Last summer, the Portland Trail Blazers traded Anfernee Simons for Jrue Holiday in a one-for-one swap with the Boston Celtics. Portland was wise to get ahead of Simons' expiring contract, capitalizing on Boston's financial crunch to come away with one of the best two-way guards in the league.
That decision looked even better for the Blazers in February, when the Celtics sent Simons and a second-round pick to the Chicago Bulls in exchange for Nikola Vucevic. It just further confirmed how little Simons was worth, given his contract situation and the declining value of his player archetype around the league. The fact that the Celtics were only able to turn Simons into an aging Vucevic made Portland's trade a huge win, considering Holiday remains the far more impactful player than Vucevic.
Celtics essentially got nothing for Anfernee Simons
That talent disparity was on full display in the postseason. While Holiday was giving the eventual Western Conference champion San Antonio Spurs a competitive first-round series, Vucevic was disappearing entirely from Joe Mazzulla's rotation.
Because of his lack of impact in Boston, Vucevic is now all but a lock to switch teams this offseason, NBA insider Marc Stein reported on The Stein Line.
Vucevic is set to hit free agency this summer and should still receive interest given the importance of stretch fives in the modern NBA. But comparing Vucevic's free agency interest to the trade interest the Blazers are expected to receive for Holiday, it's clear Portland got the better end of this situation.
The Blazers' front office was initially criticized for the Holiday trade. Though Simons was a trade candidate, many expected him to be shipped for future assets. General manager Joe Cronin took the opposite approach, acquiring an aging and expensive star.
Blazers continue to win the Jrue Holiday trade
But once Holiday took the court in Portland, the narrative quickly shifted.
This was just the latest of Cronin's initially polarizing bold trades to pay off. Holiday's first season in Portland and the underwhelming Simons trade return for Boston make this an increasingly lopsided trade in the Blazers' favor.
The development of Portland's youth and the return of Damian Lillard mean this franchise is ready to return to its winning ways. Holiday has proven throughout his career to be the two-way guard to help get teams over the top. Fortunately, he's now doing it in Portland, fitting a win-now timeline far better than most initially expected.
Boston may have strategically maneuvered a tricky financial situation to duck the apron, but with Vucevic walking, they suddenly have essentially nothing to show for trading away a star guard. Credit the Blazers front office for swooping in at the perfect time, because in just about any other situation, Holiday never would've been that cheap.
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