7 Damian Lillard Trades the Blazers Could Make

As it pertains to Damian Lillard’s future in Portland, I’ll believe the Blazers’ superstar truly wants out when I see it. But news out of the Pacific Northwest makes it sound like Lillard is more than a little frustrated with the direction of the only organization he’s ever played for. And suddenly, even shockingly, he could finally be ready to leave.

If you didn’t know by now, Lillard is incredibly loyal. He told Complex Sports in 2019, as he’s repeated numerous times over the years, that has wants to do it all in the city he’s grown to love. Adidas, his shoe sponsor and collaborator, has its North American headquarters outside Portland and he loves taking quick meetings with them. He doesn’t want to join a superteam. He wants to attract free agents to Portland. He wants to bring a title to Rip City. He wants to retire as the greatest Blazer of all time. Unfortunately—as the great philosopher and astute cultural observer from the North, Aubrey Drake Graham, once spent 3:49 rhyming about—you can’t have everything.

We all, of course, have breaking points and Lillard may have reached his and could be changing his tune after Chris Haynes of Yahoo! Sports reported over the weekend that the soon-to-be 31-year-old point guard, easily among the best in the NBA, has grown frustrated with recent team decisions and quite possibly Portland’s championship aspirations moving forward. He expressed on Twitter that Chauncey Billups, named the new coach of the Blazers Sunday, wasn’t one of the candidates he co-signed when the front office asked for input.

It goes without saying that if Lillard did decide to leave Portland and asked the Blazers to trade him, it would be a big deal—literally and figuratively. A six-time All-Star, Lillard just made his sixth All-NBA Team this past season and was part of the MVP discussion for stretches of the season. Still in his prime, Lillard is one of the best clutch shooters in the game, one of the few guys who can take over contests and will his squad to a victory by himself, and he authored one of the greatest individuals performances in recent playoff history with his 55-point effort against the Nuggets in Game 5 of their first-round series. If I have to sell you any harder on Lillard’s game you’re a lost cause.

The idea of attaching him to a serious contender—because chances are Lillard will have some kind of say in where he’s hypothetically traded and it ain’t going to be Detroit—is salivating for anyone who likes to play pretend GM. Which is every basketball fan. So I guess it’s our duty to cook up some trade proposals—again, we’re only sending him to contenders and not to Oklahoma City even though Sam Presti and the Thunder have enough draft capital to trade for Pope Francis. One week after we addressed the Ben Simmons trade speculation, it’s Dame’s time.

To keep it succinct, a ton. Superstars of his caliber don’t get traded often, but it obviously happens. And we have some recent examples to base our hypothetical trades on.

James Harden cost the Nets their future draft stock for what felt like a decade when he was dealt this past winter. In actuality, it was three future first-rounders plus four future first-round pick swaps and a couple of promising young players in Jarrett Allen and Caris LeVert in a complicated four-team deal that ultimately involved the Cavaliers and Pacers. Regardless, that’s a ton.

Anthony Davis cost the Lakers three good, young players in Brandon Ingram, Lonzo Ball, and Josh Hart plus three future first-round picks when AD went to Los Angeles during the summer of 2019. That’s a ton.

The package the Clippers gave up for Paul George isn’t the best example to use here since Los Angeles had to offer up the farm to get Playoff P from Oklahoma City knowing that securing him via trade would mean Kawhi Leonard would join him via free agency. Anyway, George cost the Clippers a stupefying amount of draft picks. That’s a ton.

Even Jrue Holiday, a very good guard with an awesome defensive resume, cost Milwaukee—four first-round picks (two swaps) for the services of the former Pelican and for getting someone to take the bloated contract of Eric Bledsoe off its hands when that multi-team deal went down this past November. That’s a ton.

Top 10 NBA players—Harden and AD clearly qualify—are going to cost you an astronomical sum. Lillard’s a top 10 player—we can argue about rankings another day—so expect the haul for him to at minimum cost a team multiple first-round selections and ideally a couple of attractive young players.

In terms of salary concerns for the team acquiring Lillard, while it’ll matter because math usually does when making trades in the NBA, teams will find a way to absorb his huge number and they can worry about those final two years of his deal down the road. Lillard signed a four-year max extension in 2019 and he’ll make $43, $47, $50, and $54 million a season over the next four campaigns. He’s signed until he’s 34. He’s been incredibly durable. He’s widely respected. He’s a vicious competitor. He never hides from a big moment. Whatever team trades for him would get its money’s worth.

Lillard, one assumes, would have a say in where he ends up going with all the cachet he’s built up with the Blazers organization that drafted him out of Weber State in 20212. But as we’ve seen over the years—paging JJ Redick, a different caliber player than Lillard, I know, but remember how the Pelicans did him dirty—what a team promises and what they deliver is often different. Speaking of the Pelicans, teaming Lillard up with Zion Williamson (at the expense of Ingram) would be intriguing and will be a popular hypothetical, but since we don’t think Lillard would relocate to New Orleans for a bunch of reasons we declined to cook up a Blazers-Pelicans trade.

Does Lillard prefer to stay on the West Coast—he’s a native of Oakland and his family is basically based in the Bay Area or up in Portland these days—or does he opt for someplace back East where getting to the NBA Finals might be a slightly easier task? Does Lillard want to team up with a specific big man (i.e. Joel Embiid) or does he have his eye on an organization known for stability and a winning culture (i.e. Miami Heat)? Once upon a time, Lillard said he’d love to play in Utah or Los Angeles if things didn’t work out in Portland. But that was ages ago in NBA life. Obviously, there are more questions than answers rights now. But if Lillard truly becomes available, a bunch of contenders will take their best shot.

As always, we’ll offer up this disclaimer that consummating NBA trades are way more difficult than assumed and we in the media tend to oversimplify the effort and packages. That being said, organizations across the NBA have been running all kinds of scenarios on their own trade machines following the news that Lillard may finally want out of Portland. Here’s our best shot at coming up with some realistic transactions that place Dame Time on a contender.

We’ll start off with a realistic spot: Philadelphia. The 76ers have a Ben Simmons problem, despite what GM Daryl Morey would have everyone believe, and while swapping Simmons for Lillard straight up wouldn’t cut it for obvious reasons, it’s a great starting point for our purposes. The 76ers need a point guard who isn’t afraid to shoot in the playoffs (Lillard checks the box) and the Blazers are going to need a point guard to replace theirs. As long as Dame is cool relocating to Philly this makes sense. Sixers fans won’t like having to throw in Tyrese Maxey and/or Matisse Thybulle plus picks. But for the combo of Lillard and Embiid, you bite the bullet. Philadelphia probably has to part with more picks than we threw in, but Lillard for Simmons, Maxey, and Tybulle is doable, especially since the Sixers are getting out from under that horrifically expensive max contract Simmons carries.

Since the Knicks are forever trying to find a competent point guard, expect to hear a lot of chatter about New York being a landing spot for Lillard. The Knicks are looking a whole lot more attractive these days after their surprising playoff appearance and with young players plus enough draft capital, New York could make a serious run at Lillard. The starting point would be RJ Barrett and throwing in a couple of other young players, like Mitchell Robinson and Immanuel Quickley. Knicks fans that grew to love the 2020-21 team filled with up-and-coming talent may cringe at losing a few of those names, but it’s worth it for Lillard. New York obviously has to throw in multiple future first-round picks, but since they have so much cap space they’re one of the easiest places to send Lillard. Lighting things up in the Garden on a nightly basis could be highly attractive for Lillard.

If the new president of basketball operations wants to get nuts, get nuts by trading Jaylen Brown and Marcus Smart. Brad Stevens already jettisoned Kemba Walker to Oklahoma City so the Celtics have a need at point guard heading into the offseason. While Boston has reportedly been reluctant to dangle Brown in various deals over the years, they might have to if pairing Lillard with Jayson Tatum is deemed too good to pass up. In our opinion, it would be. Celtics fans would probably hate giving up the rugged Smart, but it feels like he’s forever on the verge of finally being dealt and you absolutely give up Smart to get Dame. Boston might need to throw in more picks to Portland to make this happen, but here’s another hypothetical we think has some serious merit.

If you haven’t heard, Heat Culture is just different and considering Lillard’s desire to win I don’t doubt that he wouldn’t fit in perfectly with Miami. If the Heat is willing to give up some of its young talent, it’s totally doable considering the franchise will have cap space heading into free agency, especially if it doesn’t re-sign Victor Oladipo, the prudent move. Tyler Herro and/or Duncan Robinson have to be featured in this trade. So, too, does Precious Achiuwa, the impressive young forward Miami selected in last year’s draft. Andre Iguodala has a team option for ‘21-22. The Heat do not have a ton of draft capital to work with so that could possibly inhibit their pursuit of Lillard. But if Pat Riley wants him you know the Heat godfather will move heaven and earth to team Dame Time with Jimmy Butler and Bam Adebayo.

How much shooting do the Warriors really need? You can never have enough and while this trade might qualify as borderline far-fetched for a few reasons, you’ll hear plenty of people get giddy thinking about the possibility. And, quite frankly, it’s easy sending Dame Time to team up with the Splash Brothers and Draymond Green since Golden State has the Andrew Wiggins contract and that highly attractive picks (No. 7 via Minnesota and No. 14) in July’s loaded NBA Draft to offer up. Throw in a few more picks and a couple of other pieces (Kevon Looney and his player option for next season might not be ultimately realistic to include in a trade, but we threw him in here) and crazier things have happened in the NBA.

This one is best classified as far-fetched because I have a hard time believing Portland would deal Lillard within the division. But we’ll bite and cook up something featuring the Nuggets since they have the extremely attractive young scorer in Michael Porter Jr. to offer up as the centerpiece of a trade. Throwing in Aaron Gordon and his versatility can help make this happen. Imagine how much fun it would be watching Lillard-Nikola Jokic run the pick-and-roll.

The Mavericks would be selling low on Kristaps Porzingis. He did not have a particularly great campaign, he struggles to stay on the court, and there have been rumblings he’s frustrated in Dallas with his role. So in order to make this happen they have to throw in multiple picks plus super-sub Jalen Brunson. Pairing Lillard with Luka Doncic could be a little awkward since they are dominant ball-handlers. But hey, if Brooklyn can make it work with two walking buckets in the backcourt, why the hell can’t the Mavericks?