The lottery-winning Celtics now face an Isaiah Thomas-related dilemma

In a span of 24 hours, the Boston Celtics won a Game 7 and the No. 1 pick in the 2017 NBA draft. In another 24 hours, they could add a Game 1 Eastern Conference finals victory to their tally. So yeah, things are going pretty well in Boston. And with so many promising young players and future assets — thanks, Brooklyn! — they should continue to go well for years to come.

But the pingpong balls also put the Celtics in a sticky situation, one that revolves around the most underpaid player in the league. Isaiah Thomas is on a contract that pays him an average annual salary of $6.75 million. But not for long.

Thomas is the heart and soul of the Celtics. His rise from the last pick in the 2011 NBA draft to All-Star has been extraordinary. His 53-point performance against the Washington Wizards in Game 2 of the Eastern Conference semis was legendary. His fourth-quarter exploits all season have been heroic.

All of this will likely make Thomas a max-contract player sometime in the next 14 months. Boston now has to decide whether it will be the team to give him that max contract, and its decision goes hand in hand with its use of the No. 1 pick in the draft.

Many expect that pick to be Washington guard Markelle Fultz, the consensus top player in the class. The Celtics could consider trading down to take a wing like Kansas’ Josh Jackson or Duke’s Jayson Tatum, but you don’t pass up a player like Fultz unless the fit is disastrous. And the Thomas-Fultz fit is far from disastrous, despite positional similarities.

The fit is the least of Boston’s concerns. Danny Ainge, the team’s president of basketball operations, says he thinks Thomas can play with anybody. Fultz says the two would be a “great backcourt.” They’re probably right. Celtics coach Brad Stevens already likes to take Thomas off the ball. Fultz is a multi-dimensional scorer who can play off the ball, too. Both are accurate shooters off the catch. Plus, regardless of skill sets, when you put two talented guards on the floor together, more often than not, the results are positive.

Sure, there could be issues on the defensive end, where the 5-foot-9 Thomas is a liability, and Fultz wasn’t exactly known as a lockdown defender during his lone year on campus. There’s also the conundrum of how incumbent Celtics guards Avery Bradley, Marcus Smart and Terry Rozier could fit into the same rotation as Fultz and Thomas. But those issues are secondary. For the most part, Fultz would work in Boston.

Isaiah Thomas is an All-Star, and he’s the Celtics’ catalyst, but will Boston give him a max deal? Should they?
Isaiah Thomas is an All-Star, and he’s the Celtics’ catalyst, but will Boston give him a max deal? Should they?

Could a Fultz-Thomas backcourt lead the Celtics, as currently constructed, to an NBA title? Maybe, but probably not. That’s why Boston is in the market for another star in the mold of Paul George, Jimmy Butler or Gordon Hayward.

The Utah Jazz All-Star can choose not to exercise the $16.7 million player option he holds for next season and become an unrestricted free agent this summer; if he does, the Celtics are expected to make a run at him. George will hit the free-agent market in 2018. Both George and Butler have been subjects of trade talks.

The issue for Boston is that it also must pay Thomas — if it wants to lock him up long-term. It has two options in that department

Draft Fultz, re-sign Thomas

One is to renegotiate an extension with Thomas on the three-year anniversary of his current deal, July 12. That new contract would run through 2021-22, and its total value would be in the range of $145 million. The roadblock here is that such a deal would require cap room, which the Celtics might not have if they sign Hayward. Free agency begins on July 1, and teams can officially sign players beginning July 6, so a deal with Hayward would likely have to be done before a restructuring of Thomas’ contract. In the other direction, a renegotiated deal for Thomas would impede Boston’s pursuit of Hayward this summer, or of George next summer.

So why not wait until next summer and re-sign Thomas when his current contract expires? That’s the second option, and its the one that would allow Boston to maximize the talent on its roster in 2018 and 2019, and perhaps beyond. That’s because it could use Thomas’ Bird rights to go over the salary cap to keep him around.

But this option poses its own problems. The Celtics would be giving a 5-foot-9 guard roughly $36 million per year through the 2022-23 season, during which Thomas will turn 34. They would be tossing away any cap flexibility they still had for years to come, and limiting their options going forward. With Fultz on board, a plethora of young talent improving and more high draft picks to come, would that be a smart move? More on that in a bit.

In the meantime, in 2017-18, Thomas, who has been overlooked his entire career, would be neither Boston’s point guard of the future nor one of its five highest-paid players. The Celtics would be specifically delaying his payday to hand a massive check to another big-name free agent.

Thomas, after seeing the size of other contracts last summer, joked that the Celtics “better bring out the Brinks truck” when his contract negotiations rolled around. “They’re paying everybody else, I’ve got to get something,” he said. If Boston came to him with anything less than the max, would he consider leaving?

Boston’s front office must factor in all these scenarios and questions as it approaches the draft and free agency over the next two months. First, though, maybe the C’s must consider their timetable.

In a way, drafting Fultz and intending to max out Thomas is contradictory. Doing so neither commits to a win-now mentality nor maintains a long view. Sticking with Thomas could hinder future growth. Drafting and keeping Fultz would mean hanging on to an asset that will be far more valuable on the court three, five or eight years from now.

There’s nothing inherently wrong with planning for both the present and future. But straddling the line in a competition where the ultimate goal requires absolute superiority could see the Celtics come up short both now and further down the road.

So perhaps they should throw all their eggs in one basket. And if they choose the win-now basket, perhaps they should trade Fultz.

Trade Fultz for an All-Star

If the Celtics are serious about going for this, why not trade Fultz for a star in his prime? Boston could select Fultz No. 1 overall, sign Hayward on the first day of free agency using cap space, and then, a month after the draft, flip Fultz for an All-Star. That would give the Celtics a (small-ball) starting lineup of Thomas, Bradley, Hayward, the newly-acquired star and center Al Horford, plus a pretty solid and versatile bench (though a veteran or two would have to be included in any Fultz trade to make salaries match). That team could compete immediately with LeBron James and the Cleveland Cavaliers, and maybe even with the star-studded Golden State Warriors.

But would such a trade sacrifice too much of the future? The two names that have come up in trade rumors in the past are George and Butler. The issue with George is that he seems fixated on signing with the Lakers in 2018, so a trade with Indiana could end up being a one-year rental. Butler has been nagged by injuries in each of the past four seasons, and might not be the top-10 player the Celtics need to put them over the top. Other stars — cough, Carmelo Anthony, cough — could become available, too, but there is no one surefire target.

Selling out to try to win a title with the current core is the riskiest play of all. Given the current dual reign of the Warriors and Cavs, it might not be sensible. So maybe the best move is to maintain a patient approach, and…

Let Thomas walk … or trade him

This suggestion is tantamount to heresy in Boston at the moment, but if the Celtics want to win multiple Larry O’Brien trophies over the next 15 years — and that should be their goal — they have to at least entertain the possibility of chasing them without Thomas. And if they want to maximize Thomas’ value, do they do the unthinkable and trade him this year? If they want to delay true contention for another few years, do they deal a player like Bradley or Kelly Olynyk, too?

To trade Thomas would be to effectively sacrifice 2017-18 for an increase in title odds down the road. It almost certainly won’t happen. But the discussions surrounding a potential max contract for Thomas will be very interesting. The thought of handing out such a lucrative deal has to make Celtics fans feel queasy. But the thought of him leaving might spark outrage.

This is all hypothetical, of course, and the decision-making process will surely take various twists and turns over the next two or 14 months. There will likely be plenty of other options considered, too. There are other choices — such as the one surrounding Bradley’s contract, which is very similar to Thomas’ — that must be made, as well.

But the bottom line is this: With so many valuable commodities, including another unprotected Brooklyn Nets first-round pick coming in 2018, but with no true transcendent superstar currently on the roster, Boston will have no shortage of difficult decisions to make on its quest for a title. It’s an enviable position to be in. But that doesn’t make the decision any easier.

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