Portland Trail Blazers: Should they regret not trading for Jrue Holiday?

After watching Jrue Holiday take his turn hoisting the Larry O’Brien Championship Trophy, the Portland Trail Blazers faithful may have felt a pang of regret knowing that he was made available last summer.

The All-Defensive guard was acquired by the Milwaukee Bucks to be the third option alongside Giannis Antetokounmpo and Khris Middleton. Although the fit was initially questioned, he turned out to be more than enough to get the Bucks over the hump.

What really cuts deep is how well Holiday would have covered for the Blazers weaknesses that were exposed by the Denver Nuggets in their first-round series—which ended in an early exit for Portland.

Jrue Holiday would have been a perfect fit for the Portland Trail Blazers

For one, Jrue is one of the few guards that actually has the defensive chops to survive playing out of position at the three. If the Blazers had traded for him and insisted on playing a three-guard lineup with him next to Damian Lillard and one of CJ McCollum, Norman Powell, or Gary Trent, the results defensively would have turned out much better than the lineup they ended up running out with Dame, CJ, and Norm.

Not only would he have supplied a significant defensive upgrade, he would have brought immense value on the other end of the court too.

Holiday has always been more than capable of pouring in points, off of the ball or creating for himself. He’s been tasked with being a top-two option on offense for the majority of his career, but it’s been made clear that his most fitting spot is as a third wheel when it comes to scoring.

With Giannis and Khris by his side, Jrue was able to find his spots and score when needed; allowing him to reserve his energy for locking down on defense and creating for others. He’d never been known for his passing, but he answered the bell on the brightest stages last season.

In the 2020-2021 playoffs, Holiday averaged 17.3 points and 8.7 assists per game, proving to be a natural complementary scorer and primary playmaker.

Against the Nuggets, it became evident that the Blazers have a severe lack of court vision outside of Damian Lillard. CJ, Norm, and others on the team are plenty capable of hitting open opportunities and creating for themselves, but Lillard was the only true floor general on the roster.

Having Jrue Holiday would have given the Blazers a perfect secondary playmaker and a backup floor general behind Dame.

Holiday’s presence as a perimeter defender and reliable source of offense would have made him a welcome addition on the Blazers roster.

Jrue Holiday, Damian Lillard, Portland Trail Blazers, Milwaukee Bucks

Jrue Holiday, Damian Lillard, Portland Trail Blazers, Milwaukee Bucks (Photo by Abbie Parr/Getty Images)

Would trading for Jrue Holiday have made the Portland Trail Blazers a contender?

There’s a danger with playing past hypotheticals in that many people expect everything else to remain the same, even if that one detail had been changed.

With the rest of the roster intact, and Holiday on the team instead of say, McCollum, the Blazers possibly could have been a true contender. That’s assuming that the rest of the moves that Portland made would have fallen in place as well though.

There’s no guarantee that the Blazers would have made a move for Norman Powell if they had Jrue Holiday already in tow.

Even with the rest of the roster in place and Jrue Holiday replacing McCollum, the Blazers would have been a dark-horse contender at best—even with the injuries that ravaged the rest of the playoff contestants.

The reason that Holiday worked so well in Milwaukee was because he wasn’t expected to be a top-two option on offense. In Portland, unless the team found a way to acquire him without moving McCollum, he would have been tasked with being the second-leading scorer behind Lillard. We know that that’s not a championship recipe from Holiday’s tenure playing alongside Anthony Davis.

The Portland Trail Blazers should not regret passing up on Jrue Holiday

While Jrue Holiday is an underrated, All-World talent, the Blazers shouldn’t have any qualms about not moving for him.

Holiday would not have made the Blazers a contender and the cost to acquire him would have further decimated the team’s future assets and ability to make more moves to advance the roster.

To acquire him, the Bucks gave up Eric Bledsoe, George Hill, three first-round picks, and two more potential pick swaps with New Orleans. Milwaukee had the depth and the roster in place to make that kind of all-in move for a player of Holiday’s caliber; the Blazers certainly did not.

If Portland had made a similar trade and acquired Holiday, they’d be in a worse position this offseason than they are now and it’s highly doubtful that they would have won it all like the Bucks just did.

Even though Holiday is probably the perfect co-star next to Damian Lillard, the Blazers should absolutely not regret passing up on him.