A significant reason for the vibes being off in training camp for the San Francisco 49ers was due to the holdouts of Brandon Aiyuk and Trent Williams.

It brought unnecessary drama and didn’t allow the 49ers to build cohesion with their offense. Somewhat of the same can be said about Christian McCaffrey. He missed almost all of training camp with a calf injury. Eventually, it was revealed to be an Achilles injury.

What a coincidence that the three star players the 49ers extended in the offseason were major reasons for the season being disappointing. It’s probably crossed the 49ers’ minds that they wish they didn’t agree to at least one deal.

Which 2024 contract extension do the 49ers regret the most?

It has to be McCaffrey. 2024 was a down year for the 49ers partly because he dealt with a bilateral Achilles injury. I suspect McCaffrey had an idea of this and didn’t divulge it to the 49ers when he received his extension last June. Or maybe he did reveal it and the 49ers didn’t care.

McCaffrey was only active for four games with his fourth game being cut short due to a patellar injury. His Achilles didn’t look to be too much of an issue. There was a noticeable lack of burst from him and some hesitation, but that could be more of a mental aspect of being afraid to tear his Achilles.

McCaffrey’s Achilles didn’t end his 2024 season, but it will continue to be under the microscope heading into 2025 as opposed to his knee. It will never go away until he tears it or looks like his 2023 version. There is a chance the 49ers never get that version of him again because of his Achilles.

So, the 49ers will have cashed out a player who might not be the same again or will have to miss significant time. Regardless of the information of Achilles being known or not, McCaffrey is an extremely high-risk, high-reward situation.

Now, Aiyuk might be the player many fans choose as the regretful contract. Jauan Jennings ascended this season and Ricky Pearsall may be on the rise. However, it still made perfect sense for the 49ers to extend Aiyuk. Their logic was sound. They wanted to tie him to Brock Purdy for years to come.

Every good quarterback has a go-to receiver and Aiyuk was that guy for the 49ers. Plus, he was their best if not only man-coverage-beating wide receiver. Sure, he wasn’t productive when he played this year and had some drops, but it’s not like he would remain that way.

Defenses were still scheming around Aiyuk, so he had a positive impact. It’s just unfortunate now that he suffered significant injuries to his knee. Believing Aiyuk is the most regretful contract is complete revisionist history and prisoner of the moment.

Williams would make sense instead of McCaffrey too since he’s closer to retirement than not. Injuries are becoming frequent and tough to recover from for him. He missed the final seven games of the season due to an ankle injury that was extremely slow to heal.

Despite all of those concerns, the 49ers had to roll the dice on Williams given he’s still one of the best offensive tackles when active. Not to mention the 49ers didn’t have an alternative for him in place, so it’s ideal not to upset one of the best players on the team who is responsible for protecting Purdy.

McCaffrey has to be the most regretful extension. I get how beloved he is and how phenomenal he’s been since joining the 49ers. Yet, it cannot be downplayed how concerning his Achilles will be. No matter what he and the 49ers say, it will always be a question and concern with him in 2025 and beyond.