Kawakami: This 49ers negotiating season, the spotlight is on Jed York (2024)

You’re tested and evaluated every season and every day when you’re playing in the NFL, the way Brandon Aiyuk, Deebo Samuel, Christian McCaffrey and everybody in the San Francisco 49ers’ locker room are being evaluated at all times. The way Arik Armstead was evaluated and discarded by the team just a few months ago.

Are you good enough, are you dedicated enough, are you valuable enough, are you still valuable enough?

You’re tested just as much when you’re coaching or running the personnel shop, the way Kyle Shanahan and John Lynch are being judged and examined over every decision.

Jed York is the guy, in the end, who pays for all this and who is grading all these tests. But while owners can’t be fired, as York famously and accurately pointed out during a previous (and more chaotic) 49ers era, they’re constantly being tested, too.There are always challenges, even when the team is winning. Sometimes especially when the team is winning over a long period. Issues build up. The good times don’t come cheap. The bill eventually comes due.

And right now, Jed, the spotlight’s on you.

Considering the cost of what will get Aiyuk and McCaffrey on board for this coming season, the huge dollars the 49ers have already committed to Nick Bosa, Fred Warner, Trent Williams and George Kittle and the looming prospect of a mega deal for Brock Purdy next offseason, will York make the vast financial commitment necessary to keep most of this core together for a few more years? Or will the 49ers go through more problematic negotiations and high-profile departures in order to keep the costs from spiraling — but possibly costing the team some victories and maybe another Super Bowl shot or two?

None of it will be cheap. Aiyuk likely won’t sign for less than $24 million a year and probably $70 million guaranteed. McCaffrey, who, like Aiyuk, hasn’t been at the voluntary OTA sessions this month, might be a lot happier if the rest of his contract ($24 million over two years) was guaranteed plus another year added, instead of having his fate decided on a yearly basis from here on out. Next offseason, Purdy likely will land a deal in the vicinity of $45 million a year with $170 million or more guaranteed. Simple math says that York will be looking at more than $250 million in additional guaranteed money committed by the time a Purdy deal is done — just from three players.

Guaranteed money via signing bonuses and other cash agreements are what keep the immediate cap hits low. That’s how York, Paraag Marathe and Lynch have kept things salary-cap compliant to this point. But maybe at some near point, the 49ers will hit the ceiling of what York will want to pay out of his family’s bank accounts. Maybe the prospect of the Purdy contract is taking the Yorks to the absolute limit. And maybe McCaffrey and Aiyuk are feeling the tightening a bit right now.

Let me be clear here: York has not come up short in his spending at any previous time in the Shanahan/Lynch era, including multiple large contract extensions for both his coach and his GM. Thanks to Levi’s Stadium, the 49ers are a rich team that acts like it on the player-compensation market. Just look at the players acquired and salaries locked into this payroll and you can see why the 49ers have been a top-five cash-outlay team for most of the past five seasons. As the roster has improved and remained at the top, the 49ers’ salary structure has expanded with it.

But the 49ers of this era have never faced something like this. When the Yorks paid Jimmy Garoppolo at the top of the QB market in 2018, they didn’t have all these Pro Bowlers already making huge money. And one reason they committed to Trey Lance and got ready to move on from Garoppolo in 2021 was to set up a QB on a rookie deal while all these other big salaries started to escalate. When Lance faltered, Purdy’s emergence at his bottom-rung salary gave the 49ers several years of an economic grace period. But that is about to end. All teams want to have a QB who is worth $45-50 million a year, but it’s also something that must be budgeted around and planned for.

It’s a good thing to have so much talent. It’s a tricky thing to come to grips with how much it costs to maintain.

“There’s only one way around it, you’ve gotta have a committed ownership,” Williams said last August of the 49ers’ array of expensive talent. “That’s something (49ers ownership) will always handle; they will always find a way. There’s a plan up there. I leave that up to them. We’ve got the best front office in the NFL. I don’t even think it’s close. Look, we got Christian in halfway through the season. Highest-paid running back in the league. Who would’ve thought we could do that? Who would’ve thought you could pay Kittle that much money? Me that much money? Fred (Warner) that much money? Deebo?”

It’s certainly been free-flowing for the last few years. But the star players probably realize there’s a bit of a shift coming. If McCaffrey doesn’t get more money now, he might never get it — he’s about to turn 28, he’s been carrying a heavy offensive load at a position that isn’t valued much in the NFL, and all the 49ers know that Purdy’s deal next year will likely gobble up a huge percentage of the Yorks’ planned expenditures.

If McCaffrey just plays out this current contract, it’s a lot of money, yes. But next offseason, McCaffrey could be in the same place Armstead was in March, when the 49ers told him to take a huge pay cut or he’d be cut. Armstead refused, was cut and signed a new deal with the Jacksonville Jaguars. And what if McCaffrey gets hurt this season? What if, for whatever reason, his performance dips? He will never have the bargaining power he has right now.

Let’s see what York does about it in the next few months, and not just for McCaffrey.

Another large point: McCaffrey remains essential to everything Shanahan does on offense, and he’ll be essential whether the 49ers keep leaning into the running game or they ride with Purdy a little more through the air. McCaffrey might be heading into the final stages of his prime, but he also had the most rushing yards of his career last season (1,459) and second-highest career combined yards from scrimmage (2,023, tops in the league last year), behind only his epic 1,000-1,000 performance with the Panthers in 2019.

All by himself, McCaffrey accounted for a league-best 126.4 yards per game from scrimmage during the regular season.

McCaffrey also tied with Miami’s Raheem Mostert for the most touchdowns in the league last year, with 21, and was all alone at the top in first downs gained, with 114. (CeeDee Lamb was second in first downs gained, with 86. Aiyuk was second on the 49ers with 61. In Deebo’s incredible 1,771-combined-yards season in 2021, he had 72 first downs.)

And what would the 49ers’ offense have looked like in the playoffs without him? In three postseason games, McCaffrey had five total touchdowns and 420 total yards from scrimmage.

McCaffrey also might have some peer incentive to push the running-back market after years of complete stagnation, dating back to when he set the standard. When the Carolina Panthers signed McCaffrey to a four-year, $64 million extension in April 2020 (tacked on to the two years he still had remaining on his rookie deal), that made him the league’s highest-paid running back at an average of $16 million per year. That’s still No. 1 among RBs four years later.

In comparison, the top-paid receiver four years ago was Julio Jones at $22 million a year. Now, it’s Tyreek Hill with a $30 million average. Jones’ 2020 salary wouldn’t be in the top 10 for the position.

Is McCaffrey worth a fraction of Deebo’s $23 million average or less than half of Bosa’s $34 million per? I would say not. I’m relatively sure the 49ers would (quietly) agree. And guaranteeing a lot more of McCaffrey’s salary and getting it to him now wouldn’t hurt the 49ers’ cap situation at all, presuming they plan to have him on the team for a few more years. It’ll just be money that York has to pay out immediately when there’s also Aiyuk’s bonus money to consider and all the others.

According to Spotrac.com’s updated figures, the 49ers already have a $305 million cash commitment (base salaries plus bonuses paid out) for this season, fourth most in the league, behind only Cleveland ($339.7 million), Philadelphia ($332.2 million) and Detroit ($307.6 million). And those other teams already have large QB commitments. The 49ers have all this money tied up and they still have the Purdy deal to do next offseason, and they already have the fifth most cash committed ($217.5 million) for the 2025 season.

Again, the 49ers are looking at an unprecedented cash commitment coming up. If York is ready for it.

“It’s a tough business, for sure — you have to have thick skin,” Bosa said earlier this month when I asked about the 49ers’ release of Armstead when he wouldn’t take a huge pay cut and the trade talk surrounding Deebo and Aiyuk. “I think you have to understand that it is a business and the team is going to try to get as good as it possibly can with or without you and you have to look out for yourself. That’s why you go through holdouts and do things that seem selfish in the moment.

“But when everything is settled, we’re going to come together as a team and try to go get (a Super Bowl title).”

Before you start weeping for the York family (or any NFL owners), remember that Forbes’ most recent valuation of the 49ers was $6 billion (ranked ninth in the league) with an annual profit of $152 million. These are all estimates and I always hear complaints from all sides about how the numbers are put together; but under no circ*mstances are the 49ers anything less than massive revenue and profit generators. Just for context, which is the best way to view these estimates, Forbes valued the 49ers at $3.8 billion in 2020. That’s a 63.3 percent jump in four years.

The money is there. But I think we’re going to see some tussling over it in the next few months and years. We’ve already started to see it. And one of the main characters in the storyline, at least until the 49ers get to training camp in late July (and maybe even after that, if some star players are holding out into August), will be Jed York, who hasn’t done a lot wrong lately but has some massive checks to write if he wants to keep things going right.

(Top photo of Jed York and Christian McCaffrey after the 49ers’ NFC divisional round game against the Dallas Cowboys in 2023: Michael Zagaris / San Francisco 49ers / Getty Images)

Tim Kawakami is Editor-in-Chief of The Athletic's Bay Area coverage. Previously, he was a columnist with the Mercury News for 17 years, and before that he covered various beats for the Los Angeles Times and the Philadelphia Daily News. Follow Tim on Twitter @timkawakami