Hollinger:
Let’s start with Boston, though, because this was another tremendous swap by a front office that has won nearly every trade for the last half decade.
The most amazing thing about this trade is that the Celtics got off the final two years of Holiday’s deal while receiving draft picks instead of sending them out. The three years and $104.4 million left on Holiday’s deal projected to be deeply underwater value-wise; I wondered whether the Celtics would have to give up two firsts to move off his money or whether they could get away with one.
While Holiday is still a plus defender and an A-plus in the locker room, my BORD$ formula valued him at $19 million for the coming season – nearly identical to how it rated Simons – and he’s making nearly double that. Presumably, his age-36 and age-37 seasons in the two years after would project worse, but Holiday's salary rises in those years.
Setting aside what Simons can do on the court, the sheer value of dropping the final two years of that contract for Boston is massive. Simons, however, is a real basketball player who is on an expiring contract that pays him $27.7 million this coming season.
Boston could theoretically extend Simons’ deal, but that would only make sense if the Celtics were moving another big contract this summer. Otherwise, the next move for the Celtics might be to keep whittling down their cap number in a series of subsequent trades. Imagine, for instance, Boston flipping Simons to Sacramento for Malik Monk and Devin Carter, then flipping Monk to Dallas for P.J. Washington, then flipping Washington into a team’s nontaxpayer midlevel exception for a draft pick.
I’m not saying any of those trades are likely or even being discussed, but I am giving you an example of how the Celtics can stairstep down from Simons’ $27.7 million, to a combined $23.7 million for Monk and Carter, to $14.1 million for Washington and $4.9 million for Carter, to just holding Carter’s rookie contract for $4.9 million and being under the second apron. There are infinite pathways to doing something like this; also, it’s possible the last step can be done in-season.
One way or another, however, the Celtics are nowhere close to done, because the incentives for them to reduce their luxury-tax penalty (including a punitive repeater tax) and unfreeze their 2032 draft pick (by staying below the second apron three times in the next four years) are overwhelming in a “gap year” where Jayson Tatum will miss the season recovering from a torn Achilles.
