, and he’s looking for a way out of this situation. That’s because he may be released next year. Trent Williams is making $20.05 million this year as a base salary. The Niners will pay him even more in the next two years.

He’ll make $22.5 million in 2025 and $32.5 million in the next year. Subsequently, the Niners will have to cough up a lot of money to keep Williams happy. Kyle Shanahan knew all about this when he chose to address the media after training camp. Of course, the tackle wasn’t there in the facility. “Contract-related,” Kyle Shanahan said after Williams’ practice absence on Wednesday.

“John [Lynch] is speaking with his representatives; he has been doing it for a while” and didn’t clarify the situation further. But there’s another storm brewing, and the 49ers have to be prepared for what’s coming.

In the next two years, Brock Purdy is slated to make a generational deal with the 49ers. He’s proved his worth, and he’d want his team to reciprocate with the same energy. Then there’s the curious case of Deebo Samuel. Despite being a Super Bowl runner-up, he has an average salary of $23.8 million and would want to bump those numbers up from this year. The 49ers have their hands full for the next couple of years.

A couple of months ago, they asked Kyle Juszczyk and Arik Armstead to take a pay cut, and the players didn’t appreciate it. Coming back to Trent Williams, there’s something else that has to be addressed. He cannot rescind the $50k/day fines because he’s not on a rookie deal anymore. However, it feels like Trent Williams is in no mood to back off from his stance, unlike Brandon Aiyuk.

Should he be nice enough to participate in training, or should he stay out of the camp for his demanded deal? What do you think about the contract conundrum?