The Celtics jumped out as one of the most logical suitors for Holiday as soon as he became available. They have an appetite to increase spending and more than enough matching salaries. More importantly, they had more than enough draft equity to meet Portland’s asking price with up to five first-round draft picks available to trade.
Reports immediately came out that the Celtics were in the bidding for Holiday, and speculation began on what the package would look like player-wise. They needed to send out $33.3 million to match, and Malcolm Brogdon ($22.5 million) was penciled in as the likeliest to go. How they were going to come up with the remaining $10.8 million was a mystery.
Celtics fans hoped that neither Robert Williams III ($11.6 million) nor Al Horford ($10 million) had to go. Many prayed that a framework presented by The Athletic’s John Hollinger featuring Payton Pritchard ($4 million), Luke Kornet ($2.4 million), Sam Hauser ($1.9 million), Jordan Walsh ($1.1 million), and Blake Griffin ($3.2 million) via sign-and-trade would’ve sufficed. The Celtics chose to push their chips by including Williams III and worry about fixing their frontcourt later.
Make no mistake, Holiday increases Boston’s title odds and makes the Marcus Smart for Kristaps Porzingis swap make more sense. They now have two of the best defensive guards in the league, in Holiday and White, to throw at Lillard in a potential matchup against the Bucks. The Lillard trade now has a touch of disaster potential for the Bucks, considering it indirectly significantly improved a top rival.
Holiday likely had a big say in his destination, considering his contract situation. He is entering his age 33 season and could become a free agent next summer. Any team acquiring him needed to factor in what he’s seeking on his next deal, what the market could look like for him, and how he’ll age over the next few years.
The Celtics wouldn’t have parted with two first-round picks and two valuable rotation players if they weren’t ready to commit to him. Holiday will be extension-eligible starting on February 22 but can only add two years, provided he declines his $39.4 million player option. He could add up to four years, starting six months from now, and can extend at a lower starting amount than his player option amount, thanks to modifications to the extension rules in the new CBA.
Holiday could also pick up his $39.4 million player option and then extend on a team-friendly amount. This would be similar to what the Celtics did when they acquired Kristaps Porzingis and extended him for two years, $60 million, after he picked up his $36 million player option for 2023-24. With so many options toward keeping Holiday long-term, expect both sides to get a deal done at some point.
Adding Holiday is yet another big commitment to a nucleus that is already projected to be deep into the tax over the rest of the Jayson Tatum and Jaylen Brown era. This deal will increase their tax penalty this season by $14.4 million once they finalize their 14th player, totaling a $222.6 million roster. They are likely looking at a $260 million roster next season once Brown’s supermax extension kicks in.
The real pain will start as soon as the 2025-26 season when Tatum’s supermax kicks, which he will be eligible to sign starting on July 6, 2024. They will be paying both Tatum and Brown over $50 million each while entering the repeater tax in the year when higher tax rates in higher tax brackets get implemented. They could be looking at a roster in the $350-400 million range, assuming they extend both Holiday and White to lucrative deals.
In the meantime, Boston will now look to tackle their shakier frontcourt. They’re already making moves on the margins by agreeing to bring Wenyen Gabriel to camp and could pursue other options like Nerlens Noel, Bismack Biyombo, and Blake Griffin. They could also trade for any big man on a minimum salary without sending anyone back.
They could also look at the trade market for a big, but that could take some time. First and second apron trade rules for this season limit the amount of salary they could get back in a trade. Their biggest means is a $6.2 million trade exception, but that might not be enough to acquire a player who could reliably play in the playoffs.
A path they could take toward trading for such a player is using that trade exception soon on a player that fits within it. Then, they could aggregate that player two months later with other salaries to acquire a more expensive player. For example, a $6 million player combined with Pritchard and Kornet could bring back a player earning just shy of $14 million. Such a scenario significantly opens up their frontcourt options on the trade market. The Celtics can still trade up to two first-round and eight second-round picks this season.