4 Biggest Milwaukee Bucks Trades

min read
Oscar Robertson shooting a layup for the Bucks during an NBA game in April 1971.
(Wikimedia Commons/Walter Iooss Jr.)
Anatoly Pimentel @AnatolyPimentel Nov 20, 2023, 1:09 AM
  • Here's a list of the biggest Milwaukee Bucks trades in franchise history.
  • Oscar Robertson leads the list of players Milwaukee received through trade.
  • Other notable players the Bucks acquired were Ray Allen, Khris Middleton, and Damian Lillard.

Giannis Antetokounmpo, who was drafted as the 15th overall pick in the 2013 draft, is the current face of the Milwaukee Bucks franchise. The “Greek Freak” revived the team’s excitement and has helped Milwaukee become one of the top title contenders in basketball odds. Due to his consistent MVP-level play, Antetokounmpo is one of the NBA players with a $200 million contract.

But selecting players through the draft was not the only formula for the Bucks’ success, as they were also part of multiple big-time trades. They were able to acquire superstars that greatly improved their chances of winning a title. Here’s a list of the top-four players Milwaukee secured via trade.

Oscar Robertson

The biggest trade that Milwaukee made happened occured in 1970, when they shipped Flynn Robinson and Charlie Paulk to the Cincinnati Royals (now known as the Sacramento Kings) for Oscar Robertson. It was shocking news around the league, as the “Big O” was the Royals’ superstar, and the Bucks immediately benefited from this big-time deal.

Robertson formed a big three in Milwaukee with Kareem Abdul-Jabbar and Jon McGlockin, and the trio delivered a championship in their first season together. The 6-foot-5 legendary playmaker played his last four seasons as a Buck before retiring in 1974. Robertson accumulated an average of 16.3 points, 7.5 assists, and 4.9 rebounds in 288 games for Milwaukee.

Ray Allen

The 1996 NBA Draft is one of the top draft classes of all time, but a rare draft pick to draft pick trade went down. Milwaukee’s fourth overall pick Stephon Marbury was traded to the Minnesota Timberwolves for their fifth overall pick Ray Allen and a first-round pick that was used to select Rasho Nesterovic. Allen went on to become one of the most prolific players in Bucks history.

In his six-and-a-half season as a Buck, the 6-foot-5 sharpshooter helped the franchise reach the postseason three times and as far as the Eastern Conference Finals in 2001, when they were one win away from the NBA Finals. Allen’s numbers from 494 games for Milwaukee were 19.6 points, 4.6 rebounds, and 3.8 assists. He also represented the team in three NBA All-Star Games.

Khris Middleton

In July 2013, Milwaukee finally moved on from their 2009 10th overall pick Brandon Jennings, as he was dealt to the Detroit Pistons for Khris Middleton, Brandon Knight, and Viacheslav Kravtsov. There were no significant expectations from these players, but Middleton found his home in Milwaukee and showcased his full potential.

The former Texas A&M standout formed an elite duo with Antetokounmpo and flourished under the system of coach Mike Budenholzer, and they claimed the best record in the league multiple times in the past decade. Middleton also became an important part of the championship team in 2021, as they beat the Phoenix Suns in the NBA Finals in six games. In 10 seasons for Milwaukee, “Khash Money” provided an average of 17.7 points, 5.0 rebounds, and 4.0 assists.

Damian Lillard

Milwaukee’s most recent blockbuster trade was the acquisition of seven-time NBA All-Star and multiple-time All-NBA member Damian Lillard from the Portland Trail Blazers in a three-team trade with the Phoenix Suns. The Bucks gave up Jrue Holiday, Grayson Allen, a future first-round pick, and a future pick swap to receive the “Dame Time.” The trade pushed through in September 2023 in the midst of Lillard’s trade request out of Portland.

The former sixth overall pick in the 2012 NBA Draft will form a new big three with two-time MVP Giannis Antetoukounmpo and Khris Middleton, as they are now the consensus favorites in the Eastern Conference. Lillard averaged 32.2 points (the third-most in the league), 7.3 assists, and 4.8 rebounds for the Blazers in the 2022-23 NBA season.

4 Biggest Milwaukee Bucks Trades

YearPlayer AcquiredTrade Details
1970Oscar RobertsonBucks received: Oscar Robertson / Royals received: Flynn Robinson and Charlie Paulk
1996Ray AllenBucks received: Ray Allen and Rasho Nesterovic / Timberwolves received: Stephon Marbury
2013Khris MiddletonBucks received: Khris Middleton, Brandon Knight, and Viacheslav Kravtsov / Pistons received: Brandon Jennings
2023Damian LillardBucks received: Damian Lillard / Blazers received: Jrue Holiday, DeAndre Ayton, Toumani Camara, 2029 first-round pick and pick swap / Suns received: Jusuf Nurkic, Nassir Little, Keon Johnson, and Grayson Allen

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About the Author

Anatoly Pimentel

Read More @AnatolyPimentel

Anatoly Pimentel is an NBA and MMA writer previously featured in ASEAN Sports, Asian Persuasion MMA, and Overtime Heroics MMA. He graduated from Adamson University with a B.A in Communication and is a Web Content Writer for BetMGM.

Anatoly Pimentel is an NBA and MMA writer previously featured in ASEAN Sports, Asian Persuasion MMA, and Overtime Heroics MMA. He graduated from Adamson University with a B.A in Communication and is a Web Content Writer for BetMGM.