Damian Lillard Finds New Home In Blockbuster Trade Proposal

Damian Lillard could be a great fit for the Houston Rockets if they make this mock trade with the Milwaukee Bucks.

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Credit: Troy Taormina-Imagn Images

The Houston Rockets are ready to take a giant leap forward in the West after a promising end to last season that saw them end with a 41-41 record. The team should improve with another year of continuity behind Ime Udoka as well as the natural progression of their young core of stars. However, the team needs a difference-making No. 1 option that can help them elevate into the Playoff conversation in the West.

The Milwaukee Bucks made a swing for Damian Lillard last summer and the move hasn’t worked out to everyone’s liking. With Lillard at the tail-end of his prime and his style of play not fitting as well next to the ball-dominant Giannis Antetokounmpo, the Bucks might have made a mistake by adding Lillard instead of the defensive-minded role-playing guards they had in the past.

To salvage the latter half of Giannis’ time with the Bucks, the franchise could make a deal with the Rockets which sets both squads on a new competitive journey.

Trade Details

Houston Rockets Receive: Damian Lillard, Pat Connaughton

Milwaukee Bucks Receive: Fred VanVleet, Reed Sheppard, 2028 First-Round Pick (HOU), 2030 First-Round Pick (HOU)

Both teams take steps in different directions but with moves that help them win. The Rockets add a leader who can carry them through offensive pitfalls while having the defensive setup around him to cover his deficiencies on that end. The Bucks add a low-maintenance guard like VanVleet on an expiring contract alongside adding a top-five pick like Reed Sheppard to start planning for the future.


The Rockets Establish Themselves As Threats In The West

The Rockets are betting on continuity and progression to help them be a Playoff team in the 2024-25 season after the forward steps the franchise took in Ime Udoka’s first season as coach. However, the West is arguably in one of the most talent-rich eras we’ve seen. The Rockets finished last season with 41 wins and the 11th seed, the best record for any 11th seed in NBA history. 

Given that the Memphis Grizzlies are expected to return to prominence and that none of last year’s playoff teams outside the Los Angeles Clippers have taken a step back this summer, the Rockets might still be a few years away from contention. But adding Damian Lillard right now could help the team exponentially from a competitive standpoint. 

He averaged 24.3 points, 4.4 rebounds, and 7.0 assists in a down debut year for the Bucks but might succeed in Houston with more complementary pieces around him.

Rockets owner Tillman Fertitta bragged about the franchise being the deepest team in the NBA, which might be true given the scale of young and veteran talent on their roster. This deal leads to them losing two guards and future picks but they add a Hall of Famer in return who is also an excellent leader. 

His impact on the franchise would be multi-fold. If a deal like this goes through, the Rockets would be in a great place to effortlessly replace Lillard with future additions or internal promotions. They maintain a lot of their acquired pick equity and give up two of their own picks for a period they project to be competitive, regardless of whether Lillard is on the franchise or not.


The Bucks Prepare Themselves For The Future

It’s hard to understate the dire asset situation the Milwaukee Bucks face at the moment. They have spent too many assets in recent seasons to remain competitive around Giannis Antetokounmpo. They were still recovering from the 2020 Jrue Holiday trade when they made the Lillard splash last season, eviscerating their cabinet of draft assets almost entirely. With Lillard’s fit being imperfect and the team’s aging core seemingly regressing, the Bucks need to course-correct before they can’t salvage their situation.

Giannis has given them a long-term commitment with a contract extension already, so the Bucks need to figure out the pieces around the Greek Freak. Fred VanVleet averaged 17.4 points and 8.1 assists last season, proving to be a winning influence on the Rockets. While his offensive production can fluctuate, he’s a tremendous floor-setter and a hard-nosed defender who would fit the Bucks style of play that works best with Giannis. 

Reed Sheppard averaged 12.5 points, 4.1 rebounds, and 4.5 assists in college, being tipped by many to be a Rookie of the Year contender this season. He would get a unique opportunity on the Bucks due to their dearth of guards and add a highly-valued skill such as shooting to the roster. 

Neither Fred nor Reed would need to be as reliant on playing with the ball to be impactful as Lillard, so they would be great fits on the Bucks even if it’s an overall talent downgrade.

Adding multiple first-round picks gives the Bucks a way forward to correcting other pieces of their roster like when they’ll eventually need a replacement for the 37-year-old Brook Lopez. This move also allows the Bucks to shed over $60 million in salary next season, a financial benefit that can’t be ignored by the second-apron team.


A Deal To Diversify Two Contenders

The Bucks wouldn’t look as appealing as title contenders by making this deal but they would be able to play a more sustainable style of basketball by adding the ideal role-players around Giannis. He averaged over 30 points on 61% from the field last season, one of the greatest seasons in NBA history. He had a usage rate of 32.8% to do that, which isn’t ideal for a ball-heavy player like Lillard. The fit of VanVleet and Sheppard might give the Bucks a better chance to contend than the one-dimensional Lillard.

Lillard’s offensive prowess is game-changing on its own, and the Rockets could use that. Jalen Green isn’t a consistent offensive player and there’s no other player who can be considered a high-volume scorer. Dillon Brooks, Jabari Smith Jr., Amen Thompson, Tari Eason, and more, are all defense-first players. Lillard would be the perfect conduit for the franchise, unlocking their offensive skills while knowing he’s covered defensively.

Alperen Sengun will have to readjust to the presence of Lillard, but the gifted center has shown malleability in terms of his role in the team’s offense. His post-playmaking should benefit Lillard rather than hamper him, so this trade could really shake the NBA up and add the Rockets to a crowded Western Conference race.

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Ishaan Bhattacharya is a content manager for Fadeaway World from New Delhi, India. With his expertise in NBA content creation, Ishaan brings a wealth of experience to his role, contributing to the site's authority and reach within the basketball community. Over the last year, Ishaan has interviewed Ray Allen and Mark Tatum, while also covering the 2023 NBA Abu Dhabi Games which saw the Dallas Mavericks take on the Minnesota Timberwolves.Since joining Fadeaway World in March 2022, Ishaan Bhattacharya has become known for his unique perspective on the NBA. He consistently delivers this insight through his daily news coverage and detailed opinion pieces on the most significant topics in the league.Before his tenure at Fadeaway World, Ishaan worked in corporate communications, where he serviced prominent sports brands, including NBA India, Sports18, Amazon Prime Sports, and Royal Challengers Bangalore. This experience in strategic communications for leading sports entities has enhanced his ability to craft impactful narratives and connect with a global audience.A true MFFLer (Mavs Fan for Life, for the uninitiated), Ishaan is a massive fan of the Dallas Mavericks. When he is not upset about Jalen Brunson walking in free agency, you can see Ishaan as an avid gamer and content creator. His passion for basketball extends beyond the Mavericks, as evidenced by his thoughtfully curated NBA Mount Rushmore, featuring LeBron James, Michael Jordan, Kareem Abdul-Jabbar, and Bill Russell—each representing distinct eras and bringing their unique qualities to the game.Featured On: ESPN, Sports Illustrated, Bleacher ReportYahoo Sports, NBA, Fox Sports, The Spun
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