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Isaiah Thomas must wait for his Brinks truck while Danny Ainge makes moves

At his exit meeting Friday, Isaiah Thomas told reporters that he would be willing to wait for a potential contract extension so Danny Ainge can deliver another star or two. But the unilateral patience required from IT could leave him without a chair when the music stops.

Cleveland Cavaliers v Boston Celtics - Game Five Photo by Adam Glanzman/Getty Images

For a hyper-aggressive player, Isaiah Thomas is impressively committed to being patient this offseason. As he awaits a decision on whether to have surgery to repair his torn labrum, Thomas is now facing an uncertain future.

Entering the final year of one of the most absurdly valuable contracts in the NBA, Thomas and the Celtics are approaching a crossroads, where they will attempt to build a title contender for now and the future. But if they can’t fulfill their plan to acquire a pair of All-Stars by free agency and trade, they will face some difficult decisions on whether to adjust their current path.

That is where Isaiah Thomas’s next contract hangs in the balance. The Celtics don’t set goals short of championships. They don’t build up teams to win one title. They build dynasties. They look at the most recent Big Three as a bittersweet period in time, where they reached their incredible achievement in 2008 and then fell perilously close for the next several years.

Danny Ainge and his front office have an opportunity to very carefully put together a team that is both elite in the short term with the potential to grow into a second elite phase in the future. That’s something Isaiah Thomas says he wants to be a part of and is willing to be patient for his own reward to let Ainge work his magic.

"(An extension) means more money? Yeah, I would love that," Thomas said. "But if it don't happen, I'm the last person to be bothered by that. I know everything happens for a reason, so when my time comes, I know it will come and God will bless me."

One day soon, a figurative Brinks truck will back up to his locker as the doors swing open and piles of cash come flooding out. But after spending his career searching for a home like Boston, he will wait until the opportunity comes his way.

"That time will come," Thomas said Friday at the Celtics’ exit meetings. "Whatever happens, happens. I've proved myself. The world knows what I bring to the table and I can't do anything to control anything else. So whatever happens this summer with contracts, it happens. If not then we'll wait until next summer and then we'll see where we go."

Thomas hits free agency next summer, where he is due for a massive payday. He wants up to a five-year max deal to stay in Boston, but his injury situation and age—he turns 29 in February—means concerns of his durability and performance over the life of the contract could dissuade potential four-year max offers on the open market. But Thomas clearly performed at a max level this season and should eventually bounce back from his hip injury to be a great player once again.

His value to the team went beyond being an elite scorer this season, as Thomas proved himself to be a great leader on the floor and in the locker room. He is the ideal Celtics star, but the Celtics drafting Markelle Fultz could lead to scenarios where the Celtics may have to commit money elsewhere.

Owner Wyc Grousbeck could dig into the eventual repeater tax with a wide smile to give Thomas that Brinks truck in addition to signing a max free agent this offseason, but that repeater tax could become astronomical if they re-sign Avery Bradley at a market rate in the low $20 million range and extend Marcus Smart, as Ryan Bernadoni of CelticsHub detailed.

This means everyone is going to need to take a steep hometown discount. They had to max out Al Horford to bring him in, and they will probably need to do the same with Gordon Hayward, something they can pull off by removing non-guaranteed money from the books and potentially stashing Guerschon Yabusele one more year. Sources have indicated that Yabusele may be stashed one more year for fiscal prudence, especially as he recovers from surgery to remove bone spurs from his feet this offseason, which should have him returning to the court by the time training camp comes around in September.

"We need the best possible player that's gonna help us win, and I'm with that,” Thomas said. “Anything Danny (Ainge) and this organization need me to do to help bring even more talent to this city, I'm all for that. I want to win a championship, and being so close to getting to the finals, that makes you want it that much more. I'm all help if they need it. I'll be around.”

Thomas is aware of the payroll constraints imposed by signing a max free agent, but he has been pretty adamant that his priority is rings and he wants as much talent as possible surrounding him to do it. He could sign an extension later in the offseason if they slip under the cap, something that may require unloading Demetrius Jackson and Terry Rozier to pull off if the cap remains at $101 million. But he wants to give his team a chance to load up around him before that happens so they don’t get their butts kicked again next year.

"We definitely need more. It was obvious. But shoot, the number one seed and getting to the Eastern Conference Finals, like, we had a pretty good year. But to take that next step, which is the Finals, and to do whatever we can to beat Cleveland, we definitely need more. So I don't know what those guys are going to do with this team but I would love to see everybody back and add a piece or more."

The irony is that while they did have a good year and they are proud of getting as far as they did, they still failed their season objective. There is much to take for getting as far as they did and playing two competitive games in Cleveland. It is a sign of progress overall, but a failure nonetheless.

“I don't have any objectives other than winning the whole thing,” coach Brad Stevens told CelticsBlog in his press conference after their season ended Thursday. “To me, that's the only goal you shoot for because then if you don't, if you put your goals lower, then you create a ceiling for your team, and I don't think that's fair to your team.”

That leaves Ainge with his biggest challenge yet. Many GMs have built good, competitive teams over the past few years. There were three great teams in the conference finals, with the Warriors clearly on their own plane and the Spurs limping to a merciful early demise. Boston looked like they had wandered into the wrong bar and tried to play cool.

“I feel like wins are deceiving sometimes,” Ainge told the Boston Herald. “I think that the fact that we were one of three teams still left playing was something to be proud of, but it’s not necessarily where we really are.”

The drastic results were a pretty clear indicator of this sentiment. The silver lining of the Ewing Theory kicking in for Game 3 showed the potential of the Stevens system to be something unstoppable reminiscent of the 2014 Spurs. But it was just a lining to an overall underwhelming core in the end.

“If we’d lost Game 7 against the Wizards, I don’t feel any different than if we’re where we are today. I know that we’re good. I know that we’re not great. I know that we still have more to do, and, you know, that next step is by far the hardest.”

The Warriors’ path to their current team illustrates the challenges that makes this step the hardest. Not only are the Warriors quite possibly the most talented roster assembled since free agency overhauled roster building, but they have done it with older and therefore cheaper contracts for the stars they drafted. They were coming off their rookie deals and were entitled to smaller maxes, plus Curry was signed right before he put his ankle injury woes behind him and evolved into an all-time great. The Celtics have to pay their top talent at current market rates deeper into their careers. Squeezing everyone in is a major hurdle.

If this Boston team settles for a compromise between building a great team and making incremental improvements, it may find itself stuck in the mediocrity of being good. It’s the kind of jam Masai Ujiri may find himself slipping his Toronto Raptors out of this year. Boston is aware that signing just Gordon Hayward and drafting Markelle Fultz will probably not make this current core a title team in the next three years.

“Just because you’re one piece away doesn’t mean you can get it. And if you force yourself to get it, and if you force a deal or force yourself to get the second best available or the third or fourth best available player at that position that you need, then it might not make you that much better or make you still not good enough, and you’re stuck. So, yeah, we’re not that far away, but we’re still a ways away. We still know we need to get better. Everybody in our organization knows we need to get better. We need to add.”

Ainge’s words move the market like the Federal Reserve chairperson, hinting at when and where the next big splash may come. The league is well aware that Ainge will at some point do something that will shift the balance of power toward the Northeast corner of the country in the future. How near that future may be starts with a potential draft night trade and becomes much more clear when Gordon Hayward’s next contract is agreed upon this July.

Boston is in a unique position to draft Fultz, trade next year’s Brooklyn pick and some of their starters for an All-Star, and sign another All-Star in Hayward. That would be a sonic boom that would lift them into contention while still having some potential All-Stars developing in the background. They might not be as good as Golden State with that roster, but they would be very competitive while having a clear path to a great team around Fultz five years down the line.

Or it could all be blown up as they look to stock up on blue-chip prospects.

“There is a potential for there to be some significant change,” said Ainge. “But maybe less change. Maybe more change; maybe not. A lot will be dependent on what we’re able to pull off in the draft and in deals leading up to free agency and then what happens in free agency. There’s just so much unknown right now. Right now it’s all talk and pipe dreams and planning. But there’s no certainty. It’s an exciting time for us, and it’s a very busy time for us.”

While they have infinite plans and models in place to adapt to situations on the fly in real time to make any little move that pops on their radar, there is a clear mission statement.

“We have a lot of good players,” he said, “but we need some great ones.”

There are some clearly identified players that would fit into the great category. There are plenty more that aren’t even on the radar. Ainge has a track record of going off the grid to find his prize. He’s been overwhelmingly successful and now lucky with his moves so far. But this was all a dress rehearsal for his biggest performance, and the lights in the lobby are flickering. Isaiah Thomas is making his way to his front-row seat.