Celtics Made a Confusing Decision on UCLA Alum Holiday

The NBA, like all professional sports, is a cold business.

Not even the longtime veterans are safe from it.

UCLA alum Jrue Holiday has been in the league for over 15 years, and he’s one of the league’s most consistent and valuable on-ball defenders. But as he’s gotten older, his contract has become a hefty trade piece.

Over his career, he’s collected many accolades such as becoming a two-time Olympic gold medalist, a two-time NBA champion, and a three-time member of the All-Defense Team.

So it wouldn’t be a surprise if Holiday finds himself in the Hall of Fame whenever his career is over. But currently, at the ripe age of 35, he’s still performing at a high level.

Although it’s not the level that he’s used to.

When he arrived in Boston to join the Celtics, they immediately locked him up to a four-year, $135 million contract extension, which would inevitably turn out to be a liability for the team.

The Celtics won the NBA Finals in 2024 with Holiday being a major part of that run as a defensive wizard.

But the magic in Beantown died down afterwards. The Celtics were one of the best teams in the league, securing the two-seed in the Eastern Conference and winning their first-round series against the Orlando Magic.

And then it happened.

Superstar combo guard Jayson Tatum ruptured his Achilles in the second round against the New York Knicks, effectively putting the Celtics’ future in question.

Holiday became the scapegoat once the season ended, and he was quickly at the center of trade discussions. In the end, he was dealt to the Portland Trail Blazers in exchange for Anfernee Simons.

But one of the deals that was offered to the Celtics could’ve been Boston’s Get Out of Jail Free card.

Turns out, the Toronto Raptors were heavily interested in Holiday in an attempt to secure a veteran who has won in this league.

Weeks later, it was revealed by NBA insider Jake Fischer that the Raptors made an offer that included the ninth overall pick in the Draft, but Boston ended up going with Portland’s offer instead.

The Raptors offered the Celtics the 9th pick in the NBA Draft for Jrue Holiday, per @JakeLFischer

The Celtics decided to take the Trailblazers offer instead

(Via @CelticsCLNS) pic.twitter.com/W8hgRnlG8e
— Fullcourtpass (@Fullcourtpass) July 17, 2025

Why would Boston do that? And why did it then start actively shopping Simons after the Celtics acquired him?

There’s a whole lot of questions to ask, especially since Simons is on an expiring contract. But if the goal for the Celtics is to get younger for when Tatum makes his return in 2027, wouldn’t the ninth overall pick at least inject some life into the franchise?

Celtics President Brad Stevens has made a lot of shrewd moves in his career, and it’s very possible that this could be another one.

But currently, there are still a lot of questions that need to be answered, in classic Stevens fashion.

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