All 49ers and those tricky holdout/negotiation/Leeds United questions: Kawakami Mailbag, Part 2

Part 1 of this mailbag, featuring all the Giants, Warriors, A’s and Valkyries topics, posted earlier this week. On to Part 2 of this mailbag, which is focused strictly on 49ers questions and answers with their preseason finale coming up Friday evening.

As always, I tried to pick questions that were on the issues most frequently raised, though I had to cut off the sheer volume of contract-negotiation consternation at some point. Also, questions have been edited for length and clarity.

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I’m presuming Paraag Marathe is heavily involved in the Brandon Aiyuk negotiations at the moment. But how does the fact he is chairman of Leeds United affect this? — Robert O.

I’ll use this question as a launching point for a general line of concern I’ve heard from 49ers fans: Could the 49ers’ heavy investment in their Premier League team be affecting the amount of resources they can (or want to) pour into assembling their NFL roster?

It’s a logical question. Leeds certainly isn’t an inexpensive undertaking, and the first weeks of their season certainly must be consuming a lot of Marathe’s time while he’s also the point person for the 49ers’ major contract negotiations. But as I keep saying, the 49ers are a massively profitable enterprise. The Yorks are absolutely not in any financial trouble; they had to understand the financial responsibilities when they took on their Leeds investment. They can afford it because the NFL-side revenue stream is just that strong.

To put it bluntly, if the Leeds losses are affecting the Yorks’ willingness to commit enough guaranteed money to sign Aiyuk and Trent Williams this summer — if they need to squeeze even more profit out of the 49ers because they don’t like their overall bottom line once the Leeds debits hit — that’s the Yorks’ fault. Their NFL team is more than self-sustaining. It shouldn’t be limited by the Yorks’ other financial adventures. And I sure haven’t heard any rumblings of this.

The 49ers are currently holding the line on these negotiations, from everything I hear, because they want to make sure they’re not overcommitted on the cap and the guaranteed money going into the next two or three years, especially with a huge Brock Purdy deal coming down the line next offseason. It’s fair for Jed York to have a set amount of long-term guaranteed money he’s willing to put into escrow; the Purdy deal could add $125 million or more to that total next year. It’s also fair to scrutinize the 49ers if York’s total commitment isn’t enough to maintain a Super Bowl-level roster.

Kyle Shanahan and John Lynch are on board with this approach right now because they believe it’s right for their roster construction. They were maybe not so on board with the 49ers’ relative hardline in the Nick Bosa talks last year, and I think that helped lead to the 49ers’ cave-in to get Bosa signed days before the regular-season opener. But Shanahan and Lynch are OK with the situation now. We’ll see how it’ll feel if both stalemates go a few more weeks, though.

The time-commitment question for Marathe is another logical point to raise, but I sure haven’t heard that the Aiyuk and Williams situations are lacking Marathe’s attention. He’s involved in these talks. He’s definitely in on all negotiating strategy. There are other high-ranking figures — starting with Lynch — who are in these discussions, too. And it just takes one phone call or text — trans-Atlantic or otherwise — to get deals done. Those calls just haven’t been made yet. Maybe by next week.

Does Jed need to get approvals from his parents? His recent behavior seems more like the actions of John York, not Eddie DeBartolo Jr. — Michael P.

The 49ers have committed a lot of money in Jed’s tenure running this team. They’re making a ton, but they’re also paying out a ton (minus about $150 million a year in profits). That’s undeniable. He definitely wants to do what it takes to win a Super Bowl, and the 49ers have come very close three separate times. But he’s not his uncle, and these days an NFL team really can’t outspend its competitors on players like Eddie D. did, anyway.

Does Jed have budgets he wants everybody on the franchise sticking to? Yes. Definitely. I know 49ers employees who absolutely hear about it if they don’t adhere to those limits. And the York family doesn’t do the lavish stuff for team parties or just general employee benevolence that was a hallmark of the Eddie D. era. But none of the players whisper that the Yorks are cheap. Everybody understands it takes a lot of money to fund a good team, and we’ll see how far the Yorks will go this time.

Finally, does Jed have to check with his parents on big spending? I’m sure there are general outlines that most of the York family can peruse, but Jed not only is the public face of ownership, recently he took on the largest equity stake in the team and either will soon become the principal owner replacing his mother or already has done that.

Jed’s bet was building Levi’s Stadium. Once that became a money machine, his ownership preeminence in the York family was cast in stone.

Do you think the “hold-in” issue is big enough of a league-wide issue where that becomes discussed come the next CBA that owners try to find a way to fine players for it? — Eric T.

There’s no need for a CBA adjustment: Teams can fine players for reporting to camp but not practicing — if the players are healthy but refusing to practice until they get a new contract. But as Shanahan pointed out recently, we might call Aiyuk’s situation a hold-in, but Aiyuk himself told the 49ers that his back hurts and that’s why he’s not practicing. This is the general way it works with hold-ins across the league. You can guess that a back injury probably isn’t the actual reason Aiyuk isn’t practicing, but what’s an NFL team supposed to do? Call one of their best players a liar, start fining him and make everything worse?

There’s a reason only good players can pull off the hold-in ploy to avoid fines. Lesser players wouldn’t be given that leeway. Because good players are valuable. And while it surely isn’t a beloved situation, teams, coaches and executives accept it as long as they want to maintain a relationship with the players.

Why don’t the 49ers close down talks with Aiyuk and make him play (or not)? Sitting out this year makes no sense for him. I say it’s time to call his bluff. — Jon H.

If there’s no deal soon, things would get very problematic if Aiyuk continues to say his back hurts and the 49ers try to force him to play, anyway. It would be a worst-case scenario for both sides. It really could blow up the season and mess up Aiyuk’s career.

Do the 49ers want to risk that? Or do they believe that Aiyuk would capitulate in Week 2 or 3 and just play for his contracted $14.1 million this season and get to free agency next spring? I don’t have the answers to those questions. I think it would be very good for both sides to avoid this kind of showdown.

Assuming Aiyuk does re-sign, is anyone going to ask him why he went scorched earth this offseason in regards to his negotiations? — Tnt T.

Yes, someone will definitely ask Aiyuk that question if and when he signs a new deal. I’m always amused when fans demand that specific questions get asked — why wouldn’t reporters ask Aiyuk about the way this is being handled? I give you no assurances that he’ll answer it in any manner that will satisfy you, though.

But I think “scorched earth” is an inaccurate description for how Aiyuk has handled this. He hasn’t really criticized the 49ers (other than the “they said they don’t want me” social media thing). He hasn’t even said the names of York, Shanahan or Lynch during this entire period. And believe me, having covered a lot of these, when the player starts mentioning powerful people by name, that’s when things can get really, really bad.

This is more confusing than outwardly ugly. What I’ve heard from 49ers people is that Aiyuk’s camp has been extremely hard to read. The 49ers hate having to decipher social-media cues or wondering if the bro-hugs are just performances for the cameras. What I sense is that Aiyuk’s camp thinks the 49ers have been way too interested in “winning” this deal — in private and public — rather than getting him signed.

I just think the two sides have been talking past each other for months now. There’s a path to getting this solved. I think the two sides both separately understand this. I also think the two sides aren’t sure that the other cares or understands how to get there. There are a few days left before this might get really out of control.

It’s obvious that players like Deebo Samuel and Nick Bosa have performed poorly in their first year of big contracts after holding out. With such a small Super Bowl window and fine margins, isn’t it worth it to budge on a couple million a year to make sure Aiyuk (has) a full camp and (is) closer to 100 percent? — Camilo G.

I think so, yes. But it’s not my money. And I think the 49ers probably have recently moved up about a couple million a year. We’ll see if that’s enough to finalize this deal.

How much do the players really resent a player holding out for more money? — David P.

They don’t. In 99 percent of negotiations, even the really prolonged ones, players understand that each individual has to do what’s best for themselves and their families. It’s the respect each player would want for their own negotiations.

Do you think the 49ers negotiations with Williams/Aiyuk will be seen in a negative light by other potential free agents, harming their chances to sign others in the future? — Phani T.

If the 49ers offer the most money to a free agent, whatever happened in the months or years before that offer, they’ll likely sign that player. It’s about dollars almost every time. Secondarily, it’s about winning. If they win and offer the most money, the 49ers won’t have problems signing players.

Assuming the 49ers holdout saga continues: From a salary cap/planning perspective, does Aiyuk’s situation have to get settled first in order to proceed with Williams’ new deal? — Jason B.

No, there is no reason to believe that there are major cap issues that affect the timing of these deals. The 49ers are way under the cap. They will be under the cap after/if they sign Aiyuk and Williams, in whatever order it happens. Other than the available amount of money that the 49ers want to guarantee into the future, I think the Aiyuk and Williams negotiation overlap is mostly an attention issue. If the 49ers are focusing tons of time and energy on Aiyuk, for instance, that doesn’t leave much time to get the Williams deal across the finish line. Still could happen, but the time element to make deals is not infinite.

If Aiyuk and Williams both sign, how will that affect this year’s salary-cap surplus which can be carried forward to next year? — Mark H.

One thing I can’t repeat enough: New deals for either Aiyuk or Williams or both would lower their cap hits for this year, not raise them. That’s how big deals work in the NFL. Teams pay out bonuses coupled with lower base salaries to start the deals, and the bonuses are amortized through the life of the contract for cap purposes. For instance, the 49ers’ restructuring of Christian McCaffrey’s contract a few months ago gave him upfront money but also lowered his 2024 cap hit from about $14 million to under $7 million.

The Williams and Aiyuk situations are about guaranteed money and the cap two or three years into the future. Not about the 2024 salary cap.

When (it’s not if) Aiyuk signs, are you going to give Lynch, Kyle and Paraag credit for playing this negotiation out carefully and with as little drama as possible? — Tom J.

Gotta love when fans want an NFL team’s negotiating style to be praised even before anything has been solved with a very high-profile player. You just don’t get execs cheered like this during tough negotiations in other sports. The NFL Management Fandom is weird to me. Oh well.

Aiyuk requested a trade. The 49ers let him talk to other teams to try to get one done. That’s not drama? OK, it’s all probably a double-bluff, but if you go down that road and you’re called on it, you might end up having to do the trade and going into a very pivotal season without your best all-around receiver. Also, Aiyuk hasn’t practiced with the team since the Saturday before the Super Bowl. They haven’t had a situation like this other than Bosa. That’s not dramatic? Sheesh.

And I believe I’ve mentioned a few times that if I learn that playing hardball was the only way the 49ers could get this deal done, I’ll say so.

Assuming the Niners can come to an agreement on Aiyuk and Williams extensions for this season, which of their big contracts might they have to look to trade or get off the books when they do sign (Purdy) to his big deal next offseason? — Drew K.

When I recently asked George Kittle if this is something that he knows might happen to him eventually, he nodded immediately and said it’s just up to him to be too valuable for that kind of money jockeying. I’m not saying he’s the likeliest potential salary-trimming target next offseason, but I suspect the 49ers might be eyeing Kittle for a future pay cut now that he’s in his 30s. And as 49ers fans found out during the Arik Armstead situation, trying to force a veteran into a restructure/pay cut can lead to the player’s exit if he isn’t game to play along.

It also might mean letting Charvarius Ward go as a free agent next offseason and could lead to some very intense negotiations with pending free agents Deommodore Lenoir and Aaron Banks. The 49ers might have to restructure some other deals, too, if York is OK with adding more guaranteed money to the ledger. Fred Warner is always a candidate. Javon Hargrave’s deal was structured this year and could be restructured again. And next offseason, what about another multiyear extension for Deebo after we spent last offseason speculating that this would be his last one in a 49ers uniform? Again: Extensions usually decrease the immediate cap hits, not increase them.

Why can’t Dominick Puni play tackle? His measurables are pretty close to Williams. — Ron S.

I think maybe down the line Puni (who played left tackle last season at Kansas) could be an NFL tackle. But he was considered a guard prospect all the way through the draft process and is definitely a guard in the 49ers’ minds because he doesn’t have the longest arms or most agile footwork and doesn’t project to be a great edge protector. Given the size you note, I think he has some potential as a tackle, but the 49ers will be very happy if they can plop Puni in as a starting right guard in 2024 and go from there.

What are the chances the 49ers leave both Danny Gray and Ronnie Bell off the roster after the game against the Raiders? — Jimmy P.

I started this camp as a noted non-enthusiast about the NFL career paths of both Gray and Bell. And after watching them both again this year, I think this might be the end of the road for them on this team, unless something very dramatic happens on Friday night in Las Vegas or there are roster machinations I don’t expect.

If the 49ers keep six receivers on their 53-man roster, it’s likely Aiyuk, Deebo, Jauan Jennings, Jacob Cowing, Chris Conley and Ricky Pearsall. There are questions on this list, obviously, with Aiyuk’s contractual issue and Pearsall’s shoulder injury. There might be some shuffling for Week 1. But I can’t see Gray or Bell jumping over any of those guys straight up. And Trent Taylor is a better emergency punt returner than either of them, so he’s likely WR7.

Do you think Kyle Shanahan will ever humble himself enough to learn from his past mistakes? He’s still doubling down on his Atlanta Super Bowl days and that’s not a good thing. — Brian W.

Shanahan’s got to humble himself for the multiple times when he ended up coaching the second-best team in the NFL and was two or three plays away from being the best? How much do Dan Campbell, Matt LaFleur and all the other coaches who didn’t get that far have to humble themselves? Even more, I guess.

I understand that Shanahan has to win the big one to end up on any pantheon, and he hasn’t yet. He could’ve made one or two better decisions in both of the Super Bowl losses. He clearly will be criticized by many until he gets that ring. But just because a game is watched by more than 100 million people doesn’t mean it’s the only result that matters in a career. The other ones count, too, especially if you win a lot of them.

Who is your 49ers dark horse to make a significant impact this year? — Carlos M.

Conley is too obvious a choice because I talk about him all the time, though I suspect he’ll be involved in a handful of very important plays this year, just like he was last year.

For this question, I’ll go with Matt Barrows’ guy, backup tight end Eric Saubert. Unless there’s a big TE3 moment coming that I can’t quite foresee for Brayden Willis or Cam Latu (and the recent re-signing of Logan Thomas is maybe not a great sign for either guy), Saubert is essentially replacing both Charlie Woerner and Ross Dwelley on the game-day roster. That might lead to double-digit offensive snaps a game, tons of important special-teams reps and, hey, maybe a 49ers backup tight end who can catch 10-15 passes in a season. Amazing!

What are your thoughts on Colin Kaepernick possibly being a coach with the Chargers? — Christopher A.

I think it was a nice gesture by Jim Harbaugh to offer his old quarterback a coaching job, but it was never likely to be accepted. Kaepernick doesn’t want to make any decision that sounds like he’s accepting that his NFL career is over. It’s logical that taking a coaching job would signal that.

Would this be a possible career move for Kaepernick in later seasons, either on a Harbaugh staff or any other one? Maybe. But I don’t think Kaepernick’s future is in grinding through tape, blowing a whistle and being on the practice field every day as an assistant coach. And he doesn’t want to be any honorary figure on a football team. I think he has bigger plans with bigger ideas in mind, mostly not involving football (once he decides his playing career is over).

When are we going to get a 49ers “Hard Knocks”? Missed it during the Harbaugh era and concerned we may miss it in the Shanahan era, too. — Mark C.

I’ve joked that the day the 49ers get assigned to a “Hard Knocks” run is the day Shanahan and Lynch will quit. They hate the idea of cameras and microphones intruding into their meeting rooms and offices and recording private moments. They think it’ll warp the way they can talk to each other and to players. And they’ve been able to elude it because of the provision that playoff teams can block the assignment for the next two seasons.

Clearly, the NFL would love to have a signature franchise like the 49ers in this series. But if the NFL changes its rules to force the 49ers into it, I think we might see the coaching staff and GM totally boycott the thing and maybe the owners’ meetings, network-TV production meetings and anything else that the league wants them to do.

(Top photo of Brandon Aiyuk: Christian Petersen / Getty Images)