Leogrande was the 2006 winner of the United States National Amateur Criterium Championships, and spent two years with the infamous Rock Racing team, having turned professional in 2005 with US domestic squad Jelly Belly–Pool Gel.
Leogrande vigorously contested the charges brought against him by the United States Anti-Doping Agency (USADA), but was suspended for two years after a three-member arbitration panel concluded he had used EPO.
In 2017 Leogrande was suspended by USADA for a further 8 years after testing positive for multiple prohibited substances following a win at the Dana Point Grand Prix.
Under the guidance of then team-manager and confidant Joseph M. Papp, Leogrande promptly won the points classification at the 2007 Redlands Bicycle Classic, where he also finished second in the stage two criterium.
[5] In January 2008 Leogrande made headlines when he was revealed to be the anonymous rider filing a lawsuit against USADA, seeking to prevent the testing of his B-sample from a urinalysis taken at Superweek the previous year, which was thought to contain evidence of EPO.
USADA refrained from testing the backup sample and the suit was dismissed – but the anti-doping agency still charged the rider with a doping violation.,[8] Later in the year, Leogrande filed a defamation claim against former Rock Racing soigneur Suzanne Sonye.