Philly Front Office

Just because I don’t like Jayson Tatum or the Celtics, don’t take this article as if I’m happy he got hurt. That being said, from a jealous Sixers perspective and from a person who gets off at salary cap rules, I am giddy to go into the financial ramifications of the Celtics problems. In one night, they morphed from an expensive contender to a second-tier financial blackhole…just in time for new ownership to take over. They have options, but they can’t like the questions they will be forced to answer.

Going into the playoffs, I was already saying they likely had to make some moves next year just because their team was so damn expensive. The NBA has tried to deter billionaires from dumping unending dollars onto superteams by instituting a punitive tax that gets increasingly more expensive the wider the wallet gets opened. If the Celtics bring back this team by not moving any contracts and resigning Al Horford, they are looking at a $250m payroll AND a $300m tax. That’s bonkers. While it is certainly doable for the new owners, billionaires don’t like paying taxes period and weren’t likely to run back the team completely. Even shedding $10m would save around $80m in taxes.

It’s one thing to contend for $500m+, but it is completely different to spend like I did on paycheck day in college when the team isn’t a contender. Oh yeah, if Jayson Tatum can’t play next year, the Celtics are not a contender. They are still pretty good (and will undoubtedly still beat the Sixers), but they are not a contender as assembled with $54m of Tatum on the sideline (I know this because the Sixers have a similar problem). So what are they going to do?

Who Do They Trade?

Keep in mind with any possible trade that the Celtics are over the 2nd Apron. This means they cannot aggregate salary (can only trade one guy at a time) and can only lower their salary by a certain amount depending on who they trade with. They also surprisingly have draft picks to spend including this year’s #28 pick and next year’s first.

Let’s take a look down the line of Celtics players. Even though Sam Hauser and Payton Pritchard make only $10m and $7m each, these are very good deals for the Celtics and not likely to be on the block. They are surplus value contracts and the types that either help the team on the court or who could be used in trades down the line. Those two are likely staying.

Kristaps Porzingis is in the final year of his contract that pays $30m. They can’t just kick him into the sun to get rid of him. Even moving him to a below the cap team like Brooklyn or Detroit would be difficult because some salary needs to come back and they do not really have the right contracts to match with. It would also likely cost Boston a first round pick, not unlike the Sixers moving Al Horford 5 years ago. Instead, considering how much he is currently underwhelming, if they move him at all it would likely be for someone who makes slightly less money and isn’t as good. I could see some kind of 3 way deal that sends Andrew Wiggins to Boston to basically quadruple down on their strengths in the absence of Tatum. This only helps their financial problems a little bit though. That being said, when you are dealing with an 8.5x tax multiplier, every dollar counts.

What about Jrue Holiday? Considering he has more real value than Porzingis, the Celtics could opt to move Jrue and either still trade Kristaps or just let his contract expire by the time Tatum returns. A lot was made of Holiday not exercising a player option for more money in order to sign an extension for slightly less annual value. That helped this year’s possible tax issues considerably. Yes, it helped, but now he is starting to decline with 3/$105 left on his contract. Is Jrue going to be any good in 2 years when Tatum comes back? I wouldn’t bet on it (what a career he has had by the way). Boston could get a first round pick back for him this year while also lowering their tax bill. Could they trade him to Detroit for Tobias Harris and a draft pick? This might help with tax relief, but it makes them worse on the court.

Derrick White has exploded as a Celtic and might be the single most valuable piece they have on the team right now considering his contract. He just does everything right all the time. It’s unbelievable. I doubt he is getting moved, though there would be suiters.

Would the Celtics consider trading Jaylen Brown? His max contract pays about $235m over the next 4 years. He’s undeniably good, but also can’t dribble. The Spurs are going to be on everyone’s mind this summer after getting the #2 pick in the draft. Would Boston consider moving him for #2? The Spurs are likely going to go for Giannis, but if they can’t land him, could they pivot? Brown is a star and there is always a market for stars. It’s just a question of whether Boston wants to get cheaper or younger. Dylan Harper, Devin Vassell, Keldon Johnson, and another pick for Jaylen Brown. Who is saying no? This could make Boston younger, cheaper, and possibly better in the long term, but does not help them contend next year or even the year after.

The big move is something Celtics fans do not want to think about. Could they trade Tatum??? Let’s say Boston still wants to go for it. Would they consider calling Memphis, New Orleans, Atlanta, or Phoenix? Basically, anyone I mentioned in my Star Trade article is up for grabs in a Tatum trade because they are damaged and unfortunately so is Tatum. Ja Morant, Zion Williamson, Trae Young, and possibly even Kevin Durant are all possible movers this summer, but their values are very murky for various on and off court reasons. No picks, nothing else, just 1 for 1 trades of damaged stars for an injured Tatum. Tatum is better than all of these guys, but he also might not ever be the same. Is this a risk those teams are willing to take? How bad does Boston want to contend going forward? It should be noted that everyone on this list but Durant makes less than Tatum. This is the option that Milwaukee doesn’t have to keep Giannis happy. There is no market for an injured Damian Lillard, but Jayson Tatum is completely different despite it being the same injury. Theoretically, anyone who gets him is buying low on a star who Boston would never normally consider trading. Is new ownership really ok with throwing away a year of being a contender? This might be the only way to get cheaper and still be a threat.

(A straight Durant trade does not work by around $500k because they are both second apron teams. Boston would have to get under the 2nd apron first. I’m leaving it in here because it is just too juicy and I am banking on someone being smarter than me to try to pull it off)

PS…Trading Tatum is the only way I see Boston bringing back Al Horford now. With such a punitive tax, why would you spend $10m on a complimentary piece who has nothing to compliment? Good riddance Boston Al Horford.

So What Happens?

Boston is in the strangest of binds. They are a contender that can’t contend. They are expensive but for no reason. They could move contracts to get cheaper, but where does that leave them going forward? They don’t want to just waste contracts and picks and not improve the team. Most of the ideas above are about getting cheaper and younger rather than actually better. That’s because they are currently maxed out. This is exactly the crossroads that the NBA was hoping to design with the advent of the new CBA rules. The smart but dull money is on Boston moving Holiday or Porzingis and waiting out a year. New ownership could really makes things interesting though. We don’t know if they will want to stay the course or make their mark. Moving Tatum would DEFINITELY be leaving a mark. This would shake the league as a whole in a way it is not prepared for. Do not count this out.

The Celtics now have to choose between saving money, wasting a year, and contending right now. So, are the Celtics f****d? It’s up to them. It’s not an easy choice.