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.
In January 2013, Hammond and Bucks owner Herb Kohl agreed to a three-year extension worth approximately $5.5 million. The Bucks have reached the NBA Playoffs twice during Hammond's tenure as General Manager.