Kawakami: 49ers have buyer’s remorse with Brandon Aiyuk

The San Francisco 49ers have begun a bit of a roster purge this offseason. How extensive that purge will be remains to be seen, but the team has already agreed to trade wide receiver Deebo Samuel. The move aligns with general manager John Lynch and head coach Kyle Shanahan's apparent desire to get younger.

Some believe Samuel might not be the only high-priced receiver on the trading block. Reports suggest the 49ers are open to moving Brandon Aiyuk, who signed a lucrative contract extension last year, making him one of the NFL's highest-paid wideouts. However, trading Aiyuk presents challenges—he's coming off ACL and MCL injuries, and when you combine that with his hefty contract, his trade market may be limited.

Tim Kawakami of The San Francisco Standard joined Bay Area radio station KNBR on Thursday and shared that the 49ers have buyer's remorse regarding Aiyuk's deal.

"There's absolutely tension that still lingers over that negotiation last summer, into the fall," Kawakami said. "And they did not like the price that they paid for him."

The organization likely felt significant pressure to finalize the deal, as it wanted to avoid the drama of Aiyuk's holdout (or hold-in) spilling into the regular season. Ultimately, the two sides agreed to terms just before Week 1.

The 49ers also had high expectations after coming off a Super Bowl appearance and falling just short of a championship.

"I think it was, let's go for it, we're going for the Super Bowl, from the football side," Kawakami continued. "And I think the negotiators never felt good about that number, ever, $30 million a year. I think they were ready to trade him multiple times last year, maybe even the year before."

Kawakami acknowledges that while Aiyuk is a talented player, the circumstances make it difficult for the 49ers to get significant value in return if they pursue a trade, especially with Aiyuk potentially missing the start of the 2025 season.

"That's a tough one, and you're going to trade both Deebo and Aiyuk?" Kawakami said. "I'll just say the general theme here is the 49ers' top not being happy with those deals, not being happy with a lot of deals, not being happy with the money that they've paid, as John Lynch talked about in Indianapolis."

While Kawakami doesn't consider this offseason a full rebuild, he sees it as a "recalibration" or "reassessment."

"I don't think they're saying we're not going to pay any money to anybody," Kawakami added. "I just think that they're thinking it's going to have to be for value, and they don't feel it right now. I don't think they're trading Aiyuk. They still might. Who knows? But it's going to have to be for something of value, and they're going to have to figure out how they're going to get another wide receiver in there, or another two, and we'll see how that goes."

According to Kawakami, there is growing frustration inside the organization about the amount of money spent over the years in pursuit of a Super Bowl—only to fall short repeatedly.