NHL. Despite leading the defense in scoring for a second consecutive year, he recorded a career-low six goals for 32 points in 81 games. On the eve of the beginning of the free agency period, on July 1, Liles was re-signed to a new four-year contract with the Avalanche on June 30, 2008. In the 2008–09 season, Liles rebounded offensively to again top all Avalanche defensemen in goals with 12, and ranked fourth on the team in points with 39 as the struggling Avalanche finished 27th in the NHL, its worst-ever finish under the Avalanche name. Transitioning into a senior role for the Colorado defense, Liles scored his 50th career goal against the Toronto Maple Leafs on January 29, 2009, to become only the fifth defender in Quebec/Colorado history to achieve the feat. Hampered by a re-occurring shoulder injury midway through the 2009–10 season, Liles also struggled with returning to form and was a healthy scratch for a brief period of time for the first time in his NHL career. Despite playing in a career-low 59 regular season games for 31 points, he still led the resurgent youth-laden Avalanche team in defenseman scoring for a fourth consecutive season. To begin the 2010–11 season, Liles made NHL and franchise history when he recorded an assist in a 4–3 overtime loss to the Vancouver Canucks on October 26, 2010, giving him assists in nine consecutive games to open the season. Despite the Avalanche failing to qualify for the 2011 playoffs, Liles accumulated a career-high 40 assists in 76 games played. Toronto Maple Leafs On June 24, 2011, Liles was traded by the Avalanche to the Toronto Maple Leafs in exchange for a second-round pick in the 2012 NHL Entry Draft. He scored his first goal as a Maple Leaf in a game against the Columbus Blue Jackets. On January 25, 2012, Liles signed a four-year, $15.5 million contract extension with the Maple Leafs. On October 1, 2013, after being waived by the Maple Leafs, he was assigned to the team's AHL affiliate, the Toronto Marlies. He was later recalled to the NHL on October 28, sent back on November 15, then recalled again on December 6. Carolina Hurricanes On January 1, 2014, Liles was traded to the Carolina Hurricanes, along with Toronto prospect Dennis Robertson, in exchange for defenseman Tim Gleason, just minutes before the former was scheduled to play for the