Celtics have picks to take a swing … but when?

Celtics have picks to take a swing … but when? originally appeared on NBC Sports Boston

Championship windows are never promised and the Boston Celtics absolutely have to operate with an urgency when it comes to putting the most talented pieces around a core of Jayson Tatum and Jaylen Brown.

But it’s also clear that, after the Celtics overhauled some of the complementary pieces of their team this offseason and stocked up on draft assets in the process, Boston is positioned for one more big swing of the bat.

President of basketball operations Brad Stevens must time that swing up.

Stevens utilized a first-round pick acquired in the Marcus Smart trade to shuffle back and acquire five second-round picks on draft night. The team ultimately selected Arkansas wing Jordan Walsh at No. 38 — and signed him to the parent roster on Thursday — while emerging with four more second-round picks (one in each of the next four drafts).

After acquiring two more second-round picks (and a future second-round pick swap) as part of a Grant Williams sign-and-trade swap on Wednesday, the Celtics now have at least 13 picks in the next five drafts, including all of their own first-rounders and the Warriors’ 2024 first-round pick (top 4 protected) next year.

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That puts Boston in the conversation for any disgruntled player that hits the trade market. The name du jour, of course, is Damian Lillard as he tries to steer his way to South Beach. The Celtics, with their collection of draft assets and tradable salaries, can get in the conversation for any star player that becomes available.

The question: Do you push all-in for Lillard, who turns 33 in July? Given the cap crunch already looming with hopes of locking up Jayson Tatum and Jaylen Brown on supermax deals, can you afford to carry Lillard and a contract that has 2 years and $93 million remaining?

Every summer it feels like at least one star player yearns for a new home. More stars could desire a relocation by the February trade deadline.

From this vantage point, it’s important that the Celtics make the most of what could be the only swing they get during the prime of Tatum’s career. If the Celtics could entice the Blazers with a package that doesn’t include Jaylen Brown, it’s undeniably intriguing to think of a team that features Tatum, Brown, Porzingis, and Lillard.

But is that the best long-term play? What happens if a younger star shakes free further down the road?

We can debate whether the Celtics got better this offseason after moving on from Smart and Grant Williams, all while acquiring Porzingis. Stevens can still tweak the roster before the season tips in October. But it’s rather undeniable that, even as currently constructed, the Celtics are still atop the conversation among title favorites. Porzingis adds a highly skilled player alongside Tatum and Brown that could raise the ceiling of Boston’s playoff rotation.

We get it. Patience isn’t easy. The wait for Brown’s supermax deal has tested that with all of Boston’s antsy fan base. But it simply feels like the Celtics have avenues beyond Lillard that might bolster the roster, whether that’s a big swing on another disgruntled star or simply making a big-splash deal at the 2024 trade deadline.

Second-round picks aren’t very sexy. At least until you consider the buying power they have harnessed recently.

At last year’s trade deadline, center Jakob Poeltl got dealt to Toronto in a deal that included a future first-round and two second-round picks. Boston had interest in Poeltl but might have been scared off by the draft assets that would have needed to pry him free. Poeltl was an also impending free agent, though the big man signed back with Toronto this summer on a four-year, $80 million deal.

Last month, Bradley Beal and his no-trade clause powerplayed their way to Phoenix in a deal that featured salary matching (Chris Paul and Landry Shamet) along with four future first-round pick swaps and six second-round picks.

Pick swaps are undeniably risky and the Celtics already have one out there with the Spurs able to swap in 2028. But if you’re confident the core of your team will keep you competitive for the half decade, it can be a worthy dice roll.

Will Luka Doncic be content to ride it out in Dallas with Kyrie Irving re-signed to a long-term deal (there’s only so much that Williams can help in that instance)? Will Joel Embiid remain happy in Philadelphia as James Harden plots his future? Will Giannis Antetokounmpo stay content as the Bucks age?

Stevens has to balance all this while pondering what comes next. Would it be better to hunt a superstar on a more team-friendly deal that could be paired with the bulky salaries of the Jays and Porzingis? Does Boston have to ponder its own core after this season, when extensions for both Porzingis and Brown should begin.

Even while acquiring Porzingis, the Celtics have restocked their draft assets in the Smart and Williams transactions. They have at least put themselves in the conversation for another eyebrow raising deal moving forward.

The question for Stevens: When does he take that swing?