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Blazers trade rumors: Jrue Holiday may incite ‘another league-altering’ deal

Andrew Hanlon
Andrew Hanlon

Rip City Project

Jrue Holiday, Milwaukee Bucks (Photo by Patrick McDermott/Getty Images)

The Milwaukee Bucks came out of nowhere to make a blockbuster deal with the Portland Trail Blazers, acquiring seven-time all-NBA point guard Damian Lillard. Included in the deal was Jrue Holiday, a critical piece to Milwaukee’s first NBA championship in half a century.

Holiday is not long for Portland, though, as the Blazers are ready to build their franchise around three young guards in Scoot Henderson, Shaedon Sharpe and Anfernee Simons.

From the Trail Blazers’ perspective, the centerpiece of the Lillard trade was then-Phoenix Suns center Deandre Ayton – now, however, it looks like a second centerpiece is emerging.

Portland Trail Blazers guard Jrue Holiday already triggering a bidding war

The NBA world was shaken by the Lillard trade, initially – and understandably – focusing on what the 33-year-old will bring to the Bucks and how he’ll fit alongside Giannis Antetokounmpo.

Meanwhile, Blazers fans were concentrated on Ayton, the 25-year-old former No. 1 pick who is now part of Portland’s young core.

It took a bit for everyone to dig into Holiday’s role in the deal. It seemed immediately obvious that he would be rerouted from Portland to a contender – but which one, and for how much?

As a bidding war for the two-time all-star guard ensued no more than 12 hours later, it turns out the answer to that second question could be “a lot.” A lot as in “another potential league-altering trade,” according to ESPN’s Brian Windhorst.

The NBA insider added that it will be much easier to trade Holiday than it was to deal Lillard because of his style of play and value to a title contender:

"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.ESPN’s Brian Windhorst on a Jrue Holiday trade"

Windy listed eight teams that could already be calling Blazers General Manager Joe Cronin to enquire about Holiday: The Miami Heat, Boston Celtics, Golden State Warriors, Sacramento Kings, Philadelphia 76ers, New York Knicks, New Orleans Pelicans and LA Clippers.

Cronin just proved he’s willing to wait things out in order to get the best possible return in a trade. If those aforementioned playoff teams want Holiday – who’s already proven he can put a team over the top and turn a contender into a champion – Portland’s GM can sit back and wait for them to one-up each other.

If that’s how things play out and the Blazers get a significant return for Holiday, it would put an entirely new spin on whether or not the Lillard trade was a success for Portland.

It’s fitting that Holiday was left in the background until everyone processed the rest of the trade – what it meant for Milwaukee, Phoenix, Portland, even what it meant for the Miami Heat. The five-time all-defensive team guard and was underrated, again; at least until everyone was reminded of how good he truly is.

Andrew Hanlon

Andrew Hanlon

Andrew is a Site Co-Expert for Pippen Ain't Easy. He earned a degree in Journalism from the University of Wisconsin-Oshkosh and began covering high school sports in 2014. He's covered the NBA since 2021, and his work has been featured on FanSided, SB Nation, Yahoo! Sports, Sportscasting, and GiveMeSport. He’s been in his PAE role since 2024 and previously held the Site Expert position for Rip City Project (Portland Trail Blazers). When he's not writing about, talking about, or watching sports, he can be found playing and coaching them with his five kids.