Eastwood played in the NHL for seven teams, Toronto Maple Leafs from 1991 to 1995, Winnipeg Jets from 1994 to 1996, Phoenix Coyotes during the 1996–97 NHL season, New York Rangers from 1996 to 1998, St. Louis Blues from 1997 to 2003, Chicago Blackhawks during the 2002–03 NHL season and the Pittsburgh Penguins during the 2003-04 NHL season. He retired in 2004 and currently co-hosts the Ottawa Senators post-game show with Scott MacArthur.