
The next two off-seasons will be pivotal for the Boston Celtics as they continue their climb back to legitimate title contenders. What makes this process easier is that they have a lot going for them. They’re virtually a lock to finish top-two in the eastern conference with their first 50-win season since 2010-’11, they are the owners of the Brooklyn Nets pick which has the highest odds of being No. 1, and they continue to overachieve with a congregation of castaways.
It’s the Celtics way. Or, it’s the Danny Ainge way. From bringing in Kevin Garnett and Ray Allen in 2007, to completing an NBA heist in 2012 by dismantling the Nets, the Celtics have had some serious success in planning for the future. Both moves, respectively, involved a lot of confidence from everyone in the organization and some pure Celtic luck. Now, Ainge has another conundrum on his hands. He can either trade the guaranteed top-four pick in a package deal for an impending free-agent superstar such as Paul George, or keep the pick and draft a highly touted prospect.
If Ainge and his staff go the latter route, their only option is drafting a guard. They can’t select another three-man with Jaylen Brown having NBA potential, Al Horford is locked up for the next three years after this season, and there are no known top-given centers in the draft. With that said, speculation can commence with either Lonzo Ball, Markelle Fultz, Malik Monk, or DeAron Fox possibly ending up in green and white… a great color combo like the mint cilantro sauce at Chicken and Rice Guys (reference only Bostonians will know).
So, let’s say Ainge doesn’t pull of the unthinkable and shakes up the NBA for a third time—even though it’s the charm—and is stuck with the draft pick. A guard with great potential is heading to the Boston Celtics. With a new back-court player likely to be apart of the fold and more so in the rotation, the question will arise if the team should trade their two-time All-Star in Isaiah Thomas—a guy no one would’ve envisioned becoming a franchise guy.

Thomas will be entering the final year of a 4-year, $27M contract and will make about $6.3M during the 2017-’18 season. The 5-foot-9 guard is entitled to a hefty contract as he approaches 30-years-old, and seeking the max shouldn’t be out of the question for him. The issue with giving him the max is it’ll hinder Boston’s cap flexibility as he and Al Horford will count as a majority of the salary cap.
Along with Thomas’ impending free agency creating an interesting complication for the franchise, defensive ace Avery Bradley will be primed for a payday in 2018 once his 4-year, $32M deal concludes. Thomas and Bradley are two of the key players for the Boston Celtics, and that isn’t the end of it. Marcus Smart could also be gone by 2018. Smart wasn’t supposed to be the team’s sixth man, Thomas was. Smart was viewed as being the franchise cornerstone. The tables really did turn with these two.
With Smart not reaching the heights people viewed for him coming out of Oklahoma State—mainly because of his lackluster jump-shot—his value around the league is interesting.
So many decisions will be made within the next year, and it all depends on how this summer and next season goes. If the guard the Celtics draft shows flashes of stardom coming off the bench, then why not trade an aging Thomas? Come to think of it, the future of the franchise hinges on this summer and next season. If no league altering deal happens and the team has the pick, then why keep Thomas, Crowder, and Bradley? Their assets are primed to dry up sooner rather than later, especially if they don’t flip their prospects and picks into superstar talents.
The worst location in the NBA is being in the middle, because how do you get good? Boston has been lucky with the Nets picks and others they’ve acquired but soon those picks will become prospects, and not all of them will be on the roster. Keep the prospects, then you’re in the building stage. Trade them, then you’re looking for veterans to win now. It’s a tough spot to be in, and time is running out for the Boston Celtics to solve the conundrum.