Busting Brackets
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NBA Draft 2020: Biggest winners and losers from the Draft Lottery

NEW YORK, NEW YORK - JUNE 20: (L-R) NBA Draft prospects Coby White, Zion Williamson, NBA Commissioner Adam Silver, Ja Morant and De'Andre Hunter stand on stage with NBA Commissioner Adam Silver before the start of the 2019 NBA Draft at the Barclays Center on June 20, 2019 in the Brooklyn borough of New York City. NOTE TO USER: User expressly acknowledges and agrees that, by downloading and or using this photograph, User is consenting to the terms and conditions of the Getty Images License Agreement. (Photo by Mike Lawrie/Getty Images)
NEW YORK, NEW YORK - JUNE 20: (L-R) NBA Draft prospects Coby White, Zion Williamson, NBA Commissioner Adam Silver, Ja Morant and De'Andre Hunter stand on stage with NBA Commissioner Adam Silver before the start of the 2019 NBA Draft at the Barclays Center on June 20, 2019 in the Brooklyn borough of New York City. NOTE TO USER: User expressly acknowledges and agrees that, by downloading and or using this photograph, User is consenting to the terms and conditions of the Getty Images License Agreement. (Photo by Mike Lawrie/Getty Images) /
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BOSTON, MASSACHUSETTS – JULY 17: Kemba Walker and Enes Kanter (Photo by Tim Bradbury/Getty Images)
BOSTON, MASSACHUSETTS – JULY 17: Kemba Walker and Enes Kanter (Photo by Tim Bradbury/Getty Images) /

Loser: Boston Celtics (Specifically, Danny Ainge)

If Celtics executive Danny Ainge knew that when he dealt Jeff Green to the Memphis Grizzlies in exchange for Tayshaun Prince’s expiring contract and a protected future first-round pick way back in January 2015, that said pick would ultimately convey as a late-lottery selection a year after the Grit ‘n’ Grind era ended, he’d probably be quite pleased with himself. He could even see it as a heist, considering that the Grizzlies chose to offload Green to the Clippers a mere 13 months later.

But when considering that Ainge’s previous strategic maneuver — a trade-back with the Philadelphia 76ers that saw Jerry Colangelo give up a future Sacramento first-rounder to move up to select Markelle Fultz first overall in the 2017 draft, whereas Boston picked Jayson Tatum third — ultimately saw the Kings’ random 2018 surge cause their premium draft pick to land at 14, it’s hard not to view the Memphis pick’s similar slide to No. 14 as an unmitigated letdown.

More than anything, Boston’s front office was dreaming of a scenario where Memphis skyrocketed at the lottery and see their pick vault into the top four, leaving their 2021 first-rounder to convey to Boston in what is perceived as a top-heavy draft class featuring the likes of Cade Cunningham, Jonathan Kuminga, and Jalen Green.

Instead, the Celtics saw a potentially valuable trade chip flame out and land at No. 14 once more, whereas the Grizzlies head into next season primed for another trip to the lottery with a chance to add another cornerstone next to Ja Morant and Jaren Jackson Jr.

There are worse things than owning what amounted to a free first-round pick, but the alternative — a shot at a real franchise-altering star next year — is a painful miss. There are still projectable role players and potential starters available at the backend of the lottery (namely Tyrese Maxey, Devin Vassell, Cole Anthony, among others), but this is still a clear victory for the Grizzlies, even though they don’t have a first-rounder this year.