The 2019-20 Milwaukee Bucks were punked in the Bubble playoffs by the Miami Heat, losing in the first round. They responded with a bold swing, trading for New Orleans Pelicans star Jrue Holiday to pair with MVP Giannis Antetokounmpo and All-Star wing Khris Middleton.
The deal paid off for the Bucks, who rode the Holiday acquisition all the way to an NBA Championship the following season. Yet the price was not cheap; the Bucks sent multiple players and control of five first-round picks, including unprotected firsts in 2025 and 2027.
That 2025 pick in particular embarked on quite the journey once the Bucks sent it to the Pelicans. New Orleans sent it to the Portland Trail Blazers in the CJ McCollum trade a couple of years later, a deal that did not work as well for them as the Holiday deal did for the Bucks. The pick was then a potential option to convey when the Blazers traded for Jerami Grant months later.
Detroit traded up in the 2022 NBA Draft to take Memphis center Jalen Duren and in the process sent the Bucks' pick to the New York Knicks. Finally, the Knicks included the 2025 Milwaukee pick when they added Mikal Bridges last summer, and it is held by the Brooklyn Nets at the current moment -- although it could certainly be traded again before all is said and done.
The pick is unprotected, so there were moments this past season when it looked like the Nets could be holding onto a gemstone. The Bucks started the season 1-6, and even by the time January rolled around they had only climbed to 17-16. Then Antetokounmpo turned into a freight train and Damian Lillard found some of his rhythm and the Bucks went 31-18 the rest of the way to finish 48-34.
Even once the season ended, however, it was not clear what pick the Bucks were sending to the Nets. Two other teams also finished with 48 wins, and the NBA chooses to settle such ties with a simple coin flip or random drawing -- and they did so Monday afternoon.
The Bucks' Jrue Holiday trade had another pick finalized
While a handful of other coin flips were more impactful, including the Phoenix Suns sending the Houston Rockets the ninth pick, the Bucks' pick was finalized as well. Interestingly, all three teams that finished 48-34 owe their picks to other teams. The Memphis Grizzlies "won" the drawing and will send pick No. 18 to the Washington Wizards from the Marcus Smart salary dump. The Golden State Warriors "lost" the drawing and will send pick No. 20 to the Miami Heat from the Jimmy Butler trade (a bit more impactful than the Smart salary dump).
The Milwaukee Bucks landed right in the middle, and therefore will be sending the Brooklyn Nets the 19th pick in the 2025 NBA Draft.
Given that the pick was unprotected and that their season got off to such a rough start, this is not a bad outcome for Milwaukee. They would certainly rather be sending the 29th or 30th pick after a dominant season and a No. 1 seed, but that was not in the cards. Their roster is aging, ill-fitting and the combination of Lillard and Giannis has not taken off as the organization surely hoped. And that's why the future is looking extremely uncertain.
From 2024 to 2027 the Bucks are either sending their pick to another team or are vulnerable to a swap -- all from the Jrue Holiday trade. Holiday, of course, is now long gone, replaced by Damian Lillard. Holiday now starts for the Boston Celtics, who won last year's title and are a favorite to win it again this year. The Bucks are nowhere close to that level, and a Game 1 demolition at the hands of the Indiana Pacers only brings their doom that much closer.
Will the Bucks end up sending a lottery pick to another team in the next few seasons? The Pelicans own swap right next season, while if the pick is a good one in 2027, the Pelicans will keep it as well (or it may be sent to Atlanta). And it's not as if Milwaukee stopped trading future draft picks, as they owe a first and two swaps from 2028-2030 from the Lillard trade.
One piece of the puzzle, however, has now been locked into place. The Bucks will send the 19th pick to Brooklyn, via New Orleans, Portland, Detroit and New York, and live to fight another day.