Career
He played college basketball at DePaul University. In 2005, Diener was diagnosed with stomach cancer originated by Crohn"s disease. He underwent two surgical operations that took him off the court for one year.
In June 2006, Diener signed his first professional contract with Ignis Castelletto Ticino of the Italian Second Division.
Thanks to a good season there, the following year he signed for Orlandina Basket in the Italian First Division. After becoming the top scorer of the Italy"s highest league, in February 2008 he signed with Montepaschi Siena.
During that season in Siena, Diener contributed to the team"s victory of the Italian championship and a 3rd-place finish in the Euroleague. In October 2008, Diener signed a one-year deal with Scandone Avellino where he had again the chance to play in the Euroleague.
In July 2009, Diener signed a two-year deal with Teramo Basket.
During his stay in Abruzzo, Drake enjoyed great success confirming himself as one of the best players in the Italian league and the main contributor to Teramo"s remaining in the top division. In June 2012, he re-signed with Sassari for one more season. In July 2013, he again re-signed with Sassari, this time for two years.
On March 16, 2014 Diener scored 44 points against Reyer Venezia Mestre making his career high
He was also named the Lega Basket Serie A Most Valuable Player of the 2013-2014 season. In June 2014, he left Dinamo Sassari.
On July 23, 2014, Diener signed with Pallacanestro Reggiana and was released on June 30, 2015. On August 23, 2015, Diener signed with Computer-assisted instruction Zaragoza in the Spanish Liga ACB. On December 29, 2015, he parted ways with Zaragoza after averaging 6.1 points per game in ACB.
Diener suffered from Crohn"s disease.
During his 2 years in Teramo he earned the nickname of "Il Drago" (the Dragon) due to the similar sound of his first name to the Italian word.