Issues to be sorted out as Lillard tries to work way to Heat. What gives Miami flexibility

Damian Lillard has asked the Portland Trail Blazers to trade him to the Heat, and it would be surprising if the Blazers don’t work to accommodate him.

The starting point for Heat trade discussions seems simple enough: multiple first-round picks, and likely, Tyler Herro.

It’s everything else that could be trickier to navigate as Miami tries to land the seven-time All Star and Lillard tries to get to Miami.

Among the questions that must be sorted out between the Heat and Portland in trade negotiations:

▪ Do the Trail Blazers want Herro, who is beginning a four-year, $130 million extension next season, or will Miami and Portland need to find a third team to facilitate a trade?

Update: TNT’s Chris Haynes said a third team likely will needed to work out a trade.

The Blazers’ three best players, after Lillard, are arguably guards - Anfernee Simons, Shaedon Sharpe and third overall pick Scoot Henderson.

So Portland might prioritize finding a frontcourt player as a building block in its rebuild. And that could require a third team to become involved.

The Heat has the ability to facilitate a trade, from a cap standpoint, without sending back Herro, but it’s questionable if Portland would be content with merely receiving back draft picks and no frontline starter.

▪ Will the Blazers be insistent about acquiring Caleb Martin, who is entering the second-year of a team-friendly $20.6 million contract? The Heat prefers to keep Martin, according to a source.

Giving up Martin would be difficult for the Heat but ultimately might be necessary. He’s due to make $6.8 million next season but can opt out of the final year of his contract, which would pay him $7.1 million in 2024-25.

▪ Will Portland be adamant about acquiring both of the Heat’s two most recent first-round picks: forwards Nikola Jovic (selected 27th in 2022) or Jaime Jaquez Jr. (chosen 18th in last week’s draft)?

Though Jovic is entering his second season, Jazquez might be viewed as the player more likely to contribute this season after four seasons at UCLA. And that could make make Jovic more likely of the two to be included in a trade package, though the Blazers could ask for both.

Jaquez can be traded immediately. If he signs with Miami, he cannot be traded for 30 days.

▪ Will the teams be able to agree on the cap-facilitating competents of the trade?

Keep in mind that the Heat cannot take back more than 110 percent of Lillard’s $45.6 million salary next season.

Several permutations would work - including Herro and Duncan Robinson. The question is whether the Blazers would prefer to take Lowry’s expiring $29.7 million deal; Robinson’s contract (which has three years and $57 million remaining) or neither.

If the Blazers don’t want to be saddled with either contract, an offer built around Herro, Martin, Jovic, Jaquez and first-round picks and perhaps Haywood Highsmith would satisfy cap rules.

Keep in mind that the Heat can trade first-rounders in 2028 and 2030 but can trade a third first-round pick (in 2024) only if Oklahoma City agrees to take an unprotected 2026 first-round pick from Miami instead of a lottery protected 2025 pick (which is the current arrangement between the teams).

▪ Will the Blazers be insistent on the Heat taking the remaining three years and $54 million on center Jusuf Nurkic’s contract, or even the final four years and $27.9 million or Nassir Little’s contract?

The 7-foot Nurkic is still in his prime, at 28, but has appeared in only 8, 37, 36 and 52 games the past four seasons because of injuries and his mobility on defense is limited.

Nurkic, who is close friends with Lillard, has career averages of 12.3 points and 8.6 rebounds with the Denver Nuggets and Blazers.

In 52 games last season, Nurkic averaged 13.3 points and 9.1 rebounds while shooting 51.9 percent from the field, 36.1 percent on three pointers and 66.1 percent from the free-throw line.

Because Erik Spoelstra likes to play a stretch power forward (or center) alongside Adebayo, Nurkic’s improved three-point game is encouraging - if he ends up being traded to the Heat.

Before last season, Nurkic was 32 for 138 on three pointers in his career (23.2 percent). Last season, he was 43 for 119.

As for Little, he’s due $6.2 million, $6.8 million, $7.2 million and $7.7 million over the next four seasons, after averaging 6.6 points and shooting 36.7 percent on threes last season in 54 games and four starts.

The most ruthless request the Blazers could make, beyond asking for Bam Adebayo or Jimmy Butler (which would be a non-starter)?

If Portland insists on Herro, three first-round picks, Martin, Jovic and Jaquez for Lillard, Nurkic and Little. Lowry’s salary would be needed to facilitate that trade from a cap standpoint.

In that specific scenario, Miami would be sending out $69.6 million in salary and taking in $68.7 million. So Miami’s payroll next season would be about the same as its current roster, well above the $165 million luxury tax line.

The problem with that scenario would come in 2024-25, when the Heat would have $177 million committed to six players: Butler, Lillard, Adebayo, Jurkic, Little and Robinson. Even if Miami filled out its roster with nine players on minimum contracts, that would be a payroll of about $195 million, with a tax threshold projected to fall in the $172 million range and the second apron at $190 million.

So the Heat’s ability, in 12 months, to surround Lillard, Butler and Adebayo with players making more than the minimum would depend on A) whether Portland insists the Heat takes back Jurkic and to a lesser extent, Little and B) Whether the Heat can convince Portland to take back Robinson instead of either Lowry or neither player.

In a best case financial scenario, the Heat could acquire Lillard and have significant room under the luxury tax line to supplement its roster in 12 months.

Here’s how that could happen: If the Blazers take back Robinson as part of the deal, if they don’t insist on Miami taking Jurkic or Little, then the Heat would have as little as $139 million on its books and as much as $145 million if two among Kevin Love, Josh Richardson and Thomas Bryant opt in to the second year of their two-year deals. (It’s doubtful all three will opt in because of the relatively low salary numbers; perhaps only Love will).

That payroll number does not include Martin’s $7.1 million player option for 2024-25 because there’s a good chance he opts out next summer.

Either way, the Heat - in that scenario - would be in position to use a mid-level exception that could top $13 million next summer without crossing the tax line. But Miami can have that type of flexibility in a year only if the Heat can move off Robinson’s contract (in a Lillard trade or another way for expiring money), deal Herro in this trade and if the Blazers don’t insist on Miami taking back anyone but Lillard.

So depending on how a trade is structured, the Heat could be left with virtually no roster flexibility beyond minimum contracts - and a big tax - in 2024-25 and potentially beyond, or with the flexibility to add quality supporting pieces to a Butler, Adebayo, Lillard core, and more flexibility to re-sign Martin if he opts out in a year.

Either way, the Heat - with Lillard - would be in a far better spot than it is now. And that’s far closer to happening after Lillard asked Portland to trade him to Miami.