Playing out the Miami Heat’s Damian Lillard timeline

Oct 23, 2022; Los Angeles, California, USA; Portland Trail Blazers guard Damian Lillard (0) reacts after shooting a three-pointer against the Los Angeles Lakers with 12.4 seconds left in the fourth quarter at Arena. Mandatory Credit: Kiyoshi Mio-USA TODAY Sports
Oct 23, 2022; Los Angeles, California, USA; Portland Trail Blazers guard Damian Lillard (0) reacts after shooting a three-pointer against the Los Angeles Lakers with 12.4 seconds left in the fourth quarter at Arena. Mandatory Credit: Kiyoshi Mio-USA TODAY Sports /

Free agent negotiations across the NBA can begin today at 6 p.m. but, because the Miami Heat are limited to what they can offer outside free agents, they will have their eye on making a big acquisition via trade.

The Heat plan to wait patiently for Damian Lillard to make a final decision about his future. After meeting with Portland Trail Blazers decision-makers this week, Lillard has decided to give them a chance to improve the roster in free agency before potentially seeking a trade to a championship-caliber roster. If Lillard is to request a trade, it’s believed the Heat would be at the top of this list of preferred destinations.

But that might not happen for several weeks, if at all. This timeline complicates things a bit for the Heat, who must handle other business while keeping open an opportunity to trade for Lillard.

The Heat head into free agency facing a salary cap crunch. With $179 million already committed to 10 players, Miami is already above the salary cap and first luxury-tax apron of $172 million, and is very close to crossing the projected second tax apron at $182.5 million.

Miami’s own free agents include Gabe Vincent and Max Strus (who can both be re-signed with Bird rights), as well as Omer Yurtseven, Kevin Love, Cody Zeller, Jamal Cain and Orlando Robinson. Jaime Jaquez Jr., who the team selected with the 18th pick in last week’s draft, is slotted to make $3.5 million next season when he signs his rookie contract.

Beyond their own free agents, the Heat also have to make a decision on Kyle Lowry and Victor Oladipo. Both are set to earn a combined $39 million next season and Miami is motivated to move both contracts in order to create more space below the second apron. The Heat have until Sept. 1 to use the waive-and-stretch provision on either contract, which could create as much as $26 million in payroll savings and unlock the taxpayer mid-level exception worth $5 million.

However, waiving and stretching Lowry removes an expiring salary that could be used to complete a Lillard trade. Oladipo’s $9.5 million salary could also be used in a move.

So this is Miami’s dilemma: Wait for Lillard and watch rivals pick up valuable free agents, or move on and try to improve the roster on the margins.

There may be a way to do both. Here’s a hypothetical timeline that would allow the Heat to handle internal business and still be a player if Lillard seeks a trade.

June 30: Begin contract negotiations with Vincent. Stay in contact with Strus, who expects offers in the range of $12 million per season.

July 7: Sign Vincent using his Bird rights to a contract in the range of $33 million over three seasons.

Monitor Jerami Grant’s free agency. Grant heading back to Portland could extend Lillard’s decision, while losing him could be the final straw for Lillard. Also watch Draymond Green. League insiders expect Green to re-sign with the Warriors, which would take a valuable veteran off the table for Lillard and the Blazers.

Re-sign Love to a one-year deal worth $3.8 million.

Sign Dario Saric to a one-year, minimum contract with the promise of competing for the starting power forward spot.

Strus signs with another team for a contract in the range of $48 million over three years.

July 15: Haywood Highsmith’s $1.9 million salary for next season becomes fully guaranteed if the Heat do not waive him before this date.

July 7-17: Allow free agency to play out while awaiting Lillard’s decision. Ten days should be plenty of time for Lillard and the Blazers to sort out their business. Yes, the top free agents will likely come off the board, but the Heat aren’t in play for them anyway because they don’t have cap space. By holding onto Lowry’s salary, the Heat also won’t have the taxpayer mid-level exception available.

Mid-July-to-Aug: Sign outside free agents to minimum contracts. Targets at that price point could include: Damion Lee, Seth Curry, Jevon Carter, Cory Joseph, Jae Crowder, T.J. Warren, Juan Toscano-Anderson, Jeff Green, Taurean Prince and Wesley Matthews. Some of them will have agreed to terms by this point.

For this hypothetical exercise, let’s say the Heat sign Crowder (an option at power forward) and Matthews (to replace Strus).

Aug. 1: If still no decision by Lillard, begin actively shopping Lowry to create salary-cap relief. The Spurs and Clippers, if they strike out in free agency and on other deals, could potentially be trade partners. A Clippers deal could include Marcus Morris Sr. and Terence Mann, while the Spurs could absorb Lowry into their cap space and send back smaller contracts like Doug McDermott and Khem Birch.

Some time in August: The Blazers, having struck out on offseason targets like Green and O.G. Anunoby, cannot offer Lillard a chance to compete in the West. It’s tweeted by an NBA insider close to the situation that, Damian Lillard and the Trail Blazers have mutually agreed that parting ways is best for both sides moving forward. Blazers GM Joe Cronin will work closely with Lillard to send him to a team where the seven-time All-Star can compete for a championship and allows the Blazers to build around their promising young core.

August: The Heat trade Herro, Robinson/Lowry, Nikola Jovic, Jaime Jaquez Jr., first-round picks in 2028 and 2030, second-round picks in 2029 and 2030, and pick swaps in 2027 and 2029 for Lillard and Jusuf Nurkic.

The biggest issues with this hypothetical scenario is not being able to use the $5 million mid-level exception and the obvious risk of not getting Lillard at all. Either way, that exception likely isn’t getting the Heat a starting-caliber player this summer capable of tipping the scales next season. If the Heat don’t land Lillard, they can waive and stretch Lowry and Oladipo before Sept. 1 and still have that exception for the regular season. The Heat can trade Lowry or Duncan Robinson at any point in the summer and still have enough salary for a Lillard package.

Waiting for Lillard is somewhat limiting, but the risk is worth the potential reward.

Inside the Heat's decision between Lowry and Vincent. dark. Next