Boston Celtics trade away two-time NBA champion as rebuild begins after failing to defend title

The Boston Celtics have traded away a major piece of their 2024 championship-winning team as they continue to deal with the aftermath of losing star Jayson Tatum for the rest of the season.

Boston traded starting point guard Jrue Holiday to the Portland Trail Blazers in a late-night move just two days before the NBA Draft.

In exchange, the Trail Blazers sent back shooting guard Anfernee Simons and two second round picks.

It's something of a return for Holiday, who was sent to Portland by the Milwaukee Bucks in the Damian Lillard trade back in 2023.

Holiday never played for Portland, as Boston traded for the player and sent the Trail Blazers two first round picks in 2024 (which the Blazers used to draft Bub Carrington) and in 2029.

It wasn't immediately clear what year those two second round picks are from at the time of publishing. 

By moving Holiday, Boston loses a key defensive piece and a consistent facilitator who won an NBA title in Milwaukee in 2021 before helping the Celtics win a record-setting 18th championship in 2024.

But Boston also moves Holiday's contract off the books - which earned an average annual salary of roughly $37.6m per year and had an owed $72m in guaranteed money.

Holiday was 104th in the league in scoring (11.1 ppg) and 64th in assists (3.9 apg) last season.

Comparatively, Simons - the former 24th overall selection in the 2018 NBA Draft - was 36th in the league in scoring (19.3 ppg) and 41st in assists (4.8 ppg).

Moreover, Simons is on an expiring contract that earns only roughly $27.7m next season. He is eligible for an extension.

The 26-year-old Simons made history when he was drafted by becoming the first player selected out of high school since Amir Johnson in 2005. 

Simons played a post-graduate year at the IMG Academy in Florida, fulfilling the NBA's requirement of being one year removed from graduating high school before being draft eligible. 

He initially intended to attend the University of Louisville before a 2015 sex scandal and a 2017-18 corruption scandal under head coach Rick Pitino de-railed that commitment.

After starting out slow in his first three years in the NBA, Simons has averaged at least 17.3 points, 2.6 rebounds, and 3.9 assists across each of the last four seasons. 

The Celtics are looking to re-tool after losing superstar Tatum to an Achilles injury which will likely see him miss the entire regular season - if not also the playoffs.

Boston finished second in the Eastern Conference last season before being eliminated in six games by the New York Knicks.

Portland, on the other hand, missed out on the playoffs with a record of 36-46.