The Boston Celtics have traded Jrue Holiday to the Portland Trail Blazers for Anfernee Simons and two second round picks. According to ESPN, the move saves Boston $40 million in luxury taxes and moves them within $18 million of the second apron. Simons is on an expiring contract worth $27.7 million this upcoming season. ESPN first reported the deal.
Karalis' analysis: This is a win for Brad Stevens and the Celtics for a number of reasons. First and foremost, it saves them some money, which has always been the goal. The $40 million in tax savings and moving them closer to the second apron line is the motivation behind all of this.
I see four possibilities with Simons:
- Flip him for someone cheaper
- Carry him into the season and move him at the deadline.
- Carry him into the season and let him walk as a free agent.
- Extend him and keep him long-term.
When I first laid out the path forward for Boston, I wrote:
"There are other expiring guys out there who can be moved. ... Unlike past offseasons, the goal isn’t to make a trade that makes Boston better. The goals are to save money and minimize how much worse the team gets.
If they can move Holiday, who was good this past season but nothing near his peak, and Porzingis, who was disappointingly unavailable at the most crucial moments to accomplish these goals in this manner, and get back somewhat useful expiring contracts, then that might minimize the future pain they have to endure to get under the tax."
Simons wasn't on my list, but he fits the bill. But at $27.7 million next season, there is still room to maneuver to save even more money.
The other thing I wrote in that piece was "The Celtics might have to play a sort of opposite paperclip trading game to get where they want to go. Instead of constantly trading small things for something incrementally bigger, they can trade a big contract for incrementally smaller deals."
Stevens can easily flip Simons to another team to bring back a cheaper player. He's 26 years old and trading for him brings his Bird Rights as well, so a team willing to pay him beyond this upcoming season can acquire him at a bargain price. Because the Celtics are clearly trying to cut salary, the acquiring team might find them a bit more amendable to some offers Portland wouldn't consider.
So my instant reaction to this move is to wait and see what Brad's next move is. I don't get the feeling everyone in the Boston front office is shaking hands and congratulating each other on a job well done just yet. There's more to come.
Which, if I may take my own list out of order, is why I don't think keeping him long-term is the play. I'm assuming he wants a raise, and I don't think Boston is in position to give him one. I'm not saying it's out of the question, it just doesn't make sense given what Boston's been planning.
Unless, of course, there's a big trade coming for Jaylen Brown and Simons at $30 million is a more palatable option for Boston moving forward.
I just don't buy that as Boston's thinking. Simons is a very talented offensive player but he's a defensive liability. The Celtics value positional versatility, and 6-foot-3 defensive turnstile Anfernee Simons doesn't fit that bill. I don't think he's the long-term answer for the Celtics.
But in the short-term, he'll be a nice fit. He kind of perfectly fits the "minimize the damage" part of the offseason for Stevens. The Celtics are going to be without Jayson Tatum for most, if not all, of the upcoming season and Simons can help make up for that loss of scoring. He's strictly an offensive player, but he's capable of putting up some gaudy numbers.
He's a high-level shooter who would thrive in Boston's offensive system. He had nine 30-plus point nights this past season and 13 games with five or more made 3-pointers. He's averaged 21 points per game over his past three seasons and he's a career 38% 3-point shooter. Starting Simons with Derrick White and Brown on the perimeter would lead to a lot of points being scored this season.
But the defensive issues would make having a rim protector behind him imperative. That would probably mean Kristaps Porzingis staying put in Boston, at least to head into the season. I can't imagine a team with Simons trying to defend up top without backup behind him.
If the Celtics were to keep him, they could try to go down one of the two previously mentioned paths. They could hope to increase his value under Joe Mazzulla's system, get him to show he's capable of being a second or third option on a decent team, and then use the pressure of the trade deadline to extract even more value for him.
Or, if they think Tatum could return in time to make a real playoff push, they could keep him for one more run and then let him walk and count his expiring contract as a big tax savings. Simons and Porzingis add up to more than $58 million in expiring contracts. They'd have to spend some money to fill out their roster after that, but that would add up to a monster financial savings.
My best guess is that Simons is moved either this summer or during the season. But whatever the decision is on him, Stevens comes out of this all as a big winner just because of the options he's given himself with this move.
He now has a 26-year-old with elite offensive skills on an expiring contract instead of a 35-year-old owed more than $100 million over the next few seasons. The Celtics have saved some money and can save more with some subsequent moves, whether they involve Simons or not. They have the option of moving him now, keeping him and moving him later, or letting him walk after one more stab at a championship. And hey, if for some reason it works better than expected, they could always pivot and keep him.
This is just the beginning for the Celtics this summer, but it's a very nice start for Stevens and his front office.