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Can 49ers, Chiefs keep their stars? Free agents, extensions

The challenge for the great teams in a salary cap league is staying great.

In the NFL, as players start to play better and help teams compete for and win Super Bowls, they obviously start to deserve more money. The trick is to re-sign stars or replenish with draft picks, and deciding when to take each path is what makes cap management a jigsaw puzzle. The best teams often seem to be the ones with the toughest decisions.

That brings us to the 2023 season's Super Bowl teams. The Kansas City Chiefs and the San Francisco 49ers gave us an all-time classic matchup that we'd love to see again. But while it's possible these two teams could meet in the Super Bowl again next season in New Orleans, it's not going to be easy. And even if they can get there, the odds are they'll both look different.

The Chiefs and 49ers each have key free agents they need to decide whether to re-sign or let walk. They both have stars who are due for contract extensions, either this offseason or very soon. And neither has a ton of cap space.

But yes, it can be done. Both the Chiefs and 49ers have the ability, with some salary cap maneuvering, to pay everybody and bring back their Super Bowl rosters. It won't be easy, and I'm not sitting here saying that's what will happen. But we wanted to map out a couple of blueprints for how the Super Bowl LVIII participants can keep their rosters together. Let's start with the champs.

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Kansas City Chiefs

Key free agents: DT Chris Jones, CB L'Jarius Sneed, LT Donovan Smith, LB Willie Gay, DT Derrick Nnadi, RB Jerick McKinnon, RB Clyde Edwards-Helaire, S Mike Edwards, WR Mecole Hardman, P Tommy Townsend, DE Mike Danna, G Nick Allegretti, LB Drue Tranquill

Extension candidates: LB Nick Bolton, C Creed Humphrey, G Trey Smith, TE Noah Gray

Potential cuts for cap savings: WR Marquez Valdes-Scantling, S Justin Reid, DE Charles Omenihu

Top priority: The key issues are the first two names on that list of free agents. Jones is the team's best player not named Patrick Mahomes, and his game-wrecking performance in the Super Bowl only underlined his value. He has 26 combined sacks over the past two seasons. The two sides were unable to reach agreement on a long-term contract extension last offseason, and that dispute lasted long enough that Jones actually sat out all of training camp and the first game of the regular season, incurring millions of dollars in fines. He ultimately signed a one-year deal.

The Chiefs theoretically could use the franchise tag on Jones this offseason, but it would cost them $32.16 million. They also have to account for the $4.25 million option bonus they just picked up. With the way that works, that charge is spread out over five years from 2023 to '27 for cap purposes. But since the remaining years on Jones' contract void next week, the remaining 80% of it ($3.4 million) accelerates onto their 2024 cap. So the Chiefs would have to carry a salary cap charge of $35.56 million for Jones if they franchised him.

That all means the preference would be doing a long-term extension that kept the 2024 cap number more manageable. If they tag Jones, the general belief is that they won't have enough money to re-sign Sneed, who could fetch upward of $18-19 million per year on a new deal if he hit the open market.

What about Sneed: Sneed is one of the league's top corners and a key part of the Chiefs' defense (nine pass breakups last season and 10 career interceptions), so he wouldn't be easy to replace. But the Chiefs have drafted four cornerbacks in the past two drafts, including 2022 first-rounder Trent McDuffie, who appears more than ready to take over as the No. 1 corner if Sneed leaves. Their draft strategy has been preparing them for the possibility of this happening. Jones, who is the key to their pass rush and a top-five defender in the league, seems to be more difficult to replace than Sneed.

As of now, according to Roster Management System, the Chiefs project to be about $21.2 million under the 2024 cap. (The 2024 cap number isn't set yet, but most teams around the league seem to be working with a projected cap of $242 million.) They'd need to clear space if they wanted to fit in Jones' franchise tag.

The Mahomes factor: One of the best assets the Chiefs have at their disposal for these moves is Mahomes' contract, which has eight years left on it and affords them the perpetual ability to convert salary to bonuses and clear cap room. If the Chiefs did a full restructure on his 2024 compensation -- converting all but the required $1.21 million veteran minimum salary to a signing bonus and also converting his $34.9 million roster bonus to a signing bonus -- they'd reduce his 2024 cap number from its current $58.6 million to around $23 million. That savings alone would increase their projected cap space to about $57 million. Put simply, the savings from that restructuring of Mahomes' contract, which is inevitable, is almost exactly the same as the cap cost of Jones if they franchise him.

So once that's done (and again, this assumes the Chiefs don't get an extension done with Jones and have to franchise him), the Chiefs would be back down to roughly that original $21.2 million in cap space. This would easily afford them enough room to re-sign Sneed if they wanted. We can use last year's Trevon Diggs extension with the Dallas Cowboys as an example. Diggs got a five-year, $97 million extension with $33.3 million fully guaranteed at signing, including a $21.25 million signing bonus. Let's be generous and say Sneed gets $1 million more per year, giving him five years and $102 million with, say, a $25 million signing bonus. His cap number for 2024 on a structure like that would be $6.125 million.

The Chiefs might not want to do a top-of-market deal for Sneed -- they've been preparing for his potential exit for the past couple of years and may just let him walk. I'm just trying to explain how they could keep both Jones and Sneed. In our example, with Jones on the franchise tag and Sneed on a fat new contract, the Chiefs still have just over $15 million in cap space with which to operate the rest of their offseason.

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More moves needed: Of course, just returning Jones and Sneed isn't enough. If the Chiefs want to bring back some of those other free agents -- Gay, Townsend, Edwards, Nnadi and more -- that cap space will dry up quickly. And teams generally need to hold open something like $5 million to $6 million to account for their draft picks. Plus, the Chiefs have other needs. If Donovan Smith isn't re-signed, they will need a left tackle. They could use more help at wide receiver. Those aren't cheap positions to fill in free agency. And there's no cap room to be found in potential extensions for 2022 draft picks Bolton, Humphrey and Trey Smith, each of whom at this point is entering the fourth year of his relatively low-cost rookie contract.

That's where other avenues for potential savings come in. Releasing Valdes-Scantling would save $12 million in cap space, though it would also deepen their need at wide receiver. Releasing Reid would save $10.75 million in cap space (they've drafted two safeties over the past two years as well). Omenihu, who tore an ACL in the AFC Championship Game and might not be ready to start the regular season as a result, has no guaranteed money left on his contract, and as cold as it might be, they would save $7.22 million if they cut him. (Note: $2 million of Omenihu's $6.74 million salary becomes guaranteed on March 16, so Kansas City would have to make this decision fairly soon.)

I'm not saying the Chiefs will or even should cut all three of those guys, but if they did, that's another nearly $30 million in cap space. That takes them back up to around $45 million, which they could use to sign free agents, extend their own guys and sign their draft picks. And that number could go higher if they were to restructure the contracts of guard Joe Thuney (about $7.5 million more in cap savings) and right tackle Jawaan Taylor (about $12.6 million more) and/or restructure or extend tight end Travis Kelce ($5.5-8 million more).

A couple of additional notes before we move on to San Francisco:

  • You might be yelling, "Kadarius Toney!" Why not cut the struggling receiver? Well, they might. His performance was that bad (five drops and just 169 total yards last season). But the Chiefs wouldn't save any cash or cap space by cutting him. As a 2021 first-round pick, Toney's entire four-year rookie contract was fully guaranteed. So the Chiefs have to pay him his $2.53 million salary for 2024 (and count it against the cap) even if they release him.

  • The contract of Taylor is worth a mention, too, because the right tackle and his agent, Drew Rosenhaus, did a pretty sweet job on this one. Taylor is owed $20 million in guaranteed money in 2024, which means it would actually cost the Chiefs more against the 2024 cap to cut him than it would to keep him. But where Taylor really won here was with this little beauty: As of the third day of the 2024 league year (March 16), Taylor's $20 million in 2025 salary becomes fully guaranteed. This effectively ties the Chiefs to Taylor (who was flagged for 19 penalties last season) through at least 2024, and likely longer. Their best play here may be to move him to left tackle to replace Donovan Smith and find a cheaper option to play on the right side.

The most likely outcome: Even though it's possible for the Chiefs to keep both Jones and Sneed, the prediction here is that they won't. I think they will find a way to keep Jones, since he's just that irreplaceable, even if it's just taking his franchise tag number and doing a one-year deal with four void years on the end of it to lessen the short-term cap impact.

If that happens, my prediction is Sneed leaves and gets his big deal elsewhere. Kansas City let Charvarius Ward leave in free agency at the end of his rookie contract three years ago in part because Sneed was on the way. Now, with McDuffie and others ready to move up, it feels like the Chiefs are prepared to let Sneed leave and use that money elsewhere. Circle of life.


San Francisco 49ers

Key free agents: DE Chase Young, DE Randy Gregory, WR Jauan Jennings, G Jon Feliciano, DT Javon Kinlaw, S Tashaun Gipson Sr., DB Logan Ryan

Extension candidates: WR Brandon Aiyuk, S Talanoa Hufanga, LB Fred Warner, CB Charvarius Ward, LB Dre Greenlaw, G Aaron Banks

Potential cuts for cap savings: FB Kyle Juszczyk, RT Colton McKivitz, C Jake Brendel, CB Isaiah Oliver, Greenlaw (yes, he's also on this list)

Top priority: Aiyuk's situation looms the largest over this 49ers offseason, and if they can't find a way to a contract extension, the talented wideout could theoretically ask to be traded to a team that's willing and able to pay him. I want to stress that this is speculative: I do not know whether Aiyuk will want out if his contract is not extended. But I do know it's not going to be easy for the Niners to extend him and that other wide receivers in similar situations in recent years -- such as Davante Adams, Tyreek Hill and A.J. Brown -- have asked to be traded and gotten their wish.

The 49ers head into the offseason projected to be about $7.5 million over the projected cap, according to Roster Management System. This is in part due to $5.5 million in leftover Trey Lance dead money they can't do anything about. So they have to do some work to get under the cap before they can operate their offseason.

Doing an Aiyuk extension right now could actually help. After 1,342 yards last season, the 2020 first-rounder will now be entering his fifth-year option season and is scheduled to earn $14.124 million, which is also his cap number. Extending him could drop his 2024 cap number by as much as $10 million.

The problem is, the wide receiver extension market hasn't moved much since the 2022 offseason, and it has been tough for teams to find common ground with the likes of Justin Jefferson, CeeDee Lamb, Michael Pittman Jr. and Tee Higgins. So it's difficult to project the terms of a potential Aiyuk extension until we see what happens elsewhere in that market. And unless the Niners are willing to blow Aiyuk away with an offer that could turn out to be an overpay, he probably wants to wait and see some of those other guys set the market.

Additionally, while doing an extension would reduce Aiyuk's 2024 cap number, the Niners have to be cognizant of what it would do to his future-year cap hits. One of their key salary cap assets at the moment is the contract of starting quarterback Brock Purdy, who's scheduled to count just $1.004 million against the cap in 2024, when he earns $985,000 in salary. Collective bargaining agreement rules prohibit the Niners from doing a Purdy extension until after the 2024 season, at which point they will likely have to extend him, making his cap number more of an impediment than an asset. Even if the 49ers can do an Aiyuk extension this offseason, they might be better off finding a way to dump a chunk of the cap hit into 2024 rather than floating it down the road.

Other options: San Francisco could get cap relief elsewhere. Pick a veteran deal to restructure. Left tackle Trent Williams has a 2024 cap number of $31.569 million, which could be reduced by as much as $17 million with a simple rework. Wide receiver Deebo Samuel has a cap number of $28.634 million, which could be reduced by as much as $15 million. The 49ers could save as much as $12 million by knocking down defensive tackle Arik Armstead's $28.353 million cap number with a restructure. And they could save about $11 million with a restructure or extension of Warner's deal, which voids after 2024.

Let's start at the top. We'll say the Niners restructure Williams and Samuel to save about $32 million in cap space. That puts them about $24.5 million under the cap. Cutting Brendel, McKivitz and Oliver saves an additional $7.4 million, dropping them to about $32 million under the number, and that's with Aiyuk's cap number still at $14.124 million.

In this scenario, the 49ers still need a couple of new offensive linemen, at least one or two new defensive backs and some help on the defensive line. Bringing back Young and/or Gregory to address the latter is a possibility, but they'll likely need to hit free agency and/or the draft for help on the O-line and in the secondary. If they don't re-sign Jennings, they'll have to find a wide receiver to replace him -- and they may need to find one to replace Aiyuk if they can't get him extended. That $32 million in cap room isn't going to be enough.

They could keep going down the veteran restructure list and get money out of the Armstead and Warner deals. But we're at the point now where we have to address some of the potentially difficult cut decisions.

Tough calls: Juszczyk has been in San Francisco for all seven of Kyle Shanahan's years as coach. He is a vital part of the 49ers' offense and surely would be missed. He also turns 33 in April and is scheduled to earn $6.25 million in salary and bonuses in each of the next two seasons. None of that money is guaranteed. Cutting him would save the team $4.911 million against its 2024 cap. If nothing else, it might need to go to Juszczyk and ask him to rework his deal. The relationship he has with Shanahan and the organization might make that easier to do than normal, but regardless, it's difficult to imagine Juszczyk returning to the 49ers on his current contract.

Then there's the matter of Greenlaw, which is especially challenging now in the wake of his Achilles injury in the Super Bowl. That injury makes it very unlikely he will be ready to open the 2024 season, and it's possible he ends up having to miss a significant portion of it. He is entering the final year of his contract and is scheduled to earn $8.7 million in salary and bonuses. None of that money is guaranteed, but if he's still on the roster on April 1, $2.5 million of it becomes guaranteed.

Perhaps not coincidentally, that $2.5 million is pretty close to the $2.1 million he'd make via CBA-mandated injury protection if the Niners released him and he was unable to pass a physical (which, by April 1, will surely still be the case). Releasing Greenlaw before April 1 would save the Niners $6.806 million in cap space. (The $2.1 million injury protection money would not hit their cap until after the season.)

As is the case with the Chiefs and Omenihu, this would be a cold and difficult decision, but it's there for the 49ers if they need it. Greenlaw, who doesn't turn 27 until May and has back-to-back 120-tackle seasons, would certainly be a candidate to return on a different deal or even do an extension that reflects his current health situation by reducing his 2024 compensation and floating money into future years. I don't want to be accused of writing "Niners should/will cut Greenlaw," but it must be pointed out that his deal offers them a chance for some easy cap savings that might not hurt them on the field in 2024.

OK, now let's back up to where we had the Niners $32 million under the cap, and for the sake of simplicity, let's say they outright cut Juszczyk and Greenlaw (even though it's more likely they find some other solution with both of those players). Now we have them at $43.717 million under the cap. Extending Aiyuk on a deal that delivers maximum 2024 savings puts them about $53 million under -- and their No. 1 offseason priority will be set. This is the ideal scenario, as it would enable them to address other needs at several positions (and reduce their urgency to address wide receiver).

The Aiyuk trade scenario: Now, if the 49ers can't reach an agreement with Aiyuk on an extension and end up having to trade him, they would save the full $14.124 million of his 2024 salary. In our ongoing example, that would put them nearly $58 million under the cap and likely arm them with an additional high draft pick (maybe even a first- or second-rounder) from such a trade. Aiyuk would surely be missed, but with all of the massive cap numbers the Niners are projecting for their veterans in 2024 and in future years, at some point they're going to need to move on from some of their stars. If they can get a first-rounder back in an Aiyuk trade and use it to replace him at wide receiver, that might actually be the best way to go.

Having Purdy as cheap as he is for now would enable San Francisco to pay two receivers -- Samuel and Aiyuk -- at top-of-market prices. But few teams have done that successfully. And when you factor in the Niners' top-of-market spends at edge rusher (Nick Bosa), offensive line (Williams), tight end (George Kittle), running back (Christian McCaffrey), linebacker (Warner), defensive tackle (Armstead, Javon Hargrave) and cornerback (Ward), the roster gets extremely top-heavy.

The Niners are in a unique position. They're clearly operating toward the back end of a win-now window, with a team that has been to three straight NFC Championship Games and just lost the Super Bowl by three points in overtime. Worrying too much about their 2025, 2026 and 2027 cap situations could cost them a chance to run it back with a team that's clearly good enough to win it all. So maybe the 49ers do whatever it takes to keep Aiyuk and worry about the consequences later. Maybe the 2025 offseason, when they have to talk about a Purdy extension, is when their painful cuts start to take place. And maybe they win next year's Super Bowl, some of their older vets retire and they spin happily forward into a transition phase.

But I think the Aiyuk situation, given the way the rest of the wide receiver market still hasn't shaken out, is going to be very difficult for the 49ers to navigate this offseason. They could use help at every offensive line position other than left tackle. They will need to replace older vets like Gipson and Ryan in the secondary. They probably have to do something about the linebacker position if Greenlaw isn't coming back for a while (or at all), too.

The most likely outcome: To me, the most likely way this shakes out is Aiyuk ends up getting traded to a team where he's the clear No. 1 wideout and where he can get the extension he wants, leaving the Niners to draft his replacement in the first round. That's the cleanest way for them to address all of their other needs. I see San Francisco extending Hufanga and coming to some sort of arrangements with Juszczyk and Greenlaw that keep them both around. That leaves the Niners to run it back with the same basic core, some upgrades in key spots and Aiyuk cheering them on from afar.