Tax Planning

Boston Celtics Mailbag: Derrick Rose, Night time Buying and selling and Luxurious Tax Planning

During the Celtics offseason we run a weekly mailbag. If you have any questions about the Celtics or the NBA, email brobb@masslive.com or tweet @briantrobb. Now let’s get to this week’s questions!

What do you think the starting XI will look like if they step down from Evan Fournier? & Which point guard on the market do you think they can afford / are most likely to come from? Patty Mills? Is smith? Reggie Jackson? Cam Payne? Many Thanks. I’m glad you answered my question last time. – Eddy B.

Hey eddy! When Fournier comes back I would think they’d be rolling with the Smart / Fournier / Brown / Tatum / Rob look to try and maximize their offensive versatility along with a range of switchable perimeter defenders. It is fair to ask if Udoka would prefer Fournier in the sixth man role to take on the banking offensive, but I think a chance to start as a third option will be a selling point for Fournier when the team brings him back . The bigger question will be whether Smart and Fournier will both be Celtics for the next season, as that would limit some of Boston’s long-term payroll options if Fournier signs a long-term deal.

As for the point guards, Mills feels like a pipe dream for Boston’s middle-tier tax exemption (he should be offered the full middle tier by someone), though it’s possible Udoka could approach him as the new head coach given his connection with San Antonio . I’d think Reggie Jackson, after his strong postseason run at the Clippers, is getting a payday somewhere greater than $ 6 million as well. Ish Smith and Cam Payne would both be available for taxpayer funding, although their size constraints would be an issue. Payne’s age, 26, suits him better than Smith if the two of you are offered a long-term deal.

What are the details of Brad Stevens’ contract? Does the extension he signed match POBO’s position when he was the coach when he signed? – YES Espinoal

Nothing is publicly known about her, likely because Brad’s agent is his wife, Tracy (who is also a lawyer). We do know, however, that he received a five-year extension last August, which likely began after this season. I doubt there was a big salary adjustment with the move to the front office, but I’d bet Stevens still has the long-term security from the original addition.

I’ve been thinking about this for a long time and find it very useful. Charlotte has never got behind the wheel and has 3 starting caliber strikers; Hayward, PJ Washington, and Miles Bridges. Bridges comes in for extra time and he comes off the bench except when Hayward is injured. He plays with a lot of fire and became the first 50/40/80 player in the history of the Hornets last year. It’s on the rise and I think it could be got. Charlotte likes cost-controlled assets. The deal – Boston gets Miles Bridges, Charlotte gets Langford, G. Williams and a 1st. I would like to do without more. —Ed

It’s a fascinating idea, but I doubt the Hornets focus on it. Bridges is an aspiring young player who has done far more in his career than G. Williams and Langford. Given the Hornets have a lot of room for caps, I doubt they’d want to relocate an aspiring young man for a couple of Boston’s unproven.

Why don’t I see any news about Rose possibly coming to Boston? I honestly think he would be great with the Jays and possibly not even that expensive. Rose is not the dominant goalscorer he once was, he is more patient and would be an excellent passerby to compliment them. – Maurice

Rose had a lovely resurgence in New York at the age of 32. His strong bond with head coach Tom Thibodeau likely makes him a strong prospect for a new contract as the Knicks have a lot of money to spend and Rose shouldn’t break the bank. However, with the Knicks targeting bigger names in the freelance agent market, Rose could be available for mid-range dollars. The problem for the Celtics? He likely played himself into a contract bigger than the median taxpayer ($ 6 million) after a stellar regular season campaign. Health issues will limit the length of his next deal, but the Celtics don’t have the resources to outbid others for him in the open market.

Hello B-Robb,

Thank you for your CS reporting. Love to hear and read your insights. My question has to do with Brad’s speech on financial flexibility. What can the Cs realistically do this off-season to improve the team, but still be able to sign a big free agent like Beal in the next off-season? Renewing Smart or Rob Williams and re-signing Fornier are options now, but would either move essentially take a beal off the table unless we deal with Jaylen? I would love to see a Tatum-Brown-Beal combo here. – Gregor

The path of planning for Bradley Beal or any other star is difficult. The Celtics haven’t tied up a lot of cash after this season other than the partially guaranteed contract from Jayson Tatum, Jaylen Brown and Al Horford. That could change quickly, however, as key contracts are being awarded to Fournier, Smart or Rob Williams this off-season.

The question the Celtics have to answer is whether maintaining cap space for a maximum free agent in the near future is a priority for the future. If so, getting any of these guys on long term contracts would be an obstacle when it comes to keeping the cap room open for a guy like Beal. What is more important, however, is the risk-reward balance in this scenario. Does it make sense to lose a guy like Fournier only to sign a star like Beal with no guarantees that he’ll be available in a year? This part of the equation will make it difficult for Boston’s front office to weigh up.

The other possibility here is that the Celtics are content with simply storing assets to target a star (while attaching round one selection) and maintaining the team’s own talent in the near future would be essential to that quest. The Bucks took this route last off-season when they traded in most of their draft assets and some talent for Jrue Holiday. Right now, this is probably the most likely route Boston will take, but it’s not necessarily the one that gives them the most flexibility.

Try to get back to the first round if someone you love slips. I think Knicks is 19 and 21. New York already has enough young players who might want to postpone one of those picks. – Jablonski

I agree with you that the Knicks may be trying to trade, but I would suspect they are trying to box these picks to level up rather than trade. The Celtics likely agreed to postpone their pick for the first round this year as they didn’t want to add another young man to a crowded squad that could drive up their tax bill. Because of this, I doubt they’ll go back to this first round unless they clear some veteran salary (Marcus Smart, Tristan Thompson) with the deal.

What are the effects of last year’s tax avoidance moves (Theis, Kemba) on the prospects of keeping Tatum / Brown? – Tyler

It has no real impact on this duo in the short term. What the tax avoidance did last year is to reset the clock to the later line for some repeated tax penalties. That could help the Celtics owners avoid a paycheck with max deals for Tatum / Brown and a third star in 2023. For now, tax avoidance only saved owners some money last year by relocating a player who was likely out of the question to be re-signed in Theis this off-season.

Send any questions for a future mailbag to brobb@masslive.com

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