Exploring decisions on 3 of South Florida’s top-paid players: Howard, Butler and Bobrovsky

I can’t quite remember a time exactly like this in our sports history, when three of South Florida’s five highest-paid athletes have simultaneously arrived at a financial moment of truth, with looming decisions carrying significant weight for each of their franchises.

For the Heat, the decision is whether to give Jimmy Butler the full four-year max extension that he covets, a scenario that would pay him nearly $182 million over four years (2022-2023 to 2025-26).

For the Dolphins, the conundrum is whether to acquiesce to Xavien Howard’s demands to be the team’s highest-paid player, just one year into a five-year extension.

For the Panthers, the decision is what can be done with the final five years and $46 million of Sergei Bobrovsky’s contract, now that it’s clear that Spencer Knight is the team’s goaltender of the future.

Examining each:

HOWARD

▪ The decision: Each side has one, with the clock ticking toward the late-July start of training camp.

The Dolphins have been hesitant to rip up Howard’s five-year, $75.5 million deal (that was signed in May 2019) and give him the raise he covets. But they haven’t publicly ruled it out, even while remaining noncommittal with Howard for much of the offseason.

For Howard, the decision is twofold if the Dolphins don’t relent: 1) whether to sit out training camp and potentially beyond and 2) whether to demand a trade.

A source close to Howard, who turns 28 on Sunday, said he expects Howard to hold out at the start of training camp — if he hasn’t been given a raise by that point — but acknowledged it’s possible he could change his mind.

Two sources close to Howard say they expect an eventual trade request, with one noting that Howard has been “really upset” about the Dolphins doing new deals for other players but not him.

One associate said Howard was particularly annoyed after the Jason Sanders extension. This was nothing against Sanders - whom he respects - but, according to his friend, more a case of the Dolphins taking care of somebody else contractually before him.

If the Dolphins call his bluff, would Howard really sit out the entire season, costing him $12.1 million in base salary, coupled with heavy fines for not showing up? Unlikely. Perhaps, in that scenario, he would show up begrudgingly before the Sept. 12 opener against New England and be a malcontent employee until his contract expires or until the Dolphins move on, whichever comes first.

Howard’s agent, David Canter, is declining comment on the matter.

The Dolphins could avoid all of this by simply giving Howard an additional $8 million or so in new guaranteed money, which would allow him to jump Byron Jones in combined base salary/roster bonuses due over the next four years. Miami also likely would need to guarantee some of Howard’s 2022 salary, none of which is guaranteed.

Jones is due $55.3 million from 2021 through 2024, though only $20 million of that is guaranteed ($14 million in 2021, $6 million in 2022).

Howard is due $49 million from 2021 through 2024, though only $12.1 million of that is guaranteed (all in 2021).

What can’t happen from a Dolphins standpoint: A trade. Howard is too vital to the Dolphins’ defensive success to trade merely for draft picks.

Last October, after Howard conveyed that he would be open to a trade (but stopped short of asking for one), an NFL person who spoke with Dolphins management before the trade deadline said the Dolphins would only trade Howard if they could get a “Laremy Tunsil return” back — meaning two first-rounders and a player or two first-rounders and a No. 2.

Howard’s former agent wasn’t given permission to talk to other teams.

One person who speaks often with the Dolphins front office said it would surprise him if the Dolphins trade Howard. I don’t expect a trade. But a trade cannot be ruled out unless the Dolphins tell other teams — during a potential training camp holdout — that he’s not available.

If the Dolphins made that kind of trade in August, the draft picks wouldn’t be of any help in the 2021 season, obviously. And this regime wants to win immediately.

That said, this regime’s history (at least with Minkah Fitzpatrick and Kiko Alonso) has been to trade unhappy players even if Miami doesn’t appear to be getting equal value back. (The Alonso/Vince Biegel deal worked out fine for Miami.) But Howard is more important than either of those players.

The logical solution? I asked a former NFC general manager, and he said he would give Howard a modest pay boost — either with additional guarantees or a prorated signing bonus — because of his immense value to the Dolphins’ defense.

What about calling his bluff and seeing if he will come back before the regular season opener?

“I don’t know what that serves long-term,” said the former executive, who asked not to be identified because he’s still involved in the game. “He’s been a good player for a long time. He has a good argument to say he outperformed his contract. He’s one of the best corners in the game and you can make the case to reward somebody that you drafted and developed. I would try to avoid trading him.”

BUTLER

▪ The decision: The Heat has a big one, and Butler could have one, too, if the Heat’s decision isn’t to his liking.

What’s clear is Butler — who turns 32 in September — wants a max extension this offseason that would keep him in a Heat uniform through 36.

The four-year, $141 million contract that Butler signed to join the Heat during free agency in 2019 includes a guaranteed $36 million salary for next season and a $37.7 million player option in 2022-23. An extension would replace his 2022-23 option and begin that season.

A four-year max extension would include salaries of $40.5 million for 2022-23 (nearly a $3 million increase from the player option in Butler’s current contract), $43.8 million for 2023-24, $47 million for 2024-25 and $50.3 million for 2025-26.

A few things: 1) We’re told Pat Riley loves Butler and Heat ownership typically defers to Riley on personnel matters. 2) Butler fully expects to get the extension, from what we hear. 3) The Heat would like to keep him long-term, beyond this contract.

So I believe an extension is likely to happen. But what’s not yet clear is whether it will involve a fourth year or whether it will be at the full max in year four.

If Butler is extended four years at the max or close to it, the Heat likely won’t have the cap space to add a max player (without a sign and trade) for at least the next three offseasons and possibly five. Any third star would need to be added in a trade, potentially a sign-and-trade.

What happens if Butler doesn’t get the max extension? Only Butler and agent Bernie Lee know, and they’re not saying.

If the Heat doesn’t give the full max to Butler and he reacts angrily, a previously unthinkable scenario — trading Butler — could come into play.

I do not expect it to come to this, but if it did, there would be myriad possible options, including Butler perhaps in a deal involving Kyrie Irving or less likely, Damian Lilliard.

If the Heat traded him for a player with an expiring contract, Miami would have only $38.8 million in 2022-23 cap commitments, which is $76.2 million below the projected cap that season. That would be enough to sign a marquee summer of 2022 free agent using cap space (Bradley Beal, James Harden, Irving) and have significant space left over.

But here’s the problem with that: Harden, for example, had interest in Miami before the Nets deal because of Butler; without him, the Heat presumably would be far less appealing to him.

In this unlikely scenario of trading Butler and using his cap space on another star, Miami still wouldn’t have the cap space to add a third max player to replace everything Butler offers.

And as good as Bam Adebayo is, would a star believe joining a team with only three players under contract (Adebayo, Tyler Herro, Precious Achiuwa) presents an opportunity to win a championship? Unlikely.

Riley’s high regard for Butler leads me to strongly believe this will get resolved.

If the Heat gives Butler the extension at or close to the max, Miami needs to start rebuilding its draft assets, because that - combined with Herro and perhaps Duncan Robinson in a year or two — would be Miami’s only (attractive) means to acquire a third star to join Butler and Adebayo through at least the middle of the decade.

The upshot is that Miami would have two All Stars (Butler, Adebayo) under contract for five more years.

Incidentally, Adebayo and Byron Jones are the other two on the list of the five highest-paid South Florida athletes (with Butler, Howard and Bobrovsky).

BOBROVSKY

This one isn’t as impactful as the previous two but carries serious financial ramifications.

As it stands, Bobrovsky — who turns 33 in September — is due $46.5 million during the next five seasons, a combination of base salary and signing bonus that he hasn’t yet received.

That seven-year, $70 million contract, which is fully guaranteed, breaks down to $12 million in salary for him each of the next two seasons, then $10 million, then $6.5 million and then $6 million. He has a $10 million cap hit each of the five seasons.

He has the right to approve any trade through 2023-24 and can block a trade to 16 designated teams the following two seasons.

So what team could have interest hypothetically? Perhaps Arizona or Vancouver or San Jose, who have contracts they would like to move. Detroit or Buffalo could have interest, but it’s questionable if Bobrovsky would want to go there.

It would be easier to trade him after this coming season. In 12 months, he would have only four years and $34.5 million left on his contract, and if he plays well next season (in a 1/1A situation with Knight), the Panthers probably could trade him, especially if they offered to pick up some of the money remaining.

But the upshot to moving Bobrovsky in the next month would be this: Florida then could try to re-sign free agent Chris Driedger, who was fifth in the league in goals against average this past season at 2.07. (Bobrovsky was 39th at 2.91.)

A buyout for Bobrovsky, at this point, is unlikely. The Panthers have $9 million in cap space heading into the offseason.

What’s clear is this: Knight is the Panthers’ goalie of the future, and he will be cheap for the next 24 months. He’s due $925,000 each of the next two seasons before becoming a restricted free agent in July 2023.