Insiders Reveal Latest Buzz, Trade Scenarios for POR's Damian Lillard 'Crisis'

Eric Pincus@@EricPincusLA Lakers Lead WriterJuly 24, 2021

Portland Trail Blazers guard Damian Lillard holds the ball during the first half of Game 6 of an NBA basketball first-round playoff series Thursday, June 3, 2021, in Portland, Ore. (AP Photo/Craig Mitchelldyer)
Associated Press

Was it a false alarm or an early warning of what's to come?

Just over a week ago, Henry Abbott of True Hoop wrote, "A source close to [Damian] Lillard says that in the days to come, he plans to request a trade."

A public trade demand has yet to arrive, but executives around the league are closely monitoring the Portland Trail Blazers as the NBA edges closer to the draft and free agency.

"It sounds like he is not getting moved anytime soon," one Eastern Conference source told Bleacher Report. "From what I've heard, [Lillard is] going to give it a chance and then decide closer to the [trade] deadline."

That would give president of basketball operations Neil Olshey precious little time to turn his roster from a playoff disappointment into a contender (at least in the eyes of his star point guard).

"I'm not sure how Olshey is going to get that done," a former Western Conference executive said. "Everyone in the NBA knows [the Blazers] are up against it. No one is going to help Olshey solve the Lillard crisis."

Can the Blazers be fixed in short order? If not, what can the Blazers expect to get back for Lillard?


What Is Portland's Quick Fix?

Craig Mitchelldyer/Associated Press

The answer isn't in the draft. The Blazers don't have any picks after dealing their first-rounder (No. 23) to the Houston Rockets for Robert Covington. Young players are rarely "win-now" pieces.

Even if Portland could trade into the top of the draft for a prospect like Oklahoma State's Cade Cunningham, which is extremely unlikely, he would not turn the Blazers into a contender in year one.

The free-agent puzzle starts with Norman Powell, who will opt out of the final $11.6 million on his contract, per Chris Haynes of Yahoo Sports. Portland acquired him during the season, sending out one of their most productive young players in Gary Trent Jr.

Should he leave, the Blazers won't have the means to replace him—just the non-taxpayer mid-level exception at roughly $9.5 million (which would trigger a hard cap). Paying Powell would put the team near that hard cap, taking away the NTMLE for the $5.9 million taxpayer mid-level exception.

Will Powell want to return to the Blazers if he's worried about Lillard's future? Talk about leverage—Powell will likely demand a sizable raise to stay, probably in the $20 million range.

The draft is a bust, and free agency is limited, so the only apparent alternative to appease Lillard would be trading some of his current teammates.

"Any team dealing with the Blazers are going to put the screws to them," the former executive said. "Unless they blow the whole thing up, they're going to have a hard time."

Steve Dykes/Associated Press

CJ McCollum, the team's second-best player, would have several suitors. An obvious target would be Ben Simmons of the Philadelphia 76ers, another franchise that underperformed in the playoffs.

"I don't know if Simmons makes the Blazers better or a contender," a Western Conference executive said. "At least he gives them a new look. He could help as a big-time defender to a team that desperately needs it, but Dame would literally have no help offensively."

Should the Blazers view Simmons as the solution to the Lillard problem, good luck. Sixers executive Daryl Morey is more likely to target Lillard and isn't giving Olshey a life raft off his sinking ship.

Unfortunately for Portland, that may be the trend as he canvasses the league. Somewhere among the other 29 teams, Olshey may find a deal, but will it return enough talent to not only replace McCollum but also improve the team significantly?

The Blazers have other players to offer in trade, including Covington, Jusuf Nurkic (whose $12 million contract is only $4 million guaranteed), Derrick Jones Jr. ($9.7 million if he opts in; otherwise, he's yet another free agent to consider re-signing), Anfernee Simons, Nassir Little and CJ Elleby.

A Powell sign-and-trade is a possibility, but given he'll be an unrestricted free agent after he opts out, the guard is not beholden to help the Blazers on the way out.

Rolling the team back with minor tweaks might have been a realistic approach, but with Lillard believed to be unhappy, that may not be a viable path.

This is Olshey's challenge. If he can navigate this successfully, mark him down as the favorite for Executive of the Year.


Blow It Up?

Rick Bowmer/Associated Press

When your car goes into a skid, you're supposed to steer into that skid to level out.

Deal Lillard, McCollum, Nurkic and Covington. Let Powell go as a free agent. Get as many draft picks and prospects as possible. Rebuilding is a natural part of the NBA cycle.

"They did a lot of good things the last decade," the former Western Conference executive said. "It's time, but Olshey may be fighting for his job. His [position] may be tied to Lillard."

The Orlando Magic recognized they had reached a plateau and dealt Nikola Vucevic, Aaron Gordon and Evan Fournier before the deadline. The Oklahoma City Thunder moved on from Chris Paul, Steven Adams, Dennis Schroder and Danilo Gallinari.

Attempts to keep the Lillard dream alive may lead to short-term decisions that end with the same result. Now, ahead of the draft and free agency, is the time to turn the page.

In the Western Conference, the Golden State Warriors might be open to dealing James Wiseman, Andrew Wiggins, picks No. 7 and No. 14 in the draft and other considerations for Lillard. Wiggins, 26, may be expensive, but he is still young.

The Los Angeles Lakers only have the No. 22 pick, but if Olshey values guard Talen Horton-Tucker highly, he may be attainable for Lillard via sign-and-trade, along with Kyle Kuzma, Kentavious Caldwell-Pope and Montrezl Harrell (if he opts in). Portland could look to re-route the veterans to other destinations for additional compensation.

Would the Minnesota Timberwolves offer Anthony Edwards in a package for Lillard? How about Brandon Ingram from the New Orleans Pelicans? Would the Sacramento Kings part with one of De'Aaron Fox and Tyrese Haliburton? Or could something get done with Marvin Bagley III, Buddy Hield and the No. 9 pick?

The San Antonio Spurs have young talent to offer, including Derrick White, Dejounte Murray, Lonnie Walker IV, Devin Vassell, Keldon Johnson and the No. 12 pick. The Oklahoma City Thunder have the most enormous cache of draft picks the NBA has ever seen.

In the Eastern Conference, the Miami Heat don't have much to offer in draft picks. Still, Tyler Herro, Precious Achiuwa and KZ Okpala could be had (along with Goran Dragic and presumably Andre Iguodala to match salaries).

The Sixers can build a deal around Simmons (possibly to a third team with draft considerations to Portland) with Matisse Thybulle, Tyrese Maxey and No. 28. The New York Knicks have picks No. 19 and No. 21 and several young players (Obi Toppin, RJ Barrett, Immanuel Quickley, etc.). Would the Toronto Raptors have a viable package with the No. 4 pick, Chris Boucher and Malachi Flynn?

That's not to suggest the teams above would include all the listed assets to acquire Lillard, but that's a sizable menu of choices for Olshey to sort through. Couple that with trading away McCollum and the rest of the veterans, and the Blazers could be well on their way to starting over.

"New York and Golden State clearly have the best packages for Lillard," the Western Conference executive said. "Philadelphia in terms of draft considerations and young players, [assuming Simmons is re-routed]."

Naturally, Lillard will have some say in his destination. He may only want to go to a contender. With four years left on his contract (the final year a player option), how much leverage does he have?

If he doesn't have leverage, the Blazers will simply ignore a potential trade demand, but again, stars have shown they have considerable power. Anthony Davis was moved to the Lakers with one year left on his deal. James Harden was sent to the Brooklyn Nets with two. Lillard may get his way with three, assuming that's what he wants.

If Lillard is willing to play the villain to force his way to a short list of teams, the Blazers' options shrink considerably.

The draft is less than a week away. Free agency will soon follow, and the trade deadline projects to be in early February. Unless Olshey can find a way to make Lillard confident in the team's direction, the Blazers' future is in extreme limbo.


Email Eric Pincus at eric.pincus@gmail.com and follow him on Twitter, @EricPincus.