Trail Blazers trade Anfernee Simons to Boston Celtics for Jrue Holiday

According to an NBA insider who spoke to The Oregonian/Oregon Live, the Portland Trail Blazers traded Adrian Simons to the Boston Celtics for Jrue Holiday, ending Simons’ seven-year tenure with the team.

Shams Charania of ESPN broke the story first.

Officially, the trade cannot be finalized until July. On Wednesday night, the NBA draft gets underway. Although contracts cannot be signed until July 6, the free agency period begins on June 30.

The 26-year-old Simons struggled to adjust to becoming the starting point guard last season, averaging 19.3 points and 4.8 assists.

When Portland picked point guard Scoot Henderson with the third overall pick in the 2023 NBA Draft, it seemed as though his time with the Blazers was coming to an end.

Superstar Damian Lillard requested a trade as a result of that move. For Holiday, he was assigned to Milwaukee. Holiday was soon dealt to Boston by the Blazers in exchange for Brogdon, Robert Williams III, and selections.

In exchange for Simons and two second-round selections, Holiday, 35, is now rejoining the Blazers.

Breaking: According to sources who spoke to ESPN, the Boston Celtics dealt Jrue Holiday to the Portland Trail Blazers in exchange for Anfernee Simons and two second-round selections.twitter.com/2ycXQicGkT pictures

Holiday, a two-time All-Star and six-time All-Defensive player, would be a good fit at point guard with Henderson coming off the bench if the Blazers decide to retain him.

The Blazers, on the other hand, prefer to play quickly, which is Henderson’s style.

Since taking over in 2021, coach Chauncey Billups has worked to strengthen the defense. Holiday is thought to be among the NBA’s top defensive guards.

The Blazers might also start Henderson at point guard, switch to Holiday at shooting guard, and then bench Shaedon Sharpe.

During the previous season, Holiday shot 35.3% from three-point range and 44.3% from the field, averaging 11.1 points and 3.9 assists.

Holiday might eventually be dealt to a team that is as competitive as the one that acquired him in 2023 from the Blazers.

With the Celtics, who won the NBA championship in 2024 but lost this season after star Jayson Tatum hurt his Achilles tendon in Game 4 of an Eastern Conference playoffs loss to the New York Knicks, Simons goes from a losing position to a winning one.

With Derrick White and Sixth Man of the Year Payton Pritchard, the Celtics have a formidable backcourt even without Holiday.

Simons has one year left on his $27.7 million contract, but it’s unknown if he will start for the Celtics.

Holiday has a player option left and two years guaranteed. Next season, he will earn $32.4 million.

Simons had moments of brilliance with Portland, but he never really settled there.

Simons, who attended the IMG Academy in Florida, was chosen by former general manager Neil Olshey with the 24th pick in the 2018 draft. Simons was the last member of the Olshey era team still playing.

The 6-foot-3 guard only made five starts in 154 games over his first three seasons as a reserve.

Simons started 30 games in 2021–22 as a result of guard CJ McCollum and Lillard’s injury. In each game, he averaged 17.3 points and 3.9 assists.

On March 23, 2025, in Portland, Oregon, Anfernee Simons #1 of the Portland Trail Blazers watches the first half of a game versus the Boston Celtics at the Moda Center. Rio Giancarlo/Getty Images took the picture.Getty Pictures

Near the 2022 trade deadline, general manager Joe Cronin—who succeeded Olshey after he was dismissed in December 2021—traded McCollum to the New Orleans Pelicans, in part to give Simons a path.

Simons averaged 23.4 points and 5.8 assists per game from January 3 (after Lillard’s season-ending core muscle surgery) until his season-ending injury on March 6.

That performance appeared to pave the way for Simons to play a big role in the team’s future.

However, he had some trouble starting beside Lillard the next season. Simons earned a starter position in 2023–24 after Lillard left, but he broke his thumb in the first game. Before an illness put him back, he played brilliantly for a few weeks after missing eighteen games.

In the end, Simons averaged 22.6 points each night while appearing in just 46 games.

Simons’ offense struggled last season as he tried to get used to becoming the team’s full-time point guard.

At the end of the season, Simons remarked, “It’s the toughest season I’ve had, just mentally.” I was just getting used to everything that was thrown at me.

In order to get open, he had to adjust to playing in a faster-paced system rather than the half-court setups he was accustomed to.

It might be challenging to transition after spending your first six years in the league playing a half-court offense, according to Simons. Because I discovered that the NBA game was played by running sets. For me, that was quite challenging. However, I believe I figured it out in the middle of the season.

Boston should make Simons feel completely at home. With 48.2 three-point attempts per game, the Celtics were the NBA’s top team. Portland came in at number 14 (37.7).

Simons may play both shooting guard and point guard for the Celtics, and he will be allowed to shoot threes in an offense that is perhaps more suited to his skill set.

He will also have an opportunity to win. Simons made it apparent that he was occasionally affected by losing during the Blazers’ rebuilding phase. Despite missing the playoffs the last four seasons, the Blazers qualified for the playoffs in his first three seasons.

On the trade front, the Blazers could only be getting started. In the event that the appropriate deals become available, the team would like to trade center Deandre Ayton and forward Jerami Grant.

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Aaron J. Fentress | afentress@Oregonian.com|@AaronJFentress (Facebook), @AaronFentress (Instagram), and @AaronJFentress (Twitter)

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