When do 49ers begin worrying about Nick Bosa contract talks?

Nick Bosa and the 49ers haven't come to an agreement about a new contract, and patience is eventually going to wear thin.

General manager John Lynch and the San Francisco 49ers knew contract talks with All-Pro edge Nick Bosa were going to get complicated and potentially messy.

After all, the reigning Defensive Player of the Year who led the NFL with 18.5 sacks last season is poised to become the highest-paid non-quarterback in league history in the very near future. His contract should easily surpass $30 million, annually, and it wouldn't be shocking to see something in the range of $35 million per year.

Not surprisingly, Bosa isn't attending Niners training camp and will hold out until he gets his extension. And while the current collective bargaining agreement allows for significant per-day fines regarding holdouts, Bosa being on his fully guaranteed fifth-year option negates that.

And, so, the standoff.

Lynch has told reporters that he's keeping the details of contract negotiations quiet, citing his own experiences as a player, which means we don't know much. And Lynch keeps stressing the need to be patient.

But is it that easy?

Is there a deadline for the 49ers to extend Nick Bosa?

Contract extensions aren't like franchise tags where players have certain deadlines to sign the tag, and teams also have a window in which they can negotiate with tagged players for a long-term deal.

Technically, Bosa is under contract for 2023 on that aforementioned fifth-year option that'll pay $17.86 million, according to Over the Cap.

OTC says those daily fines can be $40,000. Yet San Francisco can elect to waive those.

Preseason and regular-season games, however, can incur weekly fines equivalent to a player's weekly salary, which is $949,389 in Bosa's case, per OTC.

The 49ers may not care about Bosa missing preseason games. But if the holdout stretches into the regular season, it'd likely be a pretty costly decision on the pass-rusher's part.

Why the 49ers should worry about Nick Bosa (and why they shouldn't)

The Los Angeles Rams' recent renegotiation with perennial All-Pro defensive tackle Aaron Donald reset the top-defender market by more than 13 percent, as OTC pointed out, giving Donald nearly $32 million annually, $4 million above Pittsburgh Steelers edge T.J. Watt's recent blockbuster deal.

Bosa's agent, Brian Ayrault, is likely going to seek that same kind of increase, if not more, for his client. Considering the Niners have $9.6 million in cap space, currently, and are projected to be above the cap by $13 million in 2024, it's safe to say Lynch and Co. have their financial work cut out for them.

There's a solid chance no deal can be reached, especially in terms of guarantees and incentives. Bosa could have simply priced himself well beyond San Francisco's comfort range and even beyond the point of making a significant contractual stretch.

And that might potentially lead to a similar situation not unlike what the 49ers experienced with Pro Bowl defensive tackle DeForest Buckner ahead of the 2020 season when both sides couldn't reach a long-term contract, and Buckner was subsequently traded away to the Indianapolis Colts for a first-round NFL Draft pick.

However...

Bosa is a generational talent. Both sides know this, yet the Niners do have the advantage of getting ahead of what'll likely be only a growing market for top-end pass-rushers. In three or four years, Bosa's contract will probably look like a relative bargain.

All the while, the NFL salary cap will only increase. If that's not the lone reason for optimism, the Buckner case is a bit of an outlier. Typically, as has been the case with most of their top talents, the Niners have been able to financially figure out long-term deals that satisfy both player and team.

While there's a good reason to start the concern over Bosa's contract, the stronger likelihood is that a deal will get done prior to the start of the preseason, which won't commence until Sunday, Aug. 13.

A lot can happen between now and then.

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