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All 49ers and those hard holdout/negotiation/Leeds United questions

This mailbag’s first part, which covered every Giants, Warriors, A’s, and Valkyrie topic, was published earlier this week. Now for Part 2 of this mailbag, which is exclusively devoted to 49ers questions and answers in light of Friday night’s preseason finale.

I made an effort, as usual, to select questions that addressed the most common concerns, albeit at some point I had to stop due to the overwhelming amount of anxiety around contract negotiations. Questions have also been rewritten to improve clarity and length.


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.

This query will serve as the basis for a general grievance that 49ers supporters have expressed: Could the 49ers’ significant financial commitment to their Premier League franchise be influencing the amount of money they are able to (or choose to) spend on building their NFL roster?

That is a reasonable query. Leeds is undoubtedly a costly endeavor, and Marathe is time must be heavily allocated to them during the first few weeks of the season, given that he is as the 49ers’ main point of contact for contract talks. However, as I have repeatedly stated, the 49ers are an extremely lucrative business. The Yorks had to acknowledge the financial obligations when they took on their Leeds venture, therefore they are in no way in financial difficulties. The money stream from the NFL is so robust that they can afford it.

To be blunt, the Yorks are at fault if their inability to commit enough guaranteed money to sign Aiyuk and Trent Williams this summer is a result of the Leeds losses. If they feel that the 49ers will have to make additional profits after the Leeds debits are realized, then they should be held accountable. Their NFL club can support themselves more than well. None of the Yorks’ previous financial misadventures should limit it. Furthermore, I have not heard any rumors about this.

According to what I have been told, the 49ers are holding off on these talks in order to ensure that they are not overcommitting to the cap and guaranteed money for the next two or three years, particularly with a big Brock Purdy deal expected to be announced during the offseason. Jed York should have a reasonable amount of guaranteed long-term funds that he is willing to place in escrow; the Purdy agreement may increase that amount by at least $125 million in the upcoming year. Examining the 49ers more closely is also appropriate if York’s whole dedication is insufficient to keep a roster worthy of a Super Bowl.

For the time being, Kyle Shanahan and John Lynch agree with this strategy because they think it will help them build their roster. They may not have agreed with the 49ers’ comparatively firm stance during the Nick Bosa negotiations last season, and I believe that contributed to the team’s eventual capitulation to sign Bosa only a few days prior to the start of the regular season. However, Lynch and Shanahan seem content with the current circumstances. But if these deadlocks persist for a few more weeks, we will see how that feels.

It makes sense to bring up Marathe is time commitment, but I have not heard anything to suggest that he is not paying enough attention to the Aiyuk and Williams problems. He takes part in these discussions. He is undoubtedly aware of every negotiation tactic. Other prominent individuals are also involved in these conversations, beginning with Lynch. And to close business, all it takes is a single phone call or text, whether across the Atlantic or not. Simply put, such calls have not been placed yet. Perhaps by the following 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.

Under Jed’s leadership, the 49ers have made significant financial commitments to this team. They pay out a lot of money in addition to gaining a lot of money (minus roughly $150 million in profits annually). That cannot be disputed. The 49ers have been in the hunt for a Super Bowl three times, and he is determined to go above and beyond to win one. However, he is not his uncle, and in any case, an NFL team these days can not afford to outspend its rivals on players of the caliber of Eddie D.

Does Jed have spending caps that he wants all of the franchise members to meet? Indeed. Without a doubt. If 49ers employees do not follow those guidelines, I know they will be told about it. Furthermore, the York family does not engage in the extravagant team-building activities or general employee kindness that characterized the Eddie D. era. However, not a single participant murmurs that the Yorks are inexpensive. Everyone knows that a competent squad requires a large financial commitment; we shall see how far the Yorks are willing to go this time.

Lastly, about large purchases, does Jed need to consult his parents? There are probably broad synopses available for the majority of the York family to review, but Jed is not simply the team’s public face; he recently acquired the biggest equity interest and is either about to replace his mother as the team’s principal owner or has already done so.

Constructing Levi’s Stadium was Jed’s wager. His ownership dominance inside the York family was cemented once that turned into a money-making machine.

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.

A CBA change is not necessary because teams have the authority to punish players who show up for camp without practicing, provided that the players are healthy and will not practice until they sign a new contract. However, as Shanahan previously noted, while we may label Aiyuk’s circumstances as a hold-in, Aiyuk himself informed the 49ers that he is not practicing because of back pain. This is how hold-ins generally operate throughout the league. You may undoubtedly assume that Aiyuk’s lack of practice is not really due to a back problem, but what can an NFL team do? Make things worse by calling one of their top players a liar and fining him?

The hold-in technique to avoid fines is only effective by skilled players for a reason. It would not be extended to lesser players. why talented athletes are prized. Even while it is undoubtedly a difficult scenario, teams, executives, and coaches put up with it in order to keep a relationship with the players.

Brandon Aiyuk set a career high in receiving yards last year with 1,342. In the final year of his deal, he’s still holding out as the preseason nears an end. (Christian Petersen / Getty Images)

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 a deal is not reached quickly, things might get very serious if Aiyuk keeps complaining that his back hurts and the 49ers try to make him play despite that. For all parties, it would be the worst-case situation. It has the potential to ruin Aiyuk’s career and blow up the season.

Should the 49ers take that chance? Or do they think that Aiyuk will give up in Weeks 2 or 3 and simply play this season for his $14.1 million deal, which will allow him to enter free agency the following spring? To those questions, I have no answers. I believe that avoiding this kind of confrontation would be beneficial for all parties.

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, if and when Aiyuk gets a new contract, someone will undoubtedly ask him that question. I find it funny when fans insist on asking particular questions; why do not reporters confront Aiyuk about how this is being handled? But I can not promise that he would respond to it in a way that pleases you.

However, I do not think that Aiyuk’s approach to this situation can be described as “scorched earth.” Apart from the social media post stating that “they said they do not want me,” he has not actually criticized the 49ers. Throughout this whole time, he has not even mentioned the names of York, Shanahan, or Lynch. After going over a number of these, I can assure you that things may get really, really nasty when the player begins naming prominent figures.

This is less obviously awful and more perplexing. People who follow the 49ers have told me that it is been very difficult to follow Aiyuk’s camp. The 49ers detest having to interpret clues from social media or questioning whether the group hugs are staged for photo ops. I get the impression that Aiyuk’s side believes the 49ers have been far more focused on “winning” this contract—both behind closed doors and in the open—than on signing him.

Simply put, it seems like the two sides have been speaking over one another for months. There is a way to resolve this. I believe that each party is aware of this on its own. Additionally, I believe that neither side is certain the other is interested or knows how to get there. There are still a few days until things could spiral out of hand.

It is clear that after holding out, athletes like Nick Bosa and Deebo Samuel have underperformed in their first year of large contracts. Given the tight margins and short window for the Super Bowl, would not it be worthwhile to give up a few million dollars year to ensure that Aiyuk has a complete camp and is closer to 100 percent? — Camilo G.

Yes, I believe so. It is not my money, though. Furthermore, I believe the 49ers have just increased their salary by a few million dollars annually. We will check to see if that closes this agreement.

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

They don’t. 99 percent of the time, throughout even the longest conversations, the parties involved agree that each person must act in their own best interests and those of their families. It is the deference every participant would expect to their own talks.

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.

Regardless of what transpired in the months or years before to that offer, the 49ers will almost certainly sign the player if they make the highest salary offer to a free agency. Almost often, it is about money. It is about winning secondly. The 49ers will not have any trouble signing players if they prevail and make the highest salary offer.

With no guaranteed money left on his deal, 11-time Pro Bowler Trent Williams is also seeking a reworked contract with the 49ers. (Kevin Sabitus / Getty Images)

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 not any evidence to suggest that significant cap difficulties influence when these agreements happen. The 49ers have far less than the cap. Regardless of the sequence in which they sign Williams and Aiyuk, they will be below the cap. The 49ers’ desire to secure a certain amount of money for the future aside, I believe the main reason for the Aiyuk and Williams negotiation overlap is attention-grabbing. There will not be much time left to complete the Williams deal if the 49ers are devoting a lot of time and effort to Aiyuk, for example. It is still possible, but there is a finite amount of time to close deals.

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.

I can not stress this enough: Any new agreements for Williams, Aiyuk, or both would reduce, not increase, their cap impacts for this year. In the NFL, major agreements operate like this. To begin the deal, teams offer bonuses in addition to reduced basic wages; for cap reasons, the bonuses are amortized over the contract’s duration. Christian McCaffrey, for example, received upfront compensation when the 49ers restructured his contract a few months ago, but it also reduced his 2024 cap hit from almost $14 million to less than $7 million.

The guaranteed money and the cap two or three years from now are the focal points of the Williams and Aiyuk scenarios. Not the 2024 pay ceiling, that is.

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.

It is amazing when supporters of an NFL team want to applaud the team’s negotiation strategy before a high-profile player’s contract has been finalized. Executives are not cheered during difficult talks in other sports, that is for sure. I find the NFL Management Fandom to be strange. Well, anything.

Aiyuk asked to be traded. To try to complete one, the 49ers allowed him to speak with other teams. Is that not a dramatic situation? Well, that is all probably a double-bluff, but if you proceed in that direction and get caught, you may find yourself needing to make the trade and missing out on your greatest all-around receiver going into a crucial season. Aiyuk has not worked out with the club since the Saturday before the Super Bowl, as well. Other than Bosa, they have not encountered a circumstance like this. Is that not a dramatic statement? Haha.

And I think I have said before that I will speak up if I find out that the 49ers’ only chance to close this transaction was by playing hardball.

Which of the big contracts for Aiyuk and Williams may the Niners need to look to move or get off the books when they do sign Purdy to his big deal next offseason, assuming they can reach an agreement on their extensions for this season? —Drew.

George Kittle nodded instantly when I asked him lately if he knew this was something that would happen to him later and that it was up to him to be too important for that kind of money-chasing. While I would not say he is the 49ers’ most likely target for contract reduction in the upcoming offseason, I do think they may be considering Kittle for a future pay decrease given that he is in his 30s. Additionally, forcing a veteran into a restructuring or pay cut if he is not willing to comply might result in the player’s departure, as 49ers supporters learned during the Arik Armstead incident.

Additionally, it might mean releasing Charvarius Ward as a free agent in the upcoming offseason, which might result in some heated talks with Aaron Banks and Deommodore Lenoir, two prospective free agents. If York agrees to add additional guaranteed money to the ledger, the 49ers may need to rework some other agreements as well. Fred Warner is a candidate at all times. The terms of Javon Hargrave’s contract were set this year and may change in the future. And after assuming that this would be Deebo’s final offseason in a 49ers uniform last offseason, how about another multiyear agreement for him next offseason? Reiterating: Extensions typically result in fewer immediate cap hits rather than more.

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

Puni, who played left tackle for Kansas last season, has the potential to become an NFL lineman in the future, in my opinion. Despite not having the longest arms or the most nimble footwork, he was viewed as a guard prospect throughout the draft process and is still viewed as such by the 49ers since he does not project as a terrific edge protector. Though I believe Puni has some potential as a tackle given his size, the 49ers would be thrilled to have Puni start at right guard in 2024 and grow 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 was, going into this camp, a well-known non-enthusiast regarding Gray and Bell’s NFL careers. And after seeing them both again this season, I believe that, barring some really unexpected roster machinations or something extremely dramatic happening on Friday night in Las Vegas, this may be the end of their time on this team.

The six receivers that the 49ers will probably keep on their 53-man roster are Aiyuk, Deebo, Chris Conley, Ricky Pearsall, and Jauan Jennings. Naturally, there are concerns over this list, including Aiyuk’s contractual dispute and Pearsall’s shoulder injury. For Week 1, there might be some changes. However, I do not see Gray or Bell easily outclassing either of those men. Trent Taylor is probably WR7 since he is a superior emergency punt returner than both of them.

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 needs to take responsibility for the numerous occasions in which he was only two or three plays away from leading the NFL’s top team while guiding the second-best squad. To what extent do Matt LaFleur, Dan Campbell, and the other coaches that fell short have to humble themselves? More, I suppose.

I am aware that Shanahan has not yet entered any pantheon and that he needs to win the major one to do so. In each of the Super Bowl defeats, he had the opportunity to make one or two wiser choices. Until he receives the ring, he will undoubtedly face criticism from many. However, a game’s viewership of over 100 million does not indicate that it is the only outcome that matters in a career. The rest are also significant, particularly if you win a large number of them.

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

Conley is too obvious a choice—I talk about him all the time—but I have a feeling that, like last year, he will be on a few really significant plays this year.

Eric Saubert, Matt Barrows’ backup tight end, is my choice for this question. Saubert is essentially replacing both Charlie Woerner and Ross Dwelley on the game-day roster, unless Brayden Willis or Cam Latu have a huge TE3 moment that I can not quite predict (and Logan Thomas’ recent re-signing may not be a positive indication for either guy). That may result in double-digit offensive plays per game, a ton of crucial special teams reps, and, who knows, maybe a backup tight end for the 49ers who can catch ten or more passes in a season. Fantastic!

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

Though it was unlikely to be accepted, I thought Jim Harbaugh’s offer to coach his former quarterback was a kind gesture. Kaepernick is unwilling to make any moves that would suggest he is given up on his NFL career. It makes sense that accepting a coaching position would indicate that.

Is there any chance that Kaepernick might make a move like this in the future, either with the Harbaugh team or another one? Perhaps. However, I do not believe that Kaepernick will continue to sift through footage, sound the whistle, and work as an assistant coach every day on the practice field. Additionally, he has no desire to hold any honorific status on a football squad. I believe he has greater ideas and goals, most of which have nothing to do with football (once he decides his playing career is ended).

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 have made jokes that Shanahan and Lynch will resign the day the 49ers are assigned to a “Hard Knocks” run. They detest the thought of having microphones and cameras bug their workplaces and conference rooms to record intimate moments. They believe it will distort their ability to communicate with gamers and with one other. And the clause allowing playoff teams to block the assignment for the following two seasons has allowed them to avoid it.

It is obvious that the 49ers are the type of iconic team that the NFL would want to have in this series. However, I believe that if the NFL modifies its regulations to compel the 49ers to participate, the coaching staff and general manager will likely completely boycott the event, as well as any owners’ meetings, network television production meetings, and other league-mandated events.

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

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