Indiana Guaranteed the Brogdon Deal
Indiana acquired Malcolm Brogdon in a July 2019 sign-and-trade after Milwaukee signed him to the new contract. The Pacers sent a future first-round pick and two future second-round picks rather than risk an offer-sheet process on the restricted free agent. The club's own account explained the logic: waiting could have tied up cap space while Milwaukee decided whether to match, with other free agents disappearing in the meantime. Indiana paid real draft capital, but it secured the 26-year-old guard immediately and built its backcourt plan around him.
Brogdon Produced, Then Indiana Recycled the Asset
Brogdon started all 146 regular-season games he played for Indiana across three seasons. His scoring rose from 16.5 points per game in 2019-20 to 21.2 in 2020-21, and he remained a 19.1-point scorer in his final Pacers season. Availability kept the tenure from becoming an A-level outcome by itself, but the exit preserved value. In July 2022, Indiana sent Brogdon to Boston for Aaron Nesmith, Daniel Theis, three additional players and a 2023 first-round pick, extending the original 2019 investment into the next roster cycle.
Milwaukee Turned the Compensation Into Useful Flexibility
The Bucks did far better than simply losing a restricted free agent. Indiana's 2020 first conveyed at No. 24, the R.J. Hampton slot, and that draft asset was routed through the four-team Jrue Holiday transaction that brought Holiday to Milwaukee. One Brogdon-derived second-rounder also went to Orlando in the draft-night deal that moved Milwaukee to No. 45 for Jordan Nwora. The three-pick return therefore supplied assets the Bucks could reuse around a championship-caliber roster, which is why the canonical B+ grade is stronger than a consolation-prize evaluation.
Both Teams Extracted More Than One Layer of Value
The deal worked because the teams were solving different problems. Indiana wanted Brogdon badly enough to remove restricted-free-agency uncertainty and got three seasons of starting guard production before trading him for another package. Milwaukee chose not to match the contract but converted his departure into a first, two seconds and a trade exception; the first later became part of the Holiday transaction. Brogdon was the best immediate asset and Indiana kept value alive after moving him, but Milwaukee's return had genuine downstream use. The gap is narrow rather than punitive.
Final Verdict
Slight Pacers Edge — Indiana A-, Milwaukee B+. The Pacers paid a first-round pick and two second-round picks to secure Malcolm Brogdon, then received 146 starts across three seasons before moving him to Boston for a package headlined by Aaron Nesmith and a 2023 first-round pick. Milwaukee did not lose Brogdon for nothing: the No. 24 pick from Indiana became part of the asset flow in the Jrue Holiday deal, and another incoming second helped Milwaukee acquire the No. 45 slot used on Jordan Nwora. Indiana gets the higher grade for landing the best player and preserving later trade value, while Milwaukee's asset conversion keeps the result close.