Celtics Mailbag: Joe Mazzulla game management, looming tax issues

The Celtics have hit a rough patch for the first time in months, dropping two straight games this week including a loss to Nikola Jokic and the defending champions Nuggets. With Boston now having gone 1-6 against elite teams since January, it’s time to tackle a few questions about where this group stands among contenders. If you have questions about the Celtics or NBA, email brobb@masslive.com or tweet @briantrobb

Suppose Boston doesn’t secure the championship; how might the roster shape up for the next season? It seems challenging to extend contracts for players like Jrue, White, and Tatum with a super max. What kind of offers do you anticipate for D-White and Jrue? Lastly, which free agent do you think would be a good fit for our final roster spot (among the FA)? — Thanks El Pogi

This is a very loaded question but is certainly something that deserves attention given how many chips the Celtics pushed to the middle in this campaign. It all depends to a large degree just how much ownership is willing to spend on this group. There’s nothing from keeping the Celtics from simply running it back if Jrue Holiday opts in and/or signs a longer extension. However, the shelf life for potentially running it back ends in the summer of 2025 when the super max contracts kick in fully for Boston’s stars and higher luxury tax penalties for repeaters also take form from the past CBA.

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The guess here is the Celtics simply kick the can on tough choices until that point barring a disappointing finish in the postseason (Eastern Conference Finals or earlier?). If Boston can bring back Holiday on a reasonable deal, they likely will feel they have a lot of appealing contracts that they should have no trouble moving off of for assets for whenever that time comes.

Any offers for White or Holiday would be significant. White probably has more value now due to his age after his breakout play this year but I think you are looking at 2-3 first round picks and/or promising young talent for either guy. Ultimately, moving one of them later this decade probably makes the most sense from a depth standpoint on paper but dealing a bigger contract (Brown?) may ease the financial and team-building burden even more. If the Celtics have won a title by 2025, the odds of that go down significantly. If not, something will have to give by that point in all likelihood.

For free agents, there’s not a lot that has a ton of appeal out there at this point. If the Celtics remain healthy heading into the postseason, trying to bring aboard a little more emergency depth in the backcourt could have had appeal. Would have liked Delon Wright

How can they get Tatum going when Denver is being very physical & throwing him off? Should they go double big vs the Nuggets every time? KP and 1 of Al or Tillman but not those 2 together? —Truthfastino

Tatum just didn’t seem to have it on Thursday night against the Nuggets, particularly with his reads. He was going through the motions with some of his passes off double teams and that led to turnovers and easy transition buckets. Denver is a smart defensive team and they made the Celtics look predictable for a good chunk of that win. Tatum needs to recognize that to keep the pressure on.

As for double bigs, I only like that lineup against the Nuggets when Jokic is on the floor. For some reason, Joe Mazzulla went to it a bunch against a Jokic-less bench unit for Denver and it seemed to hurt Boston on both ends. The Nuggets were smaller and faster than Boston, leading to tough rotations for the bigs, meanwhile the Celtics’ offense seemed to be bogged down with Horford/Tillman not able to punish mismatches. Would like to see Mazzulla better configure the rotations next time around.

Why can’t Mazzulla do better than a contested JT fadeaway with the game on the line? — Steve

For all the improvements that Mazzulla has made this season, the crunch time issues have lingered. Joe Mazzulla still isn’t calling a timeout in these spots but the players on the floor haven’t shown any real growth with their decision-making. Jaylen Brown and Jayson Tatum have had plenty of uninspiring sequences that led to long contested jumpers and clock management has been a problem for both guys as well. There’s been enough of a track record now where it’s time for a change. Mazzulla needs to either start calling plays the team can get into quickly, call timeout or simply put the ball into the capable hands of one of his guards (Derrick White or Jrue Holiday). Those two can at least be counted on to move the ball and that should be a good thing for a stacked Celtics closing lineup in a tight game facing a deficit.

Should the Celtics let Jrue Holiday shoot more on a night when others don’t have it? — Ty

His shooting percentage certainly says yes. He’s up to 44.3 percent from 3-point range on the year yet his usage is the lowest it’s been in his entire career. Part of that is Holiday’s willingness to sacrifice for four superb starters in the lineup around him. However, as he’s grown more comfortable within Boston’s offense, it feels like he’s been forgotten about some nights. Opposing defenses try to take advantage of this at points by leaving inferior defenders on him (Nikola Jokic) and Holiday still has enough in the tank at age 33 to punish defenses for this. Finding the right balance for Holiday going forward will be crucial for this group.