Will Damian Lillard Request a Trade After Blazers Fail 'Urgency' Test?

Sean Highkin@highkinFeatured ColumnistAugust 12, 2021

Portland Trail Blazers guard Damian Lillard plays during the second half of an NBA basketball game, Wednesday, March 31, 2021, in Detroit. (AP Photo/Carlos Osorio)
Carlos Osorio/Associated Press

A whirlwind free agency has come and gone, and the Portland Trail Blazers look more or less the same as they did heading into August.

As team president Neil Olshey has been telegraphing for weeks, his big move has already been made: installing his hand-picked choice of Chauncey Billups to succeed longtime head coach Terry Stotts.

Other than that, it's business as usual. Norman Powell is back on a big new deal. There's no traction on any deal involving CJ McCollum, or even any sign that serious talks have been had. And all the while, the question of Damian Lillard's future with the franchise has lingered, only growing stronger as the offseason has dragged on.

Lillard has been off in Tokyo, where his focus was on helping the U.S. men's national team take home the Olympic gold medal. Now that that mission has been successfully completed, he can turn his attention fully to the moves—or lack thereof—Olshey has made in response to the team's fourth first-round exit in five seasons. His future, along with those of Ben Simmons in Philadelphia and Bradley Beal in Washington, is the focus of the NBA world at the moment.

During his time with the national team, Lillard publicly addressed his situation a few times. And while he's shot down various published reports that he's actively seeking a trade, the noncommittal nature of most of his comments has to make Blazers brass more uneasy than ever about his desire to stay in Portland.

A word Lillard has used often is "urgency." He wants Olshey to be aggressive and creative, and to take the steps to surround him with talent in the same way other teams have to keep their superstars happy and contending.

PORTLAND, OR - JANUARY 23: Portland Trail Blazers General Manager Neil Olshey talks with Damian Lillard #0 of the Portland Trail Blazers before the game against the Dallas Mavericks on January 23, 2020 at the Moda Center Arena in Portland, Oregon. NOTE TO
Sam Forencich/Getty Images

If Lillard, or anyone else, was hoping for a splash from Portland's front office this summer, the minimum signings of Cody Zeller, Ben McLemore and Tony Snell don't exactly qualify. By themselves, they're all fine rotation players and marginal bench upgrades—Olshey could have done a lot worse as bargain-shopping goes. But one of the disconnects between Lillard and the organization is Lillard's belief the Blazers' roster isn't in a place where they should be a bargain-shopping team. To him, Olshey should be thinking bigger.

"[I]f you look at our team as it is going into next season, I don't see how you can say, 'This is a championship team, we just need a new coach,'" Lillard said last month.

Olshey hasn't addressed the media since his disastrous press conference introducing Billups in late June. No one knows when he will again; it might not be until training camp that he talks next. When he does, he'll likely point out that he had very little flexibility to work with. That's one of the themes he usually falls back on, along with reminding everyone that no free agents want to play in a small market like Portland.

But in a summer full of complex sign-and-trade deals, the amount of cap space teams have on paper matters less than it ever has. The Chicago Bulls, to use just one example, began the summer operating over the cap and managed, through sign-and-trades, to add nearly $200 million in new money for significant roster upgrades.

Outside of McCollum, who is the logical candidate to be moved for upgrades but whom Olshey has, to this point, shown zero interest in trading, the Blazers have other salaries they could have moved. Robert Covington's $12.9 million, Jusuf Nurkic's $12 million and Derrick Jones Jr.'s $9.7 million—all expiring—are exactly the kind of reasonable deals for solid rotation players that Olshey could have used in sign-and-trades.

Moving any of those players could have helped bring back the kind of long-term upgrades that would make Lillard feel better about spending the rest of his prime in Portland. Powell, who Olshey re-signed for five years and $90 million, could also have been used to facilitate a sign-and-trade for a bigger star.

Specific players aside—there's no use dealing in hypothetical names they could have added after the fact—the point is that the opportunity was there for Olshey to do something beyond re-signing his third guard for big money, adding three minimum-salary backups and calling it a day. Certainly, Lillard has made it clear that he was hoping for bigger moves.

Lillard just wrapped up a month with an Olympic team that included Jrue Holiday and Khris Middleton, who flew to Tokyo straight from Milwaukee after helping the Bucks win their first title in 50 years. Holiday came over to the Bucks from New Orleans last offseason in a blockbuster trade involving several players and even more future picks and swaps, an all-in move to surround two-time MVP Giannis Antetokounmpo with a championship-caliber supporting cast.

SAITAMA, JAPAN - AUGUST 05: Kevin Durant #7, Damian Lillard #6 and Jrue Holiday #12 of Team United States look on against Team Australia during the second half of a Men's Basketball quarterfinals game on day thirteen of the Tokyo 2020 Olympic Games at Sai
Gregory Shamus/Getty Images

It's easy to look at the Holiday trade now as a slam-dunk, because the end result was a five-year supermax commitment from Antetokounmpo and a Bucks title. But there's a world in which Kevin Durant wears a half-size smaller shoe, his foot-on-the-line jump shot in the closing seconds of Game 7 is a three-pointer, and the Bucks lose to the Brooklyn Nets in the second round.

Even if it had shaken out that way, Bucks management at least took the swing to give themselves a chance. Lillard wants to see Olshey take a home-run swing like that, not just be content to hit singles and doubles like his recent trades for Covington and Powell.

Lillard has said for years, as recently as last month, that in an ideal world he would like to play his entire career in Portland. There's no reason to believe he wants to leave the city to get to a bigger market, as many stars in his situation do. His family—not just his fiancee and their three young children, but lots of extended family as well—have roots there now. And he saw Antetokounmpo beat the table after the Bucks' title about winning "the hard way." Lillard talks about that often.

But he also wants to win, and outside of a Western Conference Finals run in 2019 that ended in a four-game sweep at the hands of the Warriors, the Blazers have never been close.

Lillard doesn't have to win a title at any cost. An educated read of his words and actions over his career would suggest that if he wound up being Reggie Miller in Indiana—retiring ringless but making several deep playoff runs and at least being in the mix most years with a fighting chance to get there in the end—he could live with that. What he doesn't want to be is Kevin Garnett in Minnesota, a perennial MVP candidate whose teams were never serious contenders. And it's hard for him or anyone else to look at the Blazers in their current form and see their future as anything but that.

There's also no guarantee he'll win anywhere else. With four years left on his contract, he wouldn't have much leverage to determine where he got traded, but a few potential destinations have been rumored more than others. He could find himself traded to Philadelphia, where Joel Embiid's health is always a concern and the rest of the competition in the conference is much improved. He could wind up in New York, where they may have to give up too many talented young players to build a long-term winner around him—as was the case when they acquired Carmelo Anthony a decade ago.

There's no obvious situation for Lillard to walk into like James Harden moving to Brooklyn with Durant and Kyrie Irving already there. How will it look if he forces a trade in the name of winning a title and then doesn't get one?

These are all things Lillard will have to weigh in the coming weeks and months as he figures out whether to request a trade, and if he does, how strongly to force the issue. The smart money is on the status quo, which Olshey has been so adamant about maintaining, holding for another year. Lillard will give Billups a chance, and in all likelihood, this roster will finish about where the last several Blazers teams have—in the lower half of the Western Conference playoff picture, penciled in for a first-round exit.

It would be stunning if Lillard wasn't in Portland on opening night of the 2021-22 season, as he has said he expects to be. But it's equally unlikely, if things stay the way they are, that he'll still be there a year from now.


Sean Highkin covers the NBA for Bleacher Report. He is a graduate of the University of Oregon and lives in Portland. His work has been honored by the Pro Basketball Writers' Association. Follow him on Twitter, Instagram and in the B/R App.