When news of Damian Lillard’s trade to the Milwaukee Bucks hit Adrian Wojnarowski’s social media on Wednesday afternoon, there was a mad dash across NBA front offices to get into meetings and Zoom calls.
Not to discuss Lillard’s fit with Giannis Antetokounmpo, delicious of a topic as that might be, but because the three-team trade with the Portland Trail Blazers and Phoenix Suns opened a massive opportunity: 33-year-old All-Star guard Jrue Holiday might be on the open market.
Milwaukee’s pending superstar duo no doubt is the foundation of a potential championship team, but Holiday could end up playing an even bigger role as to who might win the title this season. This is one of the rarest transactions you see in the NBA: a league-altering trade that begets another possible league-altering trade.
The Trail Blazers just spent three months trying to squeeze together a deal for Lillard. It will be much easier to trade Holiday if, as is expected, they go forward with a youth movement and focus on assembling draft capital and move him onward.
That is not because Holiday is a “better” player than Lillard, who is one of the greatest offensive players of this generation. But because Holiday’s skill set — he’s a voracious defender coming off one of the best offensive seasons of his 14-year career — is so desired by contenders in the league. That he’s got championship experience and can play a variety of different roles only makes him more valuable on a star-laden team.
All of the teams that showed interest in Lillard could call the Blazers back to re-engage on Holiday. Plus many more.
• That would include the Miami Heat, who hadn’t been in touch with Portland formally in weeks, who could use Holiday in a variety of roles after losing guards Gabe Vincent and Max Strus this offseason. They still have the same young players, namely recent draft picks Nikola Jovic and Jaime Jaquez Jr., plus multiple future firsts they can use if Portland is willing to reconsider.
• Same for the Boston Celtics, who have been looking for a Malcolm Brogdon trade since June and have multiple first-round picks to offer for a player who could replace the defensive leadership of guard Marcus Smart. Holiday was a thorn in the Celtics’ side for years as a Buck and seeing him go West might be a relief, but what if they could acquire him themselves?
• For months, the Philadelphia 76ers have been embroiled in their James Harden mess and are facing stiff competition in the Eastern Conference. Making Harden an expiring contract and adding draft picks and potential far-out pick swaps could interest Portland, especially if they could then turn around and re-trade Harden to keep collecting draft assets.
• The LA Clippers nearly traded for Brogdon, had trade talks for Harden and kicked the tires on Lillard. The opportunity to add Holiday, a Los Angeles native, to their defensive-based perimeter has to appeal to them. They have multiple first-round picks and swaps deep into the future they could mortgage.
• The New Orleans Pelicans could pull off an outrageous move and use some of the assets they acquired for trading Holiday in 2020 (they still own two future Bucks first-round picks plus a swap from it) to try to get him back. They also have a selection of young players that could tempt Portland.
• The New York Knicks have been patient with all their draft assets for more than a year. They have eight tradeable first-round picks, plus a perfect contract to use in the expiring deal of Evan Fournier. New York is in a position to make two star-player trades if managed properly. Getting a possible Tom Thibodeau favorite in Holiday could be a big step in attracting another big star down the line, and provides a perfect backcourt mate for Jalen Brunson.
• The Sacramento Kings could reach another level if they were able to get Holiday and improve their 25th-ranked defense. They have three tradable first-round picks, plus some expiring contracts to offer. This is the type of deal the Kings, who are largely bringing back the same roster, could’ve been waiting for.
• Even the Golden State Warriors, who have interesting young players on their roster, plus a few far-out draft picks and swaps when Stephen Curry might be retired, could join the race. Provided they’d be willing to re-trade Chris Paul, who members of the organization have praised for his offseason work of trying to fit in. Curry’s never had a backcourt teammate such as Paul, but he’s also never had a teammate with Holiday’s skill set, and he’s five years younger.
Richard Jefferson says the Bucks have become his ‘”way-too-early favorite” with the addition of Damian Lillard.
If any of these teams find a way to make a deal with the Blazers, it could re-shift the title odds considerably. Holiday’s contract — he is in the final year of his deal and with this trade will not be allowed to extend until late March at the earliest — could make some teams nervous when it comes to getting into a bidding war.
Lillard going to the Bucks made them more offensively potent, a bigger television draw and worse defensively. Milwaukee was already a strong title favorite — and it just strengthened its position, jumping to the front of the line at Caesars Sportsbook.
Depending on what happens with Holiday, the Bucks could be immediately supplanted by their former point guard’s new team.
