Career
Gaddy was a highly sought after recruit for Washington: he was ranked the Number. 2 point guard in the class by Entertainment and Sports Programming Network behind John Wall and was a McDonalds All American in 2009. His collegiate career got off to a slow start as a backup to Venoy Overton and Isaiah Thomas.
As a sophomore, he moved into the starting lineup and averaged 8.5 points and 3.8 assists before an Anterior Cruciate Ligament tear in January 2011 ended his season.
Gaddy improved those numbers to 8.1 points and 5.2 assists as a junior. He led the Huskies to two National Collegiate Athletic Association tournament berths.
As a senior, he averaged 11 points and 3 rebounds per game. After going undrafted in the 2013 National Basketball Association draft, Gaddy joined the Charlotte Bobcats for the 2013 National Basketball Association Summer League.
On September 23, 2013, he signed with the Bobcats, but he was later waived on October 10.
On November 1, 2013, he was selected by the Iowa Energy in the second round of the 2013 National Basketball Association Development League Draft. His rights were then traded to the Santa Cruz Warriors on November 5, and then the Maine Red Claws on November 6. In 46 games for Maine in the 2013-2014 season, he posted averages of 9.0 points, 5.0 assists and 3.2 rebounds per game, while shooting.420 from three-point range.
He had the fourth triple double in Red Claws history on March 2 when he recorded 23 points, 11 assists and 10 rebounds against the Austin Toros.
Gaddy joined the New Orleans Pelicans for the 2014 National Basketball Association Summer League and averaged 5.2 points and 3.2 assists in five games. On July 30, 2014, he signed with Italian team Virtus Bologna for the 2014-2015 season.
In 33 games for Virtus, he averaged 7.3 points, 3.0 rebounds and 3.7 assists per game. On May 26, 2015, he signed a two-year contract extension with the club
He played a supporting role behind Kyrie Irving.
In five games, Gaddy posted averages of 5.0 points and 2.8 assists in 13.4 minutes per game.