A Kelly Olynyk-Boston Celtics reunion would be awesome (but it's next to impossible)

Adding former Celtic Kelly Olynyk to a currently thriving Celtics team would be a dream come true. Sadly, it seems pretty much impossible to do it without messing with the rotation's current makeup.
Cleveland Cavaliers v Boston Celtics - Game One
Cleveland Cavaliers v Boston Celtics - Game One / Adam Glanzman/GettyImages

Celtics faithful got quite some holiday cheer when NBA Insider Marc Stein reported via his Substack that the Celtics were among the teams interested in Utah Jazz big man Kelly Olynyk on Christmas Day.

"League sources say Boston is among the teams that is monitoring Utah's Kelly Olynyk in advance of a potential trade pursuit," Stein wrote. This is not the first time the Celtics have been linked to Olynyk since leaving Boston in 2017. They have had reported interest in reuniting with their former lottery pick dating back to 2021 when The Boston Globe's Adam Himmelsbach reported that Olynyk was one of their free agency targets. It didn't end there.

Heavy Sports' Steve Bulpett reported last February that the Celtics were among the teams interested in bringing back Olynyk, writing, "A source close to the Heat tells Heavy Sports the club is interested in a reunion with Kelly Olynyk — and that Miami isn’t his only suitor. The Celtics are also said to be looking at the possibility of re-acquiring the 6-11 floor-spacing big man, who spent his first four NBA seasons in Boston."

So, it's clear as day that Brad Stevens wants Olynyk back in Beantown, and why wouldn't he? Olynyk's having an awesome season as a floor-spacing seven-footer. Sure, his averages are down, which can be attributed to his minutes being cut down from having to share frontcourt minutes with Lauri Markkanen, Walker Kessler, and John Collins. However, Olynyk's shooting percentages are as good as ever, putting up 55/42/89 splits. Given Stevens' affinity for stretch bigs, Olynyk would be an awesome asset to have in the second unit. Given both his skillset and his experience in Boston, trading for him would make more sense than, say, Isaiah Stewart.

Best of all, Olynyk will likely be available. Utah's season is going nowhere, as they are 12-18 and are the No. 12 seed in the Western Conference. At 32 years old, Olynyk doesn't fit with their rebuild, and his services are better utilized on a team vying for a title, like, say, the Boston Celtics.

Alas, here comes the wet blanket. Completing a potential Olynyk trade without messing with the status quo is downright impossible. For example, trading Al Horford plus one of their vets' minimum players for KO would easily get a trade done, but it goes without saying that trading Horford for Olynyk would be a drastic overpay. Maybe the Celtics could throw Payton Pritchard in a possible deal, but why would the Celtics risk their guard depth to upgrade their sturdy frontcourt depth, and are the Jazz really willing to take Pritchard's poison pill contract?

From a financial standpoint, the Celtics could trade their end-of-the-bench pieces for Olynyk. Take this hypothetical trade, for example.

The hardest pieces to part with in a deal like this would be Kornet, who's been awesome as the Celtics' third big when they've called his name, and Walsh, who is the first infusion of youth the Celtics have had since Stevens took over as President of Basketball Operations. For someone as skilled and proven as Olynyk, trading that many pieces would be worth the risk. However, this also doesn't work because of the NBA's current Collective Bargaining Agreement. Celtics Wire's Justin Quinn referenced NBA capologist Eric Pincus when explaining why the Celtics can't make a deal like this.

TLDR: Because they have crossed the NBA's second tax apron, the CBA prevents the Celtics from combining multiple players signed to veterans' minimum contracts to acquire a more expensive player. So, unless the Celtics want to part with their more handsomely paid players, like Horford, an Olynyk trade won't be in the cards. Also, the Celtics can't aggregate anyone they would acquire with the Grant Williams TPE in an Olynyk trade because they would have to wait two months after acquiring someone to pull that off. That deadline passed on December 8.

There is another option for the Boston Celtics to get Kelly Olynyk, even if it's unlikely

With a trade likely out of the question, the Celtics' only hope for Olynyk would be to sign him following a potential buyout. The ex-Celtic could be a buyout candidate since his deal is expiring. However, given how cheap his deal is at $12.2 million, it could be easily acquirable by any team looking for another rotation big like Olynyk. More teams than usual are vying for the postseason, so the likelihood of Olynyk not being traded, knowing the current playoff environment, seems low. However, should the Jazz not find any takers, and if they feel it's not worth keeping the 10-year vet around, that's where the Celtics could swoop in.

Even though they are a second-tax apron team, the Celtics could sign Olynyk outright were he to be waived because his contract is just under the cutoff line for players they can add after a buyout with the non-taxpayer mid-level exception being $12,405,000. If the desire for a reunion is mutual between the two sides, he would give the Celtics much cushion to conserve both Horford and Kristaps Porzingis for the stretch run. Better yet, to have three reliable stretch bigs on the Celtics roster would make them even more of a matchup nightmare for opponents than they already are.

The question would be if Olynyk would like a role like that. More than anything else, Olynyk's primary focus should be on his next deal. While the Celtics would give him a role as a rotation player on a winner, lesser teams can offer him a more featured role than the Celtics could. A bigger role would help Olynyk's chances of getting another solid payday than playing for a winner would because it did just that two years ago. Despite being one of the league's worst teams, the Rockets opted not to waive Olynyk when they acquired him in 2021. Because they didn't have any better options, he then put up the best numbers of his career, averaging 19 points and 8.4 rebounds on 55/39/84 splits in 27 games.

What happened next? Olynyk got a nice fat deal with the Pistons the following summer. Now, he could potentially enter a similar predicament this season. Olynyk will turn 33 in April, so no one would blame Olynyk if he's primarily looking out for another long-term deal. The Celtics offering Olynyk a legitimate chance at a title is a heartwarming story in and of itself, but paying the bills may be more of a priority than uplifting audiences.

Olynyk's never been a special NBA player as much as he's been a rare breed. That's what's helped him earn as much money as he has despite hardly ever putting up gaudy numbers. The Celtics would become all the more bulletproof should they get their hands on him again. Sadly, from the looks of things, the odds of that happening aren't much higher than a Kyrie Irving reunion in Boston.