Superstar point guard Damian Lillard is one of the best players in the NBA right now, even without a Finals appearance or an NBA championship on his resume. Lillard is fresh off a season averaging 28.8 PPG and 7.5 APG during the regular season, and 34.3 PPG and 10.2 APG in the playoffs. Lillard did everything he could to get the Portland Trail Blazers into the second round, but Nikola Jokic and the Denver Nuggets were too much.
Lillard is almost 31 years old and is starting to get antsy according to reports. He wants to win a championship right now and doesn't want to bask in mediocrity any longer. Unfortunately for Trail Blazers fans, Lillard is reportedly at odds with the front office and staff about the direction of the team. This has led to widespread fear in Portland that their franchise superstar is unsettled and has major doubts about whether he should remain loyal to his team. First of all, the highly publicized coaching search after the firing of Terry Stotts has resulted in a ton of backlash aimed at Lillard’s way. Secondly, Lillard is unsure about how Portland can build a title contender in a loaded Western Conference. The Trail Blazers have tried to build a contender around Lillard with talents such as CJ McCollum and Jusuf Nurkic, but it hasn't worked out on both ends of the floor. More specifically, Portland struggled to get defensive stops when they need to. Looking ahead to next season, Portland have some options to try to improve the roster further. The most valuable asset is McCollum, the second-leading scorer on the team.
McCollum averaged 23.1 PPG for Portland this season and will have many teams scrambling for his signature. But even if Portland trade McCollum, the likelihood the acquired player will be better than him or enough to build a contender is slim to none. In actuality, Portland should have traded McCollum a few years ago for some valuable first-round picks. If the pick turned into a young star, Portland could have had a chance at making a run for the Finals.
The only way for Lillard to win a championship right now is to force a trade to 3 destinations: Philadelphia, Miami, or Los Angeles. Multiple first-round exits has left Lillard frustrated with his team's progress and should consider requesting a trade to the 76ers, Heat, or Lakers this offseason.
Trade Package: Ben Simmons, Tyrese Maxey, Shake Milton, two future first-round picks for Damian Lillard
This trade could work out best for both the Portland Trail Blazers and Philadelphia 76ers. The criticism of Ben Simmons has been well known around the league because he doesn't have a jump shot or confidence in scoring the ball. When looking at the rest of Philadelphia's roster, Ben Simmons might not be the long-term answer. Damian Lillard could be the answer because a pairing of Joel Embiid and Lillard could be the best little-big duo since Shaquille O'Neal and Kobe Bryant.
For Portland, they can rebuild with Ben Simmons as their new cornerstone. The Trail Blazers are well aware that building a contender will be tough with only CJ McCollum as their most valuable trade piece, and Ben Simmons could be the best possible return for a superstar of Lillard's level. Damian Lillard has never played with a superstar big man before and Joel Embiid could take him to his first NBA Finals next year.
Trade Package: Tyler Herro, Kendrick Nunn (Sign and Trade), Duncan Robinson (Sign and Trade), KZ Okpala, Precious Achiuwa, Goran Dragic (Sign and Trade), a first-round pick, a second-round pick for Damian Lillard
The Miami Heat clearly needed a third star to pair with Jimmy Butler and Bam Adebayo. The Heat struggled all year long and were swept, rather embarrassingly, by Giannis Antetokounmpo and the Milwaukee Bucks in the first round. Victor Oladipo, their key acquisition of the season, missed the entire postseason and could be out for next season as well. Miami have believed in Tyler Herro and Duncan Robinson for good reason, but they must be sacrificed to get the roster to the next level.
Damian Lillard in Miami makes the Heat the best team in the Eastern Conference, slightly ahead of the Brooklyn Nets. Brooklyn have an incredible Big Three, but Miami gets it done on defense at the highest level. For Portland, Herro and Robinson could be the perfect rebuilding duo. In terms of having a shot at making his first NBA Finals, Lillard fits perfectly in Miami. He can dominate the offense while Butler and Adebayo do all the dirty work to make sure the team stays focused and ready on defense.
Los Angeles Lakers
Trade Package: Kentavious Caldwell-Pope, Talen Horton-Tucker, Alex Caruso, Kyle Kuzma, Montrezl Harrell, 2027 First-Round pick for Damian Lillard
By far the best chance for Damian Lillard to make the Finals is forming a Big Three with LeBron James and Anthony Davis. Lillard and Anthony Davis could be another version and recreation of Kobe Bryant and Shaquille O'Neal, while LeBron James is still the smartest player in the NBA. That trio makes the Lakers the best team in the West by a large margin, without the likes of Brooklyn to contend for the 1st seed if Lillard went to the East.
The Lakers were still the favorites to make the NBA Finals this year as the 7th seed, but an untimely injury to Anthony Davis halted their progress. If the Lakers had Lillard on the roster, there is no question the team would have made it past the first round this year. The Lakers have to sacrifice Horton-Tucker and a ton of depth, but they must win now with LeBron approaching 37 years old.
Damian Lillard can lead the Lakers with Anthony Davis in the future after LeBron's retirement and has the best possible chance to make the NBA Finals next year if Portland makes this trade.