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Winners and Losers of the Damian Lillard-Holiday Shift

Oct 2, 2023; Milwaukee, WI, USA; Milwaukee Bucks forward Giannis Antetokounmpo (34) and guard Damian Lillard (0) pose for a picture during media day in Milwaukee. Mandatory Credit: Benny Sieu-USA TODAY Sports

DAfter months of speculation, Damian Lillard was finally traded. The move saw Lillard, Jrue Holiday and Deandre Ayton all experience changes of scenery, leaving the NBA landscape looking completely different. Holiday was immediately flipped from Portland to Boston, with the Trailblazers bolstering their haul from trading Lillard. 10 players and five draft assets were moved in less than a week, so who benefitted the most? Who is worse off after the trades? 

Winners and Losers of the Lillard-Holiday Shift 

Winner: Phoenix Suns 


Coming into the offseason, there was lots of speculation about this Suns roster. Sure, they had Devin Booker, Kevin Durant, Bradley Beal and Ayton, but what about their bench? There was also lingering discomfort around Ayton, mostly concerning his relationship with his star teammates.  

The Suns dominated free agency with their remaining money, picking up Yuta Watanabe, Bol Bol, Eric GordonandKieta Bates-Diop to solidify their bench unit. With nearly $130 million sunk into their big three, they made the most of free agency with what they could.  

With whisperings of Lillard to Milwaukee heating up, Phoenix saw its opportunity to jump in. Throwing Ayton into the trade talks in exchange for Jusuf Nurkic, Grayson Allen, Nassir Little and Keon Johnson. This group of four guys is a much better fit for the Suns, especially Nurkic.  

Nurkic is much more low maintenance, allowing the other three big starters to get their touches scoring the basketball. He won’t be complaining about his usage and showing no effort defensively. Allen gives the bench more shooting while Little and Johnson bring more athleticism. A great offseason has the Suns with one of the best rosters in the league.  

Loser: Miami Heat 

This one is the most obvious. For months, the Heat were the obvious target to land Damian Lillard, constantly negotiating with Portland. Pat Riley could not see eye-to-eye with Joe Cronin, with Tyler Herro likely being the deal breaker.  

Evidently, Portland traded Lillard Milwaukee for a lesser package than Miami would have ended up giving up. The Heat missed out on their star point guard while publicly throwing Herro and Kyle Lowry’s name into trade discussions, harming their relationship with both guards. While all seemed lost, Miami had one more chance.  

Portland’s intention was to immediately flip Holiday, and the Heat threw together an offer. Cronin, seemingly out of spite, again went in another direction, accepting Boston’s offer. Miami will again go into this season without a star running the offense despite their efforts to obtain Lillard. 

Loser: Robert Williams 

If you look at how everything shook out with those two trades, The Time Lord is definitely the biggest loser from last week. Williams went from being the starting center in Boston, the favorite to win the title, to being a backup to Deandre Ayton in Portland, a mid to lower tier team in the West.  

Even before acquiring Holiday, the Celtics have a loaded starting lineup. Williams has been in the Defensive Player of the Year discussion for a few years, and he’s an elite lob threat that provides rebounding as well. Boston swapped rim protection for wing defense, maybe believing Kristaps Porzingis can fill that hole.  

Instead of being in the chase for a ring next season, Williams will now compete with Ayton for minutes with the Trailblazers, a team looking to win years down the road.  

Loser, then Winner: Jrue Holiday 

On September 26th, Holiday expressed his desire to retire in Milwaukee, saying, “I don’t want to play for any other team.” A day later, The Bucks traded Holiday to Portland.  


He believed the Bucks could still do some great things with him on the roster and wanted to continue competing for championships. He went from that belief to being a member of the Portland Trailblazers, who finished 33-49 last season. 

Fortunately for Holiday, he and Lillard are both 33, so Holiday also did not match Portland’s new timeline. Knowing this, Cronin made it public he was available for trade and just a few days later, Holiday was moved to Boston. In a matter of days, Holiday went from title contender to the playoff bubble and back to title contender.  

Sure, Holiday may miss Milwaukee and feel betrayed by the organization, but if there’s any place he can exact his revenge, Boston is it.  

Winner, but you can’t tell: Damian Lillard 

Lillard made it clear after Portland drafted Scoot Henderson that he wanted to play for the Miami Heat. It seemed a foregone conclusion that the two sides would eventually agree to a package to send Lillard to his dream destination, but it never happened.  

Eventually, Damian Lillard reportedly had a conversation with Giannis Antetokounmpo about the two teaming up and days later, he was on his way to Milwaukee. Yes, Lillard wanted to go to Miami, but the Bucks give him a better chance to win a title.

Lillard has already gone through a welcome parade and media day in Milwaukee, and though his words express excitement, his face does not. Maybe it’s just his stoic demeanor, but Lillard doesn’t seem elated in his new situation.  

Winner: Boston Celtics 

Jrue Holiday is the perfect fit for Boston, especially after they moved on from Marcus Smart. When you look at their offseason as a whole, they virtually swapped Smart for Holiday and Williams for Porzingis. Holiday is a proven playoff performer and Porzingis is a highly skilled big. They cut some ties with beloved pieces, but the moves were necessary in order to reach the next level.  



From the looks of it, Brad Steven and the Celtics may not be done. They have an elite starting lineup and if they can round out their bench, Boston and Milwaukee could be on a collision course.  


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