Liffiton began his junior career with Aylmer Blues in the OHA-B before he was selected in the 16th round, 326th overall, in the 2000 Ontario Hockey League priority selection by the Plymouth Whalers. Joining the Whalers in the 2001–02 season, and developing as a physical stay-at-home defenseman, Liffiton recorded his best season statistically in 2002–03 with 5 goals for 16 points in 64 games to help the Whalers reach Western Conference finals against the Kitchener Rangers. He was subsequently drafted 63rd overall in the 2003 NHL Entry Draft by the Colorado Avalanche. In his final year with Plymouth in 2003–04, Liffiton\'s rights were included in a trade by the Avalanche, along with Chris McAllister, to the New York Rangers in exchange for Matthew Barnaby and a third round selection in 2004 (Denis Parshin) on March 8, 2004.\n', '

Signing an entry level contract with the Rangers on July 29, 2004, he began his professional career with Rangers ECHL affiliate, the Charlotte Checkers, before moving up to American Hockey League affiliate, the Hartford Wolf Pack for the majority of the 2004–05 season. In the 2005–06 season he continued to play primarily with Hartford and finished second on the Wolf Pack with 169 Penalty minutes. Towards the end of the season, the Rangers were hit with injury on the blueline and David made his NHL debut playing a solitary game against rivals the New York Islanders, registering 2 penalty minutes, in a 3-2 defeat on April 11, 2006.\n', '

He played in two further games in the 2006–07 season with the Rangers, including his first NHL fight against the Boston Bruins\' Jeremy Reich, but again remained entrenched as a physical force among the Wolf Pack blueline amassing 189 penalty minutes in 72 games. In his fourth season within the Rangers organization in 2007–08, Liffiton was limited to only 21 games with the Wolf Pack suffering post-concussion symptoms that kept him sidelined for the majority of the year.\n', '

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