 Smith spent parts of three seasons in Toronto before being traded to the Edmonton Oilers on March 3, 1999, during the 1998–99 season.When the Oilers' team captain Doug Weight was later traded to the St. Louis Blues, Smith's strong leadership tendencies resulted in his being handed the captaincy, where he would ultimately match Wayne Gretzky as the longest-serving captain in Oilers history at five seasons, wearing the "C" from 2001 to 2007, excluding the 2004–05 NHL lock-out in which the 2004–05 season was cancelled.Smith captained the Oilers to a largely unexpected run to the 2006 Stanley Cup Finals, in which they faced the Carolina Hurricanes, another dark horse team.