After losing in the first round of the playoffs for the fourth time in five seasons, Damian Lillard may want out of Portland. According to Chris Haynes of Yahoo Sports, this comes amid controversy over their head coach hiring process as well as concerns over whether the Blazers can build a championship contender around Lillard. The Trail Blazers are at a crossroads in terms of their viability to contend in the west and there are fair arguments in favor of rebuilding.

Lillard is set to turn 31-years-old and is under contract for four more years, arguably putting his trade value at its absolute peak. Every good team will be interested and the Blazers could extract a haul of draft picks and young players, like Oklahoma City got for Paul George and Houston got for James Harden.

If Lillard were made available this offseason, there are a handful of teams that could put together a respectable offer.

Teams worth mentioning

The Lakers and Jazz deserve a quick mention just over an old tweet by Lillard stating his interest in them should he move on from the Blazers. However, neither team has the blue-chip prospects nor future draft equity to make a compelling offer. The Clippers, Mavericks, and Nuggets (unless Michael Porter Jr. is offered) can also be added to this list.

Teams like Oklahoma City and New Orleans have enough draft capital to make a substantial offer for Lillard, but their timeline could disinterest him. The Thunder would have to push all their chips right now to acquire other stars for him to buy in. On the other hand, they might not want to take shortcuts in their rebuild for a 31-year-old All-Star. The Pelicans could cash most of their future picks for Lillard while keeping Brandon Ingram, but the pairing with him and Zion Williamson might not be enough to contend immediately in the West. They could also run into similar defensive issues as Portland had this past season.

Teams that could make somewhat of a compelling offer include Minnesota (Anthony Edwards, D’Angelo Russell, the draft rights to Leandro Bolmaro, up to four first-round picks), Chicago (Coby White, Patrick Williams, Lauri Markkanen via sign-and-trade, 2025 and 2027 first-round picks), and Charlotte (LaMelo Ball, multiple first-round picks). However, some of these teams run into the problem of not having enough talent to contend and could be better off holding onto and developing their young players.

Toronto has some very appealing young players in Pascal Siakam, Fred VanVleet, and OG Anunoby to offer for Lillard. They also have all their future first-round picks as well the 4th overall pick in this year’s draft to offer. Filling out a contender could be challenging afterward, but they certainly have the players and picks to make a very intriguing offer.

Miami has the foundation in Jimmy Butler and Bam Adebayo that should interest Lillard, but a trade package that includes Tyler Herro, Precious Achiuwa, and their 2025 and 2027 first-round picks could fall short. Including Duncan Robinson or Kendrick Nunn via sign-and-trade probably won’t thread the needle either.

New York is interesting. They could put together a very strong offer that includes RJ Barrett, Immanuel Quickley, Obi Toppin, Mitchell Robinson, and could include up to four of their own future first-round picks as well as an additional two they’re owed from Dallas. New York doesn’t need to match salaries for Lillard since they’re projected to generate close to $50 million in cap space this offseason. This could allow the Blazers to also create a massive trade exception. With Julius Randle being Lillard’s only potential All-Star teammate, he would have to have faith that the Knicks can build a contender around them. The Knicks should have plenty of flexibility leftover to find a third guy to pair with Lillard and Randle, but as you will see shortly, there are several teams that could put together offers just as strong but with rosters that could entice Lillard more.

Boston Celtics: Jaylen Brown and several young players and multiple first-round picks

Boston is a team that could make a serious offer for Lillard, but it would likely require Jaylen Brown. Ideally, they would like to keep him and try to offer everything else at their disposal to pair Lillard with Brown and Jayson Tatum. Pairing Lillard with the two of them should propel Boston back into the East’s elite.

However, an offer that includes every other asset they have could only get them so far. While a combination of Marcus Smart, Robert Williams, Romeo Langford, Aaron Nesmith, Payton Pritchard, Grant Williams, and up to four first-round picks could seem generous to some, it doesn’t guarantee a future All-Star level player for Portland. Also, given how young Tatum and Brown are, there’s also no guarantee that any of the first-round picks fall in the lottery, including ones in the late 2020s.

Boston’s pursuit of Lillard will likely come to down their inclusion of Brown, which, understandably so, is an extremely hard decision to make. With Brown’s inclusion, the Celtics might not need to add too much more beyond an additional prospect and a first-round pick or two. Still, Brown is just 24-years-old and is still improving. He may never be as great as Lillard but the longevity of Brown and Tatum could outweigh the smaller window of contention Lillard and Tatum would have. There is so much the Celtics can still do to build a contender around Brown and Tatum over the next few years.

Philadelphia 76ers: Ben Simmons, Tyrese Maxey, 2021 first-round pick, 2023 first-round pick, and a 2028 first-round pick.

Daryl Morey

The Philadelphia 76ers were the runner-ups in the James Harden sweepstakes with a trade package centered around Ben Simmons and future first-round picks. Ultimately Harden was traded to Brooklyn, his preferred destination. The Sixers can still offer that same trade package for Lillard, who can be just as dangerous next to Joel Embiid as Harden would’ve been.

One of the reasons Houston may have passed on Philadelphia’s offer for Harden was because of the incompatible timeline. The Rockets are currently in a rebuild and there’s no guarantee they’d be able to put a contender around Simmons by the time his contract runs up. If Portland were to acquire Simmons they may run into the same issue. It could make more sense to reroute Simmons to a third team and extract even more future picks and young players to help accelerate their rebuild.

Philadelphia has expressed their intent to help improve Simmons’ shooting but meetings have also taken place regarding his future there. Lillard is exactly the type of All-Star the Sixers would love to acquire for Simmons should both sides decide to mutually part ways. While the Sixers lose a considerable amount of defense going from Simmons to Lillard, the emergence of Matisse Thybulle could soften that impact and make trading Simmons an easier decision.

Golden State Warriors: Andrew Wiggins, James Wiseman, No. 7 and No. 14 picks in the 2021 draft, conditional 2026 first-round pick, and 2028 first-round pick.

Andrew Wiggins, Golden State Warriors

Lillard could have an interest in playing in his hometown and the Warriors can make a very strong offer for him. Golden State has come a long way from losing Kevin Durant in free agency to having the most trade assets among good teams. They managed to turn losing Durant into Andrew Wiggins and the 7th overall pick in the 2021 draft in the process.

Bottoming out the last few seasons has allowed the Warriors to select James Wiseman at No. 2 overall in 2020 and they’ll also have the 14th overall pick in this year’s draft to offer as well, and can offer multiple future firsts as well. The Warriors have been waiting for the next star player to become available so they can consolidate all these assets into one, and Lillard could be that player.

The ability to get as many as four first-round picks allows the Blazers to get a head start into their rebuild, especially with two of those picks being in the lottery this year. Also, getting the Warriors’ first-round picks in 2026 and 2028 gives the Blazers strong trade assets down the line. This Warriors core with Lillard realistically has around a five-year window for contention. By 2026 the Warriors should be on the decline, making those picks potentially very valuable.

Wiggins mainly acts as salary filler in this trade, though he could have some trade value for Portland with only two years left on his deal. The Blazers also get an opportunity to develop Wiseman, who still has a shot at becoming a very productive starting center. With Lillard’s contract outgoing in such a deal, the Blazers could potentially become a cap space team in 2023 once Wiggins’ contract expires.

If the Warriors offer the kitchen sink for Lillard, it’s going to be hard for the Blazers to decline. There could be pressure league-wide for Portland not to trade Lillard to Golden State. It’s already very difficult to provide adequate coverage on Stephen Curry and Lillard alone, who need just a slither of space to get what is considered a good shot for them. The two of them together, along with a healthy Klay Thompson as a tertiary lethal shooter, and Draymond Green facilitating and setting screens, feels like an unstoppable offense.

Note: The Warriors can only trade their 2028 first-round pick starting on August 2 once the 2021-22 league year starts. Also, the Warriors can only trade their 2026 first-round pick conditionally since it is currently tied up as a protection in the 2024 first-round pick owed to Memphis. Assuming the pick conveys in 2024 or 2025, the Warriors 2026 first-rounder can convey to Portland.