The Celtics are easy to mock because of Brad Stevens’ whiz kid Democratic strategist vibes and the reverent, awed-dummy tones announcers slip into when Gerald Green scores an easy lay-in off a crisply executed out-of-bounds set; and because Marcus Smart is a junkily solid defender whose ability to draw the odd fourth quarter charge on the back end of a three-for-nine shooting night gets New Englanders talking like he’s Dennis Johnson; and because Kelly Olynyk is Marmaduke with a jumper; and because you just don’t get how many little things Al Horford does to help this basketball team win games; and because Danny Ainge very nearly makes eight brilliant trades per year and gives himself credit for all of them. There’s a top-down Catholic school attitude in Boston that’s cultish and apple-polishing and smug, and since this isn’t the mid-80s and they’re hardly top of the heap, it makes them kind of a joke. In the middle of their annual playoff demolition, you can catch a sizable slice of the NBA Internet overdosing on schadenfreude.

The thing is, though: the Celtics are a pretty well-run shop, even if Ainge’s prowess is overstated. (That draft history, outside of Avery Bradley, is rough.) The infamous Brooklyn trade that netted Boston three first-rounders and a pick-swap in 2017  working out as well as it has can be attributed to luck—Kevin Garnett and Paul Pierce immediately flopped and Deron Williams fell off hard—as much as foresight, but it was still a smart move. Isaiah Thomas was a steal when the Celts traded for him, and this past season he took his game to a level no one quite expected him to. Despite Jae Crowder’s defensive slippage over the past couple of years—why is anyone’s guess; he’s only twenty-six—he’s on one of the league’s thriftier contracts. In the post-Doc Rivers era, Ainge, like the similarly sainted Daryl Morey before James Harden came to Houston, has set his franchise up to compete without making any foolish all-in trades or signings that would endanger their long-term flexibility. Basically, the Celts have been competitive and entertaining without kidding themselves too hard with regard to the Eastern Conference belonging to LeBron James.

In keeping with that approach, Ainge understands that acquiring Gordon Hayward alone this offseason isn’t going to put the Celtics where they want to be. Hayward is one of the better forwards around and would help Boston significantly in terms of giving them another player alongside Thomas who can create his own shot, but he’s more likely to enhance the Celtics’ pretty-goodness than catapult them into greatness. Ainge is also in the market for Paul George, who’s almost definitely leaving Indiana this summer, and who’s a superior talent to Hayward but perhaps isn’t franchise fortunes-altering either.

This is a obvious thing on its face, but it’s not something many NBA execs would be bold enough to try: what if the Celtics got them both? The logistics aren’t simple. Ainge would have to agree to terms with the Pacers, then get Hayward to believe him that George is coming, finalize Hayward’s (presumably max) contract, and finally come back for George. There also might be some cap-clogging flotsam jettisoning to be done given that the soft salary cap is going to settle around $99 million, about nine million bucks below where the league expected it to be at this time last year. The Hayward-then-George maneuver is especially tricky because the Cavs are working frantically to ship Kevin Love somewhere—Denver, perhaps—for assets that can be flipped for George, and the Jazz, who put together a nice season and have an interesting young roster, are trying to shore up their starting point guard spot in order to entice Hayward to stay in Utah. Ainge is working against a lot, here: the interests of one free agent, three front offices, and time.

Plausibility of the double-move aside, it’s the only thing the Celtics can do this offseason that would put them in the championship hunt. Who knows if Hayward, George, Thomas, and Horford would be enough to overcome the Cavs, let alone the even-more-stacked Warriors, but it gives the Celts a legitimate shot at a title, and trying to make it happen is a testament to Ainge’s grip on reality, which has always been his greatest asset. The Brooklyn picks have allowed him to compete and rebuild simultaneously over the past few seasons, and he has never pushed too strongly toward one pole or the other. This would be him finally capping the team out and going for broke. It’s not a perfect opportunity, but it’s a promising one that took some serious patience to arrive at.

If there’s been a legitimate recent critique of Ainge, it’s that he’s trigger-shy and seems to fetishize his own value-multiplying trade wizardry in lieu of assembling an actual team. Drafts can only be properly evaluated three or four years after they happen, but passing on a consensus stud like Markelle Fultz to pick up an extra lottery pick and select an offense-first Dukie in Jayson Tatum looks, in the moment, like a typically too-cute Ainge gambit. Right or wrong, the man likes complexity. But at the very least, Ainge is clear-eyed about where the Celtics are in the league hierarchy at any given time, and what needs to be done to put them near the top. Many execs focus myopically and ultimately self-destructively on improving their roster without answer the question to what end? Ainge knows what he’s after, and that’s what makes him good at his job.