Mike Sullivan took an interesting path to head coach of the Pittsburgh Penguins. Originally drafted by the New York Rangers in 1987, Sullivan made his NHL debut with the inaugural San Jose Sharks in 1991. He played in San Jose for three seasons and went on to play with the Boston Bruins, Calgary Flames and Phoenix Coyotes before calling it a career.
His first head coaching gig was relatively brief. He took over the Bruins in 2003 and led Boston to a division title (but a first round playoff exit). After the lockout, the Bruins finished dead last in a spectacularly strange year of NHL hockey.