After his graduation from law school, D'Alessandro worked on the successful re-election campaign for Republican Congressman Rick Lazio in 1996. From 1997 to 2004, D’Alessandro next worked for Professional Management Associates, a Washington, DC-based sports agency, where he represented NBA and international basketball players.
He was hired by Golden State Warriors basketball chief and Hall of FamerChris Mullin in 2004 to join the Golden State Warriors as the director of basketball operations. Golden State promoted D’Alessandro to assistant general manager in 2006. D’Alessandro became known for his strong analytical skills and expertise in the NBA salary cap. In 2010, D’Alessandro was recruited away by the newly hired GM of the Denver Nuggets, Masai Ujiri, to work for him as his advisor. In 2012, he was promoted to Vice President of Basketball Operations. He helped the Nuggets to a franchise record 57 regular season wins that year. After Ujiri left for the Toronto Raptors, D’Alessandro was initially seen as the front runner for the general manager position of the Nuggets.
Sacramento Kings
On June 17, 2013, he was hired as the new general manager of the Sacramento Kings by new majority owner Vivek Ranadive. D'Alessandro pledged to aggressively pursue deals as the Kings GM and followed through on that with three major trades in the first five months of his tenure, including a 7-player trade with his former boss Ujiri in Toronto. But the promising start quickly devolved, and his tenure in Sacramento was ultimately regarded as "a mess". D'Alessandro was responsible for getting rid of Isaiah Thomas, a favorite player of both the fans and coach Michael Malone, and who has since become an NBA All-Star with the Boston Celtics. That move was followed up with his insistence upon the midseason firing of head coach Michael Malone, in favor of Tyrone Corbin as a stepping stone to George Karl. The firing of Malone was universally criticized at the time, and with the subsequent firings of both Corbin and Karl, has since solidified itself as one of the most catastrophic head coach firings in modern NBA history. Furthermore, throughout D'Alessandro's time with the Kings, he developed a tendency to leak negative stories to the media about members of the Kings organization, including DeMarcus Cousins, Isaiah Thomas, Michael Malone, and owner Vivek Ranadive, in an effort to further his own personal agendas. Ultimately, this was a significant factor in an upper management shakeup that resulted in his tenure as GM coming to an end.
Return to Denver
Upon being relieved of his duties with the hiring of Vlade Divac as Vice President of Basketball Operations, he left the Sacramento Kings on 06/10/2015 to accept a front office position with the Denver Nuggets
On June 10, 2017, it was announced that D'Alessandro would take on a new position as assistant general manager for the Orlando Magic.
Personal
D’Alessandro resides in the Orlando area with his wife Leah, daughter Kate and son Benjamin. He met his wife while working on the 1996 Lazio campaign and she played a strong role in encouraging him to pursue his dream of running the operations of basketball franchises.
