What should the Celtics do with three 2020 first-round picks?

With a glut of young players and an open title window, having three first-rounders can be difficult to navigate. Danny Ainge has become a premier asset manager, and this year becomes no different. The Celtics want to win, and they have a meaningful core of win-now players that can take them to the promised land.

Nothing about the position Ainge and his staff are in is easy. The Celtics could have over $140 million in committed salary to 14 players next season. That doesn’t include two-way players and 2019 second-round picks Tacko Fall and Tremont Waters, both of whom will pushing for roster spots, too.

The more layers you peel back, the more complex this picture becomes. For a win-now team, the Celtics currently have seven rookies employed: Fall and Waters, Javonte Green and Vincent Poirier, and former first-rounders Romeo Langford, Grant Williams and Carsen Edwards on guaranteed contracts that can run up to 2023. The kick-in of Jaylen Brown’s four-year, $115 million extension beings next year, likely propelling the C’s into the luxury tax and handcuffing their ability to chase veteran pieces in their prime. That number could be offset by Gordon Hayward opting out of his $34.2 million player option for next year, but that’s not only unlikely, but could steal long-term funds away that’ll be budgeted for an upcoming Jayson Tatum max contract.

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Painting this entire picture accurately is key in understand just what the Celtics can do with their draft picks. Because of guaranteed contracts to first-round picks, this isn’t a situation where the Celtics can just draft three players and build their team without salary repercussions. Boston likely has 14 guaranteed deals for next year before the draft starts. Do the math and three picks quickly illuminates the “no vacancy” signs in the Garden. Our own Keith Smith has broken this down in nuance.

We also have to contextualize how this draft is layered with talent, especially in relation to where Boston’s picks likely fall. Currently, the Celtics would receive picks #14 (from the Memphis Grizzlies), #26 (their own) and #30 (from the Milwaukee Bucks), in addition to the 46th pick later in the second round. This draft is relatively weak on franchise-transcendent stars, and even thinner with high-ceiling prospects reliable enough to round out the lottery.

In essence, this might be the worst draft to try and trade up or trade out of. The 30th pick this year holds far less value than in next year’s stacked 2021 class. Consolidating 26 and 30 to move up to the mid-teens likely doesn’t net a high-impact player.

Ainge is surrounded by rocks and hard places. The draft is all about finding the future and getting high production on the low cost of rookie-scale deals. But he must field a contender constructed to win immediately, with few roster spots to manipulate.

So what should their draft strategy entail, if Ainge is to simultaneously thread the needle on these two important areas?

Try this mantra: play one, develop one, stash one.

Let’s work backwards on this. The stash part of the equation has two elements. The first is the traditional way we think of “draft-and-stash” with international players. The Celtics could take a prospect who needs time to develop, ascertain his rights for when he’s ready to come to the NBA, and avoid taking a cap hit in 2021.

Another way to look at it: trade back for a pick in a future year. While likely losing equivalent value (meaning the 17th pick now won’t net the 17th pick next year), moving back would allow the Celtics another weapon to consolidate and move up next year. It solves the problem of what to do with the size of the roster as well. Whether through swapping picks into a future draft or keeping someone overseas, it’s hard to envision the Celtics not taking this path with at least one of their selections.

The development prong is a way for the Celtics to take a prospect they feel will eventually be the best player but isn’t ready to fulfill an immediate role. Putting positions aside, the Celts likely can afford to hide one long-term prospect on their roster. Not all seven rookies from this year will return, and expectations for any newcomer next year should be low to begin with. Without Summer League or a full four months to prepare for action, most franchises could opt for stability and continuity. Boston shouldn’t need two rookies to play significant minutes.

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Of course, the pursuit for Banner 18 in 2021 could be aided by any of this draft class’ more ready-to-go prospects. Rookies regularly make large impacts on contending teams; just ask Grant Williams. If Boston keeps all three picks, using one on a plug-and-play model makes a great deal of sense.

What are Boston’s needs that can be addressed through the draft? One might be the backup point guard spot, which could be vacant with Brad Wanamaker as a restricted free agent. Another could be an additional wing shooter from the 3-and-D archetype who can thrive off-ball.

Even if you buy this “play one, develop one, stash one” viewpoint, there’s a whole side of this equation left untouched: which player do you draft first?

Much of that is dependent on how the board shakes out on draft night. If a highly-coveted international prospect is around at #14, how can Ainge pass him up knowing the value a stash player has for their roster concerns? Can the Celtics find players they trust to play immediately at #26 or #30? If not, do they stash two guys? All this is tied to the continued improvement of last year’s picks like Romeo Langford and Carsen Edwards. If Ainge isn’t optimistic that either can step into a role next year, he’ll run out of room for future projects on the shelves.

Of course, everything could change if “Trader Danny” decides he wants to flip some of these young players (currently on the roster or their 2020 selections) to make a large splash. But ingest your mock drafts wisely. There are more important factors at play for this roster than simply taking the three best picks or fits available. There’s an entire puzzle for the front office to manipulate that likely requires some shake-up, trades, or cutting bait with some intriguing projects they’ve already undertaken.