Less than 24 hours after telling Jim Owczarski of the Milwaukee Journal Sentinel that he wants to retire a Milwaukee Buck, point guard Jrue Holiday was traded to the Portland Trail Blazers along with a 2029 unprotected first round pick and two pick swaps in 2028 and 2030 for Damian Lillard. Finally, the Lillard saga ends and the Milwaukee Bucks come out the surprise winner for the seven time all-star.  

With the Portland Trail Blazers rebuilding, they will have the chance to send Holiday to a championship contender to get future draft capital that was lacking in this initial trade. At age 33, Holiday is a two-time all-star, being named as such as recently as last season. With three all-defensive first team’s on his resume, his impact on the defensive side of the ball can match his 19.3 points per game average just last season on any team.

Consolation Prize For the Miami Heat

Sure, he’s no Damian Lillard, but Jrue Holiday should be the next best player on Miami’s short list. He’d be a seamless fit next to Jimmy Butler and adds to an already stout defense with Bam Adebayo. As a Buck, Jrue Holiday has averaged 18.5 points, 6.8 assists, and shooting splits of 49/40/80% according to Statmuse, and that was his latest three seasons. He’s an all-defensive stud, NBA champion and could be the deciding factor in a close playoff series.

With Portland already in possession of DeAndre Ayton thanks to the 3-team Lillard trade, this could be how the Blazers land Tyler Herro while still getting more in return for Lillard. Even if Herro wasn’t included in the trade, Kyle Lowry’s expiring contract could prove useful as Lowry can serve as a locker room veteran for Scoot Henderson. Jaime Jaquez Jr. or Nikola Jovic could be enticing pieces to a rebuilding Portland squad. Miami could also try to get rid of Duncan Robinson’s monster contract, and Portland could see if he can shoot his way back to relevance.

Miami knows that they will need to retool quick since both the Celtics and Bucks got better this offseason and Miami’s biggest move was not resigning Max Strus.

Back To Where It All Started With The 76ers

The second biggest offseason story has been that of James Harden and the Philadelphia 76ers. With the feud between Harden and the ‘6ers getting worse by the day, this could be the opportunity to settle it.

Holiday was drafted 17th overall in the 2009 draft by Philadelphia, and they’d welcome him back with open arms, especially if it meant dealing Harden in the process. Holiday became the youngest all-star in franchise history in just his fourth season with the 76ers, and the only reason he was traded was to start Sam Hinkie’s “Process”.  Holiday was playing so well Lillard had to tweet about it back in 2013, and who knew that 10 years later, they would be traded for each other.

If jrue holiday isn’t a all star then I don’t know what is lol

— Damian Lillard (@Dame_Lillard) January 19, 2013

The Blazers presumably wouldn’t be interested in Harden, so they could involve a third team in this trade just like how they did to get Holiday. That way Harden can be sent to a team where he can contend and a contender could send draft capital to Portland in exchange.

Holiday could slot in perfectly next to Tyrese Maxey, and the defensive aptitude wouldn’t get turned down when he gets subbed out because the 76ers signed Patrick Beverly in the offseason. With P.J. Tucker and Mo Bamba next to the reigning MVP Joel Embiid, the 76ers could be a sneaky championship contender next to the giants of Milwaukee and Boston in the Eastern Conference.

Chicago Bulls Go All-In

A team that has been struggling at the point guard position is the Chicago Bulls. Point guard Lonzo Ball last played a basketball game on January 20, 2022, and as of June 2023, the team already don’t expect him to suit up for the 2023-24 season. Holiday could easily elevate the Bulls past their previous ranking of 24th offensively with his almost 20 points per game. He’ll keep their defensive engine going next to Alex Caruso as long as he isn’t included in the trade.

Holiday can provide Zach LaVine and DeMar Derozan backup on defense and give time for Nikola Vucevic to cover the paint on defense. The Bulls also have some young talent that could be tangled in front of Portland for their rebuild. The Blazers actually worked out Dalen Terry before the 2023 NBA draft, and could be interested in his services since they weren’t able to draft him that night. Coby White hasn’t turned into the scoring guard the Bulls wanted, and could use a change of scenery. Caruso’s age at 29 years old might be out of the initial timeline for Portland, but he could also help Henderson, Anfernee Simons and Shaedon Sharpe get an extra step or two.

If the Bulls want to make a splash in the East, especially with their aging all-stars, they’ll need to make a Holiday-sized splash in order to make any noise.

For More Wisconsin Sports:

Follow us @WiSportsHeroics. Also, check out our Merchandise Here! Get 20% off with the code “WSH.”  To read more of our articles and keep up to date on the latest in ALL of Wisconsin sports, click here! Green Bay Packers, Milwaukee Brewers, Milwaukee Bucks, Wisconsin Badgers.