One reason GM's like Ainge are collecting 1st round picks is due to expected "double draft" coming soon
The NBA has kind of let the cat out of the bag that they are willing to agree to the Players Association demand in the new CBA to allow pprospects to enter the league directly from high school. Typically it's a give and take thing in negotations and the league is now trying to "get something" for this concession, but it may be too late.
While lowering the 19-and-over draft age will be a significant part of the NBA/NBPA Collective Bargaining discussions, sources tell ESPN nothing has advanced on elimination of the “One-and-Done” rule.
If one-and-done is changed, it’s expected the starting date would be several years into the future; in part because of commitments already made by teams to trade future draft picks under the current framework of the 19-and-over system.
Reportedly the year that high school players will be allowed to enter the league is not imminent. So think somthing like 2026, 2027, or 2028. NBA people are calling that draft a "double draft" since it will have all the top freshman of the last of the one-and-done years and also all the top high school seniors (who would typically make up the top of the next draft).
So one can understand why some GM's like Danny Ainge and Sam Presti have been stockpiling 1st rounders for the mid to late 2020's. Would be quite the bit of insider trading if a GM knew the exact year that the "double draft" was going to take place.
The Boston Celtics own all their future first round picks with the exception of next year's (owed to the Pacers) and their pick in 2028 (which the Spurs own the right to swap). A lot can happen to teams' outlooks in six years and that is why Stevens mentioned after the Derrick White deal that giving up that pick swap was the kind of thing that keeps him up at night.
My opinion still stands, that though I like White as a player, I believe the Celtics overpaid for him. The team had already turned things around the prior month to the trade deadline and White didn't offer that much of an upgrade in my opinion to Josh Richardson to trade a 1st rounder and a future pick swap.
We should learn within the next year when this "double draft" will be. Also expect with a new TV deal for NBA contracts to get even crazier. Expect to see some guys making $75 million a year in the next CBA.