Chára was drafted in the third round, 56th overall, by the New York Islanders at the 1996 NHL Entry Draft. He would spend his first season in North America with the Western Hockey League (WHL)'s Prince George Cougars, who subsequently selected Chára in that year's CHL Import Draft. Chára spent four seasons with the Islanders organization, becoming a reliable, stay-at-home defender in a primarily defensive role. He earned a reputation as a tough player to play against – intimidating, physically strong and a punishing hitter who could, on occasion, fight. His physical strength also gave him a very hard slap shot, which seemed to improve each season, although Chára was never deployed in an offensive role as an Islander.