Everyone knew big moves were coming in Portland after the Trail Blazers bowed out early in the playoffs yet again. The only player considered untouchable was Damian Lillard. But after a messy head coaching search process, Lillard may end up asking out, as reported by Chris Haynes over at Yahoo! Sports.
We aren't at DEFCON 5 yet. Lillard hasn't officially asked for a trade. But the Haynes report can be viewed as a shot across the bow at the Blazers' front office, a warning that if they don't figure things out quickly, Lillard won't stick around. If he does do the unthinkable and request Portland find a new home for him, the Blazers won't have a lack of suitors. Here are four teams who both make sense as a landing spot and can offer an appropriate package for the superstar point guard.
The Celtics have been a popular name in hypothetical Lillard trade discussions because, like the Blazers, they underperformed severely in 2020-21. Boston needs a shakeup of some type and are entering a new era under rookie head coach Ime Udoka with a legitimate star of their own under contract in Jayson Tatum. If the last five years of basketball have taught us anything, it's that players of Tatum's caliber will not hesitate to force their way out if things aren't going well. The Celtics will avoid that possible future at all costs, and that includes looking into a Lillard trade.
They have an advantage over many other teams by virtue of having perhaps the most attractive trade piece in Jaylen Brown. Brown was a first-time All-Star this year and could expand his game even more with a larger role. But he alone wouldn't be enough for someone like Lillard. If Boston really wanted to get this deal done, they'd have to give up Brown, Marcus Smart, and a young player like Aaron Neismith or Payton Pritchard in addition to a few first-round picks. A high price, but that's what's required to get a player like Lillard. The Blazers can start over with a 24-year-old stud in Brown and good pieces to remain competitive. If new GM Brad Stevens is willing to pony up, this is one of the best deals the Blazers could get.
New York Knicks
Of course. The Knicks are relevant again and are a far more attractive destination for unhappy superstars now than one year ago at this time. They're loaded with cap space, which means they wouldn't have to exactly match Lillard's $39 million salary for 2021-22 in any possible trade. The downside for New York is that they'd have to give up nearly all the pieces that made the team exciting and playoff-worthy this season.
A package for Lillard would start with Julius Randle and RJ Barrett. They'd probably have to throw in one of Obi Toppin, Mitchell Robinson, or Immanuel Quickley, as well as two or three first-round picks. It wouldn't give Tom Thibodeau a ton to work with, but acquiring Lillard with cap space left over means the front office can overhaul the roster in free agency. It'll be a lot easier to convince free agents to come play at MSG with a certified superstar under contract for the next four years. To make this happen, the Knicks would essentially have to blow up their team. But the chance to get a guy like Lillard does not come very often, and the Knicks would have to think long and hard about it.
This would be a very Pat Riley move, and as such we cannot count the Heat out of these sweepstakes. Miami has an intriguing mix of young talent they could offer to Portland, i.e. Tyler Herro and Precious Achiuwa. They have all their picks. But that wouldn't be nearly enough to pry Lillard out of the Pacific Northwest. If the Blazers believe Victor Oladipo's brutal year can be chalked up to his injury issues, and if Oladipo would be willing to execute a sign-and-trade, then a package centered around those three could work. In that instance, Miami could salary match with Portland and be able to pull off the deal while offering a decent enough package.
Ultimately, though, this would likely come down to Riley's willingness to part with Bam Adebayo. Jimmy Butler is staying put, but Adebayo is young and has a max contract that's about to kick in. If Adebayo is on the table, the Blazers would probably take a deal of Adebayo, Herro, and a lot of first-round picks. Miami moves forward with Dame and Jimmy Buckets as their core with Achiuwa filling in for Adebayo and Duncan Robinson as the sharpshooter on the wing, since the Heat would definitely do whatever it took to keep him around if they made this happen. That's not an automatic championship contender, but it's the sort of big swing Riley has built his legacy upon over the years.
With all the Ben Simmons trade talk that has taken place since the Sixers went home for the summer, it's only natural they get included here. Simmons has his well-known flaws, but he's still an All-NBA defender who averages 7.7 assists per game for his career. Lillard paired with Joel Embiid is a walking contender for the Eastern Conference title every year they're together and legitimate championship contenders.
Theoretically, it's a deal that makes perfect sense for both sides. Simmons is probably the best building block Portland could get in return for their homegrown star. If the Sixers are willing to throw in Matisse Thybulle, Tyrese Maxey, and Seth Curry, this is a deal worth thinking about for the Blazers. It would be tough for Philly to give up two All-NBA defenders, a sharpshooter, and a good young player, but Lillard is Lillard. They'd do this without thinking twice. It puts a big bet on Embiid's health given the depth they'd be losing, but Daryl Morey is no stranger to such gambles.