DEAL AGREED AND COMPLETED: Milwaukee Bucks Have Officially Confirmed The Signing Of Boston Celtics Top Talented Star Jrue Holiday to Mega 5 Years Contract Worth $282 Million

The Miami Heat defeated the 2019-20 Milwaukee Bucks in the first round of the Bubble playoffs. They replied with a daring move, dealing for Jrue Holiday of the New Orleans Pelicans to team up with MVP Giannis Antetokounmpo and All-Star wing Khris Middleton.

The transaction paid dividends for the Bucks, who rode Holiday to the NBA Championship the following season. However, the Bucks paid a high price, sending numerous players and possession of five first-round picks, including unprotected firsts in 2025 and 2027.

That 2025 pick, in particular, went on quite the ride after the Bucks traded it to the Pelicans. A few years later, New Orleans traded it to the Portland Trail Blazers in exchange for CJ McCollum, but the move did not work out as well for them as it did for the Bucks. When the Blazers traded for Jerami Grant months later, the pick might have been conveyed.

Detroit traded up in the 2022 NBA Draft to get Memphis center Jalen Duren, sending the Bucks’ pick to the New York Knicks. Finally, when the Knicks acquired Mikal Bridges last summer, they included the 2025 Milwaukee pick, which is currently held by the Brooklyn Nets — though it might be moved again before all is said and done.

The pick is unprotected, so there were times this season when it appeared the Nets might be hanging onto a gem. The Bucks began the season 1-6, and by January, their record had only improved to 17-16. Then Antetokounmpo became a freight train, Damian Lillard regained his groove, and the Bucks went 31-18 the rest of the way to finish 48–34.

Even after the season finished, it remained unclear which pick the Bucks were sending to the Nets. Two other teams finished with 48 victories, and the NBA decided to settle such ties with a simple coin flip or random drawing — which they did Monday afternoon.

The Bucks’ Jrue Holiday trade had another pick completed.
While a few other coin flips had a greater influence, such as the Phoenix Suns giving the Houston Rockets the ninth choice, the Bucks’ selection was also determined. Surprisingly, all three teams who finished 48-34 owed their picks to different teams. The Memphis Grizzlies “won” the drawing, and the Washington Wizards will receive selection No. 18 from the Marcus Smart contract dump. The Golden State Warriors “lost” the drawing and will send selection No. 20 to the Miami Heat as part of the Jimmy Butler transaction (a bit more significant than the Smart salary dump).

The Milwaukee Bucks fell squarely in the center, thus they will send the Brooklyn Nets the 19th pick in the 2025 NBA draft.

Given that the choice was unprotected and their season had gotten off to such a shaky start, this is not a bad result for Milwaukee. They would have like to send the 29th or 30th choice following a dominating season and a No. 1 seed, but it was not in the cards. Their squad is elderly and ill-fitting, and the pairing of Lillard and Giannis hasn’t taken off as the club had intended. And this is why the future appears to be quite unpredictable.

From 2024 to 2027, the Bucks will either surrender their choice to another team or be exposed to a swap, all as a result of the Jrue Holiday trade. Damian Lillard has taken over for Holiday, who has long since left. The Boston Celtics, who won the title last year and are expected to win it again this year, have begun their holiday season. The Bucks are nowhere near that level, and a Game 1 defeat at the hands of the Indiana Pacers brings their demise even closer.

Will the Bucks end up trading a lottery pick to another team in the coming seasons? The Pelicans own the swap for next season, and if the selection is excellent in 2027, the Pelicans will keep it (or send it to Atlanta). And Milwaukee hasn’t quit trading future draft selections; they still owe a first and two swaps from 2028-2030 from the Lillard trade.

However, one piece of the puzzle is now in place. The Bucks will send the 19th pick to Brooklyn, passing via New Orleans, Portland, Detroit, and New York, and live to fight another day.