The Portland Trail Blazers were believed to be painted into a corner when Damian Lillard finally issued a trade demand on July 1. Lillard told his club he only wanted to play for the Miami Heat. Portland was resolute to search for the best available offer, but Lillard’s willingness to play for a team other than the Heat was enough of a question to potentially tamp down the market.
Lillard’s desire to play in South Beach wasn’t the only thing deterring offers around the league. While the veteran guard was arguably coming off the best season of his Hall of Fame career with the Trail Blazers, acquiring him came with some real risk. At 33 years old, Lillard was a small guard with a reputation as one of the league’s worst defenders while on a massive contract that will pay him $58.5 million as a 35-year-old and $63.2 million as a 36-year-old in 2026-2027.
It took a specific type of team to want to push their chips in for Dame, namely one that was ready to compete for a championship immediately.
With Lillard applying pressure to be delivered to South Beach and only a limited number of teams that actually made sense as a trade partner, Blazers GM Joe Cronin had to get creative. He ended up taking a deal three-team no one could have seen coming, with a return that’s already so much greater than expected, and only getting better.
Damian Lillard is now a member of the Milwaukee Bucks. Jrue Holiday’s stay with the Trail Blazers only lasted four days before he was re-routed to the Boston Celtics. Portland’s haul for Lillard is very likely not complete yet, and it’s already undeniably impressive. Here’s a list of assets the Blazers got for Lillard so far:
- Milwaukee’s 2029 unprotected first round pick
- Boston’s 2029 unprotected first round pick
- Unprotected swap rights with Milwaukee in 2028
- Unprotected swap rights with Milwaukee in 2030
- Deandre Ayton
- Robert Williams III
- Malcolm Brogdon
- Golden State’s 2024 Warriors first round pick
- Toumani Camara
The initial Lillard deal roped in the Phoenix Suns with the Bucks, and allowed Portland to essentially swap Jusuf Nurkic and Nassir Little for Ayton. Just getting off of Nurkic’s contract is a nice piece of business for Cronin after the center was one year into a four-year, $70 million contract that immediately felt like an overpay.
Portland got younger, it got bigger, and it added some valuable future picks to its war chest in the Lillard deal. The haul probably isn’t done yet.
Brogdon is going to be traded. The 30-year-old guard has two years, $45 million remaining on his contract, and doesn’t make sense for a rebuilding team like Portland. It’s difficult to parse Brogdon’s value after injury concerns reportedly tanked a deal from Boston to the Clippers earlier in the offseason, but he should have a market with fringe contenders.
Williams could be moved, too. The big man is on a very team-friendly contract with three years and about $37 million remaining on his deal. At 6’10 with a 7’6 wingspan and explosive hops, Williams is a rim protector defensively and a major lob threat on offense. He makes sense as a vertical spacer for Portland’s new franchise player, Scoot Henderson, so he may remain with the franchise for this year. Still, the pairing between Williams and Ayton isn’t totally complementary with neither big having shooting ability, and there should be a major market for Williams’ services. It’s not impossible for the Blazers to add another first rounder for him eventually.
The Trail Blazers now have a clear direction moving forward. Henderson will be the face of the team at point guard. Shaedon Sharpe, last year’s lottery pick, offers size (6’6 with a 7-foot wingspan) size, shooting, and explosive athleticism on the wing. Ayton is a talented 7-footer getting the change of scenery he badly needed, and he’s locked up for the prime years of his career. The Blazers need more wings for their long-term build, but they have plenty of routes to add them.
The Blazers will likely be among the worst teams in the league this year. Alexandre Sarr should be at the top of their 2024 NBA Draft wish list as an athletic 7’1 big man with sky-high defensive potential who also has real offensive skill on the perimeter. Ron Holland, the G League Ignite wing currently positioned as the front-runner to go No. 1 in the 2024 draft, would also be a major addition for size, motor, defensive intensity, and ability to attack the basket.
Those future picks could be juicy, too. Milwaukee’s unprotected 2029 pick is a wonderful lottery ticket. The Bucks are loaded now, but their core outside of Giannis Antetokounmpo is aging and their future asset stash to replenish the team is now fully depleted. If Giannis ever leaves, that pick could be in the mix for No. 1 overall — and so could the pick swaps in 2028 and 2030. Boston’s unprotected 2029 pick feels slightly less enticing, but is still a nice asset moving forward that could hit big.
The Blazers are going to be bad this year, because Henderson is 19 years old and Sharpe is 20 years old. That shouldn’t deter people from being excited about their future, though. Portland now has a long runway to build its next contender with a great young guard and a high-upside wing already in-place. The future draft assets won’t convey until the end of the decade, but the Blazers can bank on adding premium talents with their own picks in the meantime.
The Heat’s best offer was never going to be compete with what the Blazers. By staying patient and true to his long-term vision, Cronin nailed the Lillard trade under difficult circumstances and set up his team for a better future.