As ESPN's Adrian Wojnarowski detailed on Tuesday, the situation in Portland is as tenuous as it has ever been during Damian Lillard's 10-year tenure with the Trail Blazers. The five-time All-Star has spent his entire NBA career in Portland, but one of the first questions facing a general manager to replace the recently fired Neil Olshey will be whether to give Lillard a big-money extension this offseason or to trade the superstar and rebuild around the return such a deal brings in.
With more than 100 free agents who signed this offseason becoming trade eligible next week, Portland's options in a trade are about to become more plentiful. A Lillard deal also could bring in the kind of draft haul that teams like Oklahoma City (for Paul George), New Orleans (for Jrue Holiday) and Houston (for James Harden) have been able to collect in recent years.
With that in mind, we asked our NBA experts to come up with potential moves the Blazers could make if the decision is made to end the Lillard era and start on a franchise reboot.
MORE: What lies ahead for the Blazers and Damian Lillard?
Portland takes on Boston's future
Portland gets:
Juancho Hernangomez
Al Horford
Aaron Nesmith
Payton Pritchard
Dennis Schroder
2022 first-round pick
2024 first-round pick
2026 first-round pick (top-10 protected 2026, top-4 protected 2027, unprotected 2028)
2028 first-round pick (top-4 protected 2028 if previous pick conveys in 2026; converts to 2028 second-round pick if not conveyed)
Boston gets:
Damian Lillard
CJ Elleby
Ben McLemore
Tony Snell
Cody Zeller
Kevin Pelton: Our colleague Zach Lowe suggested the Celtics as a destination for Lillard during our discussion on Tuesday's Lowe Post, and I'm running with that. Although finding a deal that makes sense financially between two teams currently in the tax is challenging, a large-scale swap like this -- which can't be completed until Dec. 15 because of the inclusion of several players signed as free agents this offseason -- would leave both in almost identical positions.
From Portland's standpoint, this deal makes the most sense as the start of a full-scale rebuild. Although the Blazers get a pair of 2020 first-round picks in Nesmith and Pritchard, the latter returning to his hometown after scoring 19 points in 18 minutes in Saturday's blowout win in Portland, the bulk of the value of this trade is in up to four first-round picks over the next seven years. At least one of those would come beyond the scope of Lillard's current contract.
Additionally, the Blazers would create huge cap flexibility to use in future moves. Horford's $26.5 million salary for 2022-23 is guaranteed for just $14.5 million, while Hernangomez's $7.5 million salary is fully non-guaranteed and Schroder's contract expires.
Dealing so many picks would be a huge risk for the Celtics, but Lillard would be the kind of playmaker they haven't had at point guard since Kyrie Irving's departure, and Lillard's long-term contract protects them from another star leaving in free agency.
This trade is already large enough, but I could see Boston preferring to expand it by sending Josh Richardson to the Blazers in exchange for Larry Nance Jr. That would help balance Boston's roster after sending out Horford while still remaining salary-neutral.
A deal with Philadelphia ... just not that one
Portland gets:
Tobias Harris
Tyrese Maxey
Matisse Thybulle
2022 first-round pick (top-10 protected)
Philadelphia gets:
Damian Lillard
Cody Zeller
Bobby Marks: No, that is not a typo. Yes, we're suggesting a trade in which the Blazers send Damian Lillard to Philadelphia and do not get All-Star Ben Simmons in return. Although Simmons is still only 25 years old and is one of the top defenders in the league (plus still has four years left on his contract), the goal for Portland should be to retool the roster and not launch a full-scale rebuild centered around Simmons.
The mechanics of this trade would see Portland take Lillard's $39.3 million salary and break it up into three quality starters who are on controllable contracts in Harris, Maxey and Thybulle. That would give Portland a quality young backcourt with Maxey, Thybulle and Norman Powell, allowing the Blazers to shift gears and also begin looking for a trade partner for CJ McCollum. The trade also would see Portland recoup a 2022 first-round pick that was lost to the Chicago Bulls in the Larry Nance Jr. trade this past offseason. The pick would be top-10 protected in 2022 and 2023 and turn into two second-round picks if not conveyed. From the 76ers' perspective, this is a push-your-chips-to-the-middle trade that does not involve multiple first-round picks but rather their depth. The goal following a move like this would be to find a trade partner for Simmons and replenish what was lost in the Lillard trade.
Fun times in Cleveland again?
Portland gets:
Collin Sexton
Isaac Okoro
Kevin Love
2022 first-round pick (from CLE)
2022 second-round pick (from HOU)
2024 first-round pick (from CLE)
Cleveland gets:
Damian Lillard
Robert Covington
Andre' Snellings: The Cavaliers have quietly built one of the more promising young teams in the league, and they were challenging for the lead in the Central Division before Sexton went down with a knee injury. Adding Lillard as the centerpiece of a backcourt featuring emerging star Darius Garland and versatile veteran Ricky Rubio then matching that with one of the best two-way frontcourts in the league including Covington, potential All-Star Jarrett Allen, Lauri Markkanen and Rookie of the Year candidate Evan Mobley would make Cleveland a force in the Eastern Conference as soon as this season. With all four starters around Lillard aged 24 or younger, the Cavaliers would still have the upside to continue to improve into legitimate championship contenders during Lillard's prime.
This would be one of the most talent-rich returns that the Blazers could hope to get for Lillard, and it would allow them to reload quickly with multiple valuable young players. Sexton, a lottery pick in 2018, came into his own last season when he averaged 24.3 points per game. Assuming Sexton returns healthy, the pending restricted free agent has the upside to be among the league leaders in scoring within the next few seasons. He is injured this season, but that would work for a Blazers squad that would be rebuilding for the future. Okoro was the No. 5 overall pick in the 2020 draft, and he has started to show signs of his potential to become the kind of rugged, physical, 3-and-D wing that has become a necessity in today's NBA.
Love is mainly in this deal for salary purposes, but the Blazers would have the space in the frontcourt to feature him and potentially raise his trade value in the penultimate season of his contract. This deal also would include two first-round picks, always valued commodities, plus a Rockets second-rounder that projects to be in that prized region at the top of the round where first-round talent can be acquired without the strictures of the rookie pay scale.
A Harden-esque deal from Minnesota
Portland gets:
D'Angelo Russell
Taurean Prince
2024 first-round pick (unprotected)
Rights to swap 2025 first-round picks (top-1 protected)
2026 first-round pick (top-3 protected, then becomes unprotected in 2027)
2028 first-round pick (two years after previous pick conveys, top-3 protected 2028, becomes unprotected 2029)
Minnesota gets:
Damian Lillard
Ben McLemore
Tim Bontemps: It's difficult to see a deal the magnitude of one involving Lillard happening in the middle of the season, with an interim general manager in charge of the Blazers. But if such a deal were to happen, a logical trade partner would be Minnesota, which also has an interim executive.
After making only one playoff appearance in the past 17 seasons, Minnesota has some real positive momentum this season behind Karl-Anthony Towns and Anthony Edwards. Adding Lillard to the mix could give Minnesota a chance to make a real push forward in the West -- especially given that Lillard is under contract for two more seasons after this one, plus holds a player option worth nearly $49 million for a third.
Portland, meanwhile, will get Russell in return. The former All-Star can help the Blazers attempt to stay in the playoff mix this season and is only signed through next year. Prince has an expiring contract, so the Blazers wouldn't be taking on significant future commitments. The obvious prize here, however, are the rights to four future first-round picks, three outright in 2024, 2026 and 2028 and swap rights in 2025. Much like the James Harden and Anthony Davis trades in recent years, this would be a bet by Portland that setting the picks as far into the future as possible would pay dividends.
Lillard goes to NorCal in a four-team deal
Portland gets:
Tyrese Haliburton
Davion Mitchell
Marvin Bagley III
Tristan Thompson
2023 first-round pick (from SAC)
Minnesota gets:
Buddy Hield
Cody Zeller
Sacramento gets:
Damian Lillard
Patrick Beverley
Tony Snell
Jaden McDaniels
2022 second-round pick (from MIN)
Oklahoma City gets:
Jake Layman
2022 second-round pick (from WSH, via MIN)
Kevin Arnovitz: When a franchise decides to move on from a player like Damian Lillard, there's virtually no way to extract present value in a deal. If Portland trades Lillard, it should look to Oklahoma City's transaction with the Clippers for Paul George. From whom can they recoup the most future assets? How can they position themselves best not for 2022 or 2023 but for 2024 or 2025?
A team like Sacramento has young players, future first-round picks and a desire to accelerate the team's timetable. (And a team like Minnesota has expiring deals that can make the money work; and the Thunder, bless their hearts, have the capacity to absorb a contract if incentivized with a pick.)
Portland, which presumably would look to move CJ McCollum for young prospects in the frontcourt, gets a young starting backcourt for the next eight years to replace the foundational one that served them for the past eight. The Blazers also pick up a first-round pick from the Kings. Sacramento gets a generational point guard in Lillard without surrendering De'Aaron Fox, and it adds a young forward in McDaniels from Minnesota, along with a second pick. For their trouble, the Wolves get Hield without having to surrender a first-round pick.