Why trading for Jrue Holiday just doesn’t make sense for the Boston Celtics

The surprise blockbuster deal sending Damian Lillard to the Milwaukee Bucks has created new unknowns for the Boston Celtics and the rest of the NBA. This move likely solidifies Milwaukee’s status as a top contender to come out of the Eastern Conference, but there are some other aftershocks from the move to sort out as well. Chief among them, what happens to veteran guard Jrue Holiday?

At the time of this writing, Holiday is a member of the Portland Trail Blazers. He and DeAndre Ayton were sent to the City of Roses as part of the broader three-team deal. It’s expected Portland will re-route the 33-year-old Holiday as the club enters a full youth movement. And Boston is one of several teams reportedly in the mix.

Jrue Holiday is a phenomenal two-way player and would be an impressive addition to the Celtics or any other team hoping to make a deep postseason run. Swinging a trade for Holiday may look like a home run for Boston in the abstract, but in reality, it seems both improbable and unwise, with a few key barriers getting in the way.

Barrier No. 1: Salary matching challenges

Holiday is set to earn $36.9 million in salary this season. As such, just making the trade work from a financial stand point alone would be difficult for Boston.

At a bare minimum, any would-be package for Holiday would need to include two of either Derrick White, Malcolm Brogdon, Al Horford, and Robert Williams III just to match salary. In some instances, a third or fourth Celtics player would need to be included as well.

Therein lies the problem for Boston. The Celts could make the math work, but it would cost the team in terms of depth. Already there are concerns that Boston’s rotation is a little thin. Sending out two featured role players for one very good player like Holiday would be quite a gamble.

Barrier No. 2: Competition in the trade market

Because the Celtics are reportedly exploring a Holiday trade, we have to assume team president Brad Stevens and company are at least curious about adding Holiday even with a hefty price tag. It takes two to tango, however, and it seems unlikely Boston’s best offer would be the most attractive to Portland.

Williams would probably need to be included for Boston to even keep Portland on the phone. Perhaps Payton Pritchard could sweeten the pot, but this seems insufficient. The Blazers have promising young guards in Scoot Henderson and Anfernee Simons. Likewise, Ayton figures to be the team’s featured big. Portland likely wants draft capital or blue-chip young players in any Holiday deal, and Boston’s best young players don’t quite make sense for the Blazers.

The Celtics do have all their own firsts and another from the Golden State Warriors, but even if this is the moment for Boston to cash in those assets, the Blazers are likely to field better trade packages from elsewhere in the NBA.

Barrier No. 3: Boston's future flexibility

Maybe Boston can indeed cobble together the right trade package without undermining the team’s competitiveness this season. And maybe Portland likes the Celtics’ offer enough to agree to a deal. It’s not impossible.

That said, trading for Holiday would put to bed any flexibility the Celtics have for the foreseeable future. The move would cost Boston many of its remaining trade chips, while also creating a notable financial log jam.

Holiday has a $39.4 million player option next season. If he opted into that deal, Boston would have north of $150 million in salary to just pay Holiday, Jayson Tatum, Jaylen Brown, and Kristaps Porzingis.

Winning is the ultimate goal, and if that quartet can deliver a championship, the price tag may be an afterthought. But trading for Holiday would paint Boston into a corner and leave only a few difficult pathways for hitting reset.

Final thoughts

Jrue Holiday is a tremendous player and he will elevate his new club’s ceiling wherever he lands next season. Even with concerns about depth, it may be a worthy risk for Boston to consider, however unlikely.

Regardless, the risks are paramount, and Boston is under no obligation to swing for the fences right now. The Celtics are poised to be serious contenders next year as constituted, with enough left in the cupboard to stretch that window for several seasons with the right moves.

A trade for Holiday would be a risky win-now play and an unnecessary one at that.

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Story originally appeared on Celtics Wire