Boston Celtics Get Bad News About Jrue Holiday Trade

It turns out the Jrue Holiday-to-the-Portland Trail Blazers deal was not as lucrative as we all once thought.

The official trade was announced Monday, and although Holiday is going to Portland for guard Anfernee Simons, the Boston Celtics will not be receiving any draft capital back despite what was previously reported.

The Holiday trade was one of several reported moves the Celtics made to try and reduce their luxury-tax number after star swingman Jayson Tatum’s devastating Achilles injury.

Why Did The Celtics Not Get Draft Picks Back In The Jrue Holiday Trade?

The trade, which was broken by insiders in late June, initially had Holiday going to Portland for Simons and one second-round pick in both 2030 and 2031.

But even though Boston did get younger by acquiring the 26-year-old Simons, who has one year left on the four-year, $100 million contract he signed, it did not collect the draft picks after the Blazers reviewed Holiday’s medical records.

According to Oregon Live, there was nothing substantial enough to nix the trade, but whatever was ailing Holiday was enough to justify Portland removing the draft picks and making it a one-for-one swap of guards.

Holiday, who turned 35 on June 12, has not played in 70 games in a single season since 2017-18 with the New Orleans Pelicans. He averaged 30 minutes per game last season and played just 62 games while dealing with finger and hamstring ailments.

Simons averaged 19.3 points, 4.8 assists and 2.7 rebounds per game over 70 games for the Trail Blazers in 2023-24. In seven years with the Blazers, he has averaged 15 points, 3.3 assists and 2.7 rebounds while slashing .426/.363/.902 as a shooting guard.

Why Are The Boston Celtics Making So Many Trades?

Simons may not be in long for Boston either, since he could be flipped for more draft capital or a younger, less-expensive player — since the guard is on a valuable expiring contract.

With Tatum and his $54-plus-million salary out for at least the entire 2025-26 season after he tore his Achilles tendon in Game 4 of the Eastern Conference semifinals at Madison Square Garden, the Celtics will go from NBA championship favorites to Eastern Conference contenders.

That fact has required the Celtics to make some difficult financial decisions, like trading Holiday to Portland and dealing Kristaps Porzingis to the Atlanta Hawks for Georges Niang, in another deal that was officially announced Monday.

According to Spotrac, the Celtics are still about $330,000 over the highly restrictive second apron of the NBA salary cap. If they remain over the threshold, which is about $207 million, the Cs will not be allowed to trade their 2032 first-round pick and will be barred from certain salary-cap exceptions.

Since Holiday was locked into a four-year contract that just took effect this season, and with Boston already over the second apron for 2026-27, off-loading him for an expiring contract and draft picks was deemed smart while it waited and see how Tatum recuperated from the injury.

But without the second-round picks, which are valuable trade chips, Boston could look to make further moves — either involving Simons, or potentially featuring 2024 NBA Finals MVP Jaylen Brown, who was the 10th-highest-paid player in basketball last season at $49.2 million.