O'Toole was the head coach of the Fairfield Stags men's basketball team coach from 1998 to 2006 where he compiled a 112–120 record. He was named the Metro Atlantic Athletic ConferenceCoach of the Year in 2004. O'Toole's best season came in 2002-03, when the Stags lost the MAAC championship game to the Manhattan Jaspers but earned a berth in the NIT. While at Fairfield, he was also recognized by the state of Connecticut for implementing a reading program that reached more than 65,000 kids, designed to promote the importance of academics and athletics. O'Toole had been an assistant coach for the Fordham Rams, Army Black Knights, Iona Gaels, Syracuse Orange, Duke Blue Devils, and Seton Hall Pirates. In 2013, O'Toole became the director of basketball operations for the Syracuse Orange and went to the Final Four. The next season, he went out west with the Stanford Cardinal as an assistant to Johnny Dawkins. With the Cards, he went to the Sweet Sixteen in 2014 and won the NIT in 2015. After his stint with the Cardinal, he moved across the bay to work for the rival. In 2016, he took a job under Cuonzo Martin with the Golden Bears of Cal Berkeley. Now O’Toole is back on the east coast working with Jeff Capel at the University of Pittsburgh helping to coach the Panthers.
Playing career
O'Toole played at the collegiate level for Fairfield University. He became only the fourth player in school history to be named captain twice. O'Toole was a member of the Fairfield teams that won two straight MAAC titles and reached the NCAA tournament in 1986 and 1987. He was named co-MVP following his junior season after averaging 11.6 points per game. O'Toole earned the Patrick Burke award in 1983 and 1984, given by the University to a player who shows the most hustle and determination. He received the Jerry Lademan award, presented to a Stag for academic success. And he earned Fairfield University Male Athlete of the Year as a senior. In 2017 O'Toole was inducted into the Fairfield University Hall of Fame. At Archbishop Stepinac High School, he averaged 21 points and seven rebounds per game under Gene Doris, currently the Director of Athletics at Fairfield University. He was an All-Archdiocese pick and New York Post second team All-CHSAA pick.
Education
O’Toole received his B.A. from Fairfield University in economics/political science and his M.B.A. in finance from Fordham University.