The Orlando Magic have seemingly telegraphed one of the biggest decisions of their offseason.
In early March, a league source confirmed reports that the team had changed the trigger date to guarantee Jonathan Isaac’s contract for the 2027 season. It moved from playing 52 games to June 28.
Regardless of whether Isaac would have played that 53rd game — he injured his knee in his 52nd appearance — it seemed this decision to change that trigger date was a compromise. It enabled the Magic to keep playing Isaac while also deciding it was time to move on.
It is expected that the Magic will waive Isaac and that his nine-year tenure with the team will end.
The question remaining is whether the Magic can afford to let him walk.
The advantages are clear. Only $8 million of Isaac’s $14.5 million salary for the 2027 season is guaranteed. That is very real money. With the Magic in the tax, saving $6.5 million in salary is saving an additional $6.5 million in tax payments.
But the Magic also now find themselves in a tricky spot. They are trying to add and improve their roster with very little ability in free agency. They must engage in the trade market one way or the other to fill the holes in their depth chart, let alone improve their roster.
It begs a critical question: Can the Magic afford to let Isaac walk for nothing?
That question, of course, requires another team willing to take on Isaac’s contract — even if it is just the $8 million guaranteed in dead money. And the Magic do not have significant draft capital to attach to for the cost of taking on that money.
The reality may be that the Magic are not expecting to find a deal for Isaac before the June 28 deadline.
The reality, too, is that the players the Magic might get for Isaac may not be worth the extra tax expense. The team is not only mindful of its tax bill for the 2027 season, but also mindful of going too deep into the second apron after Anthony Black’s extension is finalized.
What is even out there with the biggest thing the Magic can offer is some cap and tax relief ahead of free agency?
Team seeking relief
The main benefit of a Jonathan Isaac trade is more about getting tax relief or getting further under the cap. The reality is that the reason there might not be a market to trade Jonathan Isaac or add key players is that few teams are seeking that significant cap relief.
Maybe that will change as teams really dig into their summer. Maybe there is a team considering a harder restart than anyone is anticipating. That could be a chance for the magic to take on a higher salary.
Essentially the Magic want to retain Isaac’s $15 million salary slot while offering teams the chance to shave $6.5 million in payroll for next year. That might be a small thing. But Orlando essentially wants to help teams get off a bad contract.
The best target on that front might be Malik Monk.
The Kings are oddly projected to be $1 million over the first apron next year. They are expected to be active to shed some of their bigger salaries — Domantas Sabonis, Zach LaVine and DeMar DeRozan — to get themselves under the tax.
As an exercise of pure salary dumping, the Magic could offer Isaac’s contract for Monk straight up. That is a workable trade under the rules.
The Kings may not need to save money that badly to accept it without getting something valuable in return. Maybe Monk is worth attaching only the Magic’s second-round pick. They could be a happy receptacle for a salary dump.
But this is how difficult that trade can be. Just because a trade works does not mean that it is one another team will accept.
Monk has been a longtime target for Magic fans. He is coming off a relatively down year, but would be the upper end of outcomes.
The more likely salary dump scheme would be to try to wriggle Isaiah Joe or Aaron Wiggins from the Oklahoma City Thunder.
The Thunder are projected to be $28.5 million over the second apron with team options to pick up for Isaiah Hartenstein, Luguentz Dort and Kenrich Williams on team options.
Trading Isaac for Joe would save the Thunder only about $3 million next year after cutting Isaac before the deadline. That is not a significant amount. But it is something. And the Thunder might be more motivated to just cut bait and save the cash ahead of the summer — especially with multiple first round picks incoming.
Joe is one of the best shooters in the league despite his lack of size. He would give the Magic a boost in that skill.
Something bigger?
The other question is whether the Orlando Magic would get involved in something bigger.
The Giannis Antetokounmpo trade is hanging over everything in the offseason. And the Magic’s best avenue to get anything done might be to jump into a multi-team trade.
That is the only way to make the cap math work — a byproduct of all the aprons is how necessary complicated multi-team trades might be.
The Magic have been tangentially rumored to be in for Giannis Antetokounmpo. But it seems more likely the Magic are hanging around to be a second team involved in that trade. Orlando cannot take on a significant salary, but more teams mean more players to make the cap math work.
From a basic standpoint, a Jonathan Isaac-for-Bobby Portis swap works. The Bucks could easily send Portis to Orlando and have Isaac redirected somewhere else to a team looking to cut some salary after acquiring Antetokounmpo’s massive salary.
Portis is a solid backup center and a good veteran that would help the Magic, giving them a spot starter and a high-level backup in the end. His championship experience with the Bucks would not hurt a young team either. Even if his play will likely begin to tail off — and he is not an above-the-rim shot blocker.
The only other deal that I could find that might make some sense is the Orlando Magic sending Jonathan Isaac to the Atlanta Hawks to take on Corey Kispert’s contract.
Kispert is owed $27 million in the next two years and has a team option in 2029. He would give the Magic a key shooter off their bench — not to mention a former college teammate of Jalen Suggs. But Kispert was out of the Hawks’ rotation last year and does not give much on defense.
Kispert would be useful for the Magic. But a bad contract the Magic would have to wear for at least two years.
Still, having that salary slot would be helpful for trades down the road. And that is something the Magic should consider.
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