A five-time conference Coach of the Year and owner of the most wins in program history, Stephen Brennan is currently in his 18th season as head coach with a career record of 253-205. An assistant to former coach Serge DeBari for six years, Brennan has guided Babson to NCAA or ECAC Tournament berths six times during his tenure as head coach, including a trip to the Sweet 16 in 2002, an ECAC Championship in 2003, and another NCAA Tournament appearance in 2004. In 2002, Brennan was named the NEWMAC Coach of the Year, NEBCA Division III Coach of the Year, and NABC Northeast Region Coach of the Year. He then garnered his fifth conference Coach of the Year award in 2007.

A 1983 graduate of nearby Belmont High School, Brennan captained the Marauders and was a Middlesex League All-Star selection as a senior. Brennan matriculated at Bates College, where he was a four-year letter winner for the Bobcats, graduating in 1987. Following a year in private business, Brennan returned to his alma mater as assistant coach for one year before joining the Babson staff in 1989 in a similar capacity. A respected lecturer and director of the popular Babson basketball camp, Brennan received his master's degree in teaching from Tufts University in 1992. He currently resides with his wife, Samantha, in Natick, Mass.