The Boston Celtics swung the first of what could be many trades this offseason, sending veteran guard Jrue Holiday to the Portland Trail Blazers late Monday night. The move was made to help get Boston under the second apron, but Celtics president of basketball ops. Brad Stevens also brought back an extremely gifted offensive player in Anfernee Simons. 

Let's just get this out of the way: It stinks to see Holiday get shipped out of town because of the CBA. Holiday was only in Boston for two seasons but his impact was huge, whether he was knocking down clutch corner threes or stymieing opponents on defense. Without him, there is no 2024 Championship banner hanging in TD Garden. 

But moving him was a necessary evil to get Boston under the second apron and avoid not only a massive tax bill, but trade and free-agency restrictions in the future. Holiday is due to receive over $100 million over the next three seasons on the extension he signed with the C's in 2024, while Simons is on an expiring $27.7 million deal. The trade trims about $5 million off the books for Boston, with some more work to be done to get under the second apron.

The Celtics not only got a talented scorer in the deal (along with a pair of future second-round picks), but one who will be playing for a contract in 2025-26.

Simons, who is only 26, is an offensive gunner who averaged 20.7 points per game as a full-time starter over the last three seasons. The shooting guard averaged 19.3 points, 4.8 assists, and 2.7 rebounds for Portland last season over 70 games.

Simons has the ability to create his own shot off the dribble, but where he's really thrived is from downtown, which will be music to Joe Mazzulla's ears. Simons has knocked down 37.4 percent of his threes while attempting 8.8 per game over the last three years. He is a career 38.1 percent shooter from three-point land and knocked down over 200 threes in two of the last three seasons, including a career-high 215 makes in 2024-25.

While Simons won't fill the massive void left in Boston as Jayson Tatum recovers from his Achilles injury, he can certainly help pick up the scoring slack for the Celtics. 

However, he's not a very good defender and is often targeted by the opposition on that end of the floor. Tatum and Jaylen Brown did just that whenever the Celtics faced the Blazers. Boston will have to hide him on defense, or really push him to become a better defender going forward. 

With Simons is on an expiring deal, he'll be playing for a new contract with the Celtics. That is if the Celtics end up keeping him this summer. There's always a chance Stevens could flip Simons in a separate trade in what will likely be a busy, busy offseason for Boston. 

The Celtics only reduced their payroll by $4.7 million with the Holiday-Simons swap, so they remain about $18 million over the second apron at the moment. Stevens will have to continue to chip away at the payroll, with the Holiday deal the first domino to fall.

Kristaps Porzingis ($30.7 million in the last year of his contract) and Sam Hauser (who is starting his four-year, $45 million extension) are the most likely candidates to be moved in the near future. Trading away both should get Boston under the second apron -- depending on what Boston gets back -- and still give Stevens some wiggle room to sign a few free agents (Al Horford and Luke Kornet are unsigned this summer) and the team's draft picks.

While there is still work to be done, and trading away a championship contributor like Holiday stings, the Celtics were able to get a player who can help next season while shedding about $5 million off the books. Whether Simons becomes a piece of the present/future, is dealt away this summer, or allowed to walk in free agency at the end of the season, Stevens' first major trade of the offseason is a solid win for the Celtics.