Career
Eastwood was drafted in the 5th Round, 91st overall by the Toronto Maple Leafs in the 1987 National Hockey League Entry Draft. He then played four seasons with Western Michigan University of the CCHA. He played 164 games for Western Michigan, scoring 69 goals and adding 80 assists for 149 points. His best season was his last one when he had 29 goals and 32 assists in 42 games.
In 1991, Eastwood made the jump to pro hockey.
He did not become an National Hockey League regular though until 2 years later. In 1995, Eastwood was traded to the Winnipeg Jets for Tie Domi.
This started a trend for Eastwood as he would then go on to play for many different teams. In his career he has played 783 National Hockey League games, scoring 87 goals and adding 149 assists for 236 points.
His best season came in 1999–2000, when he scored 19 goals and 15 assists for 34 points.
After his retirement in 2004, Eastwood was sought out by sports radio producers in the Ottawa area for his perspective on the National Hockey League. He currently co-hosts the Ottawa Senators post-game show with Scott MacArthur, and has appeared in radio commercials for restaurants in the Ottawa area.