On April 24, 2010, it was announced that Hammond had won the annual NBA Executive of the Year Award, the first time a Bucks executive had ever won the award in the team's history. Hammond was credited with building a Bucks team that went from 34 to 46 victories in one season, including a return to the playoffs for the first time since 2006. He also was responsible for several moves he made before the 2009-2010 season, such as drafting Brandon Jennings and bringing in veteran John Salmons in a trade. Both of them played key roles in the Bucks' 2009-2010 campaign.
The Bucks have reached the NBA Playoffs twice during Hammond's six-year tenure as General Manager, yet have failed to win a playoff series. During one of those two playoff appearances, they had a losing regular season record (38W - 44L) and were swept in the first round, losing each of the four games by an average of 15 points. During Hammonds' stewardship the Bucks have posted 199 wins against 277 losses, a winning percentage of .418. The 2013/14 edition of the Bucks, the franchise's 46th, and Hammond's most recent team, posted a franchise all-time worst record of 15 wins and 67 defeats, a winning percentage of .183, as well as featuring the worst attendance in the NBA. In January 2013, Hammond and Bucks owner Herb Kohl agreed to a three-year contract extension worth approximately $5.5 million. Kohl sold the team in May of 2014.