3 losers after Damian Lillard was traded to the Bucks

The nearly three-month-long Damian Lillard trade saga finally reached its conclusion on Wednesday. This came as Lillard was shockingly traded to the Milwaukee Bucks in a three-team deal involving the Phoenix Suns. Portland acquired veteran star guard Jrue Holiday, center Deandre Ayton, rookie forward Toumani Camara, Milwaukee’s 2029 unprotected pick and unprotected pick swap rights with Milwaukee in 2028 and 2030.

Meanwhile, Phoenix received veteran big man Jusuf Nurkic, shooting guard Grayson Allen, and forwards Nassir Little and Keon Johnson in the deal.

The Bucks were not even among the rumored trade suitors for Lillard. So, naturally, there is bound to be some disappointment among opposing teams who tried and failed to land the superstar point guard. Likewise, there is probably some disappointment among Milwaukee’s veterans who were re-routed to a rebuilding situation in Portland.

Here are three of the biggest losers following Damian Lillard's trade to Milwaukee:

Top 3 biggest losers following Damian Lillard's trade

Toronto Raptors star forward Pascal Siakam

#3. Toronto Raptors

Toronto Raptors star forward Pascal Siakam

Over the past week, the Toronto Raptors were heavily reported to be among the favorites to acquire Damian Lillard. After losing star point guard Fred VanVleet to Houston in free agency, Lillard was viewed as a major upgrade for Toronto’s point guard position. The move was also expected to elevate the Raptors out of mediocrity and help them potentially contend in the Eastern Conference.

It was rumored that Toronto’s best offer would be centered around two-way forward O.G. Anunoby and include young players, contract filler and draft compensation. However, in the end, the Raptors refused to include Anunoby in any offer, despite the Blazers’ interest, according to the Toronto Sun’s Ryan Wolstat:

“League sources mused Toronto simply would not dangle OG Anunoby for Lillard."

The 2022 Rookie of the Year Scottie Barnes and star forward Pascal Siakam were also not made available in trade negotiations. So, refusing to offer up Anunoby likely killed any potential deal as well as Toronto’s hopes to contend in 2024.

Instead, the Raptors now enter 2024 with a middling roster, no true superstar and veteran role player Dennis Schroder as their starting point guard. This makes Toronto easily one of the biggest losers of the Lillard to Milwaukee deal.

#2. Jrue Holiday

Former Milwaukee Bucks veteran star guard Jrue Holiday

Another one of the biggest losers of the Damian Lillard trade is Jrue Holiday. Earlier this week, Holiday’s interview with the Milwaukee Journal-Sentinel’s Jim Owczarski was published. During the interview, Holiday spoke about his desire to remain with the Bucks for the rest of his career:

“Before I even won here, I think I said I'm a Buck for life, and I mean that like deep in my heart.

“I don't want to play for any other team. I think we have a chance to continue to do great things as the Bucks team and organization, so I want to be in Milwaukee.”

The timing of the interview was quite brutal for the veteran guard as he was shipped to a rebuilding situation in Portland shortly after. This comes despite Holiday having already proven that he can be the starting point guard on a championship team in 2021.

However, according to ESPN’s Adrian Wojnarowski, Holiday is not expected to stay with the Blazers as Portland is already taking offers for the veteran:

“The Blazers remain engaged elsewhere on deals and will are expected to immediately engage contending teams on trade talks to move on Jrue Holiday, sources tell ESPN. Portland is committed to its young group of talented guards."

A trade to another contender should alleviate some of Holiday’s discontentment. However, considering that he expressed his desire to remain in Milwaukee for the rest of his career, Holiday remains a big loser in the Lillard trade regardless.

#1. Miami Heat

Miami Heat superstar forward Jimmy Butler

The unquestioned biggest loser of the Damian Lillard deal is the Miami Heat. The Heat were heavily attached to the superstar point guard since he requested a trade on July 1. Meanwhile, Lillard and his camp made it clear that he wanted to land in Miami all offseason. All of this led many fans to assume that a Lillard to Miami trade was inevitable.

To make matters worse, the Heat lost guards Gabe Vincent and Max Strus in free agency following their 2023 NBA Finals run. So, the team is quite thin in the backcourt, especially at the point guard position. Miami also sorely needed more offensive firepower after finishing just 25th in team offensive rating (112.3) and 27th in team 3-point percentage (34.4%) last season.

All of this likely would have made Lillard a near-perfect fit in Miami alongside stars Jimmy Butler and Bam Adebayo. However, the Heat weren’t able to get a deal done and instead let Lillard land with one of their playoff rivals in Milwaukee. The Miami Heat now look primed to take a potential step back in the 2023-24 season rather than a step forward.