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A New 4-team Damian Lillard Trade Where Everybody Wins – Bleacher Report
With the NBA draft, free agency, plenty of trades and the FIBA World Cup all over, we’re now in the quietest part of the offseason.
And although both of them made trade requests earlier this summer, Damian Lillard and James Harden remain with their respective 2022-23 squads.
Finding a logical-for-all-sides trade involving either is tricky, but in Lillard’s case, the Miami Heat are seemingly interested and in a position to give up a haul for a 33-year-old point guard who’s under contract through 2026-27 (when he has a $63.2 million player option).
The problem is that the Portland Trail Blazers must not love what Miami is currently offering. Otherwise, the deal would already be done.
To grease the skids, we’ve entered two more teams into the mix, moved some assets around and concocted a four-team deal that works for everyone.
As has become tradition with these four-team-trade articles, we need to present the entire deal in one snapshot.
Take it all in, and then scroll below for the explanations on why each team should be interested.
Portland Trail Blazers Receive: Kyle Lowry, Jonathan Isaac, Jalen Suggs, James Bouknight, Nikola Jović, a 2026 first-round pick from Charlotte, a 2027 first-round pick from Orlando, a 2028 first-round pick from Miami and a 2030 first-round pick from Miami
Portland Trail Blazers Lose: Damian Lillard, Keon Johnson and Anfernee Simons
Miami Heat Receive: Damian Lillard, Gordon Hayward and Chuma Okeke
Miami Heat Lose: Kyle Lowry, Nikola Jović, Tyler Herro, Duncan Robinson, Haywood Highsmith, a 2028 first-round pick and a 2030 first-round pick
Orlando Magic Receive: Tyler Herro, Duncan Robinson, Kai Jones and Keon Johnson
Orlando Magic Lose: Jonathan Isaac, Jalen Suggs, Chuma Okeke, Gary Harris and a 2027 first-round pick
Charlotte Hornets Receive: Anfernee Simons, Gary Harris and Haywood Highsmith
Charlotte Hornets Lose: James Bouknight, Gordon Hayward, Kai Jones and a 2026 first-round pick
As always, feel free to haggle over the prospects involved, the number of picks going one way or the other or any other tweaks around the edges.
But before you get too excited, read up on why this works for everyone.
Portland Trail Blazers Receive: Kyle Lowry, Jonathan Isaac, Jalen Suggs, James Bouknight, Nikola Jović, a 2026 first-round pick from Charlotte, a 2027 first-round pick from Orlando, a 2028 first-round pick from Miami and a 2030 first-round pick from Miami
Portland Trail Blazers Lose: Damian Lillard, Keon Johnson and Anfernee Simons
If the Blazers are going to grant Lillard’s trade request, a deal like this makes it more palatable than a two-team swap with just Portland and Miami.
By looping in Orlando and Charlotte, the Blazers increase their haul of draft picks and add at least one interesting young flyer in Jalen Suggs to go along with Miami’s Nikola Jović (or Jaime Jaquez Jr., depending on your preference).
In theory, the 24-year-old Simons is young enough to develop within Portland’s newly established timeline with Scoot Henderson, but those two would make up the kind of undersized backcourt that’s been an issue for the Blazers for most of the last decade.
Getting out from under his contract (which runs through 2025-26) and getting a first-rounder from Charlotte would potentially improve Portland’s long-term prospects.
The rest of this side of the deal is easy to explain.
Lowry’s contract expires after the 2023-24 season. He can mentor Henderson for a year, and then Portland can let him walk. Isaac’s contract is only partially guaranteed in 2023-24 until January, and it’s fully non-guaranteed in 2024-25. In essence, he’s on even more of an expiring contract than Lowry.
As for Suggs, Bouknight and Jović, they’re 22, 22 and 20, respectively. If even one of them hits as a potential long-term running mate with Henderson, that’s a win.
Once you include all of the picks, the Blazers would have one of the NBA’s best troves of assets, and it could get even better if they move Jerami Grant ahead of the trade deadline (although he can’t be moved until after December 15).
Miami Heat Receive: Damian Lillard, Gordon Hayward and Chuma Okeke
Miami Heat Lose: Kyle Lowry, Nikola Jović, Tyler Herro, Duncan Robinson, Haywood Highsmith, a 2028 first-round pick and a 2030 first-round pick
This is a lot to give up for a small-ish point guard in his mid-30s. By the end of Lillard’s current contract, his salary could be one of the NBA’s bigger burdens.
But Miami is probably the only team in the league that can justify gutting its stash of future assets like this.
Despite losing five players and only getting three back, the Heat would be left with an eight-man rotation that includes Lillard, Josh Richardson, Jimmy Butler, Hayward, Bam Adebayo, Caleb Martin, Kevin Love and Thomas Bryant. If Jaime Jaquez Jr. were NBA-ready right off the bat, even better.
That group’s title window might not be open for long, but it would be wide-open in 2023-24. Given Butler’s ability to drag two teams to the NBA Finals within the last four years, he’s earned a win-now move like this.
Lillard led the league in offensive estimated plus-minus last season. With the defensive attention he’d pull away from Butler and vice versa, Miami would suddenly have one of the NBA’s more dynamic attacks. Frontcourt playmaking from Adebayo and Hayward would help, too. And Richardson providing a little floor spacing is a nice bow on top of everything.
Orlando Magic Receive: Tyler Herro, Duncan Robinson, Kai Jones and Keon Johnson
Orlando Magic Lose: Jonathan Isaac, Jalen Suggs, Chuma Okeke, Gary Harris and a 2027 first-round pick
Orlando could easily justify standing pat and riding internal development. Paolo Banchero and Franz Wagner are both potential All-Stars, and the young Magic went 29-28 over their last 57 games of 2022-23.
But this trade would raise their short-term ceiling without sacrificing too much long-term potential.
All of Orlando’s most interesting young players—including Banchero, Wagner and Wendell Carter Jr.—would stick around and be joined by a combo guard in Herro who’s averaged 20.4 points, 4.1 assists and 2.8 threes while shooting 38.7 percent from deep over the last two seasons.
Plugging him into the rotation while losing Suggs and Harris would create some defensive shortcomings, but Orlando’s attack would be far more potent. The Magic could still play lineups with tons of length, thanks to Markelle Fultz, Wagner, Carter and Banchero.
Robinson is a nice bonus. Adding him alongside Joe Ingles would give the bench plenty of outside shooting to mix in with the starters.
While neither of Jones or Johnson may have the same upside as Suggs, they’re 22 and 21, respectively. There are still developmental possibilities for both.
Charlotte Hornets Receive: Anfernee Simons, Gary Harris and Haywood Highsmith
Charlotte Hornets Lose: James Bouknight, Gordon Hayward, Kai Jones and a 2026 first-round pick
One of the benefits of having a 6’7″ point guard like LaMelo Ball is that you can potentially get away with a smaller combo or shooting guard alongside him. That’s part of what’s made the pairing with Terry Rozier workable over the last three years, and Simons would almost certainly be an upgrade over that.
Beyond being two inches taller than Rozier and five years younger, Simons’ scoring average over the last two seasons (19.3) is comparable to Rozier’s (20.1), but his effective field-goal percentage is four percentage points higher.
A backcourt of him and Ball would be dynamic offensively, and Harris could spell either to increase the defensive upside and provide some three-point shooting.
Highsmith could earn some rotation minutes as well, but there’s also a chance he goes down as a throw-in in this deal. That’s fine, given the potential upside from Simons.
What Charlotte is losing to get Simons essentially comes down to the 2026 first-round pick. Neither Bouknight nor Jones has shown a ton of upside in this system. Hayward is an oft-injured 33-year old on an expiring contract who makes way more sense on a contender. He didn’t figure to be a part of the Ball- and Brandon Miller-led future anyway.
Simons has the potential to be worth giving up a first-rounder.
