Kammala jumla mai zuwa: Liffiton ya fara aikinsa na matasa tare da Aylmer Blues a cikin OHA-B kafin a zaɓe shi a zagaye na 16, 326th gaba ɗaya, a cikin zaɓin fifiko na 2000 na Ontario Hockey League ta Plymouth Whalers. Shiga cikin Whalers a cikin 2001-02 kakar, da kuma ci gaba a matsayin jiki zama-at-gida defenseman, Liffiton ya rubuta mafi kyau kakar statistically a 2002-03 da 5 a raga ga 16 maki a 64 wasanni don taimakawa Whalers isa yammacin taron karshe da Kitchener Rangers. Daga bisani an rubuta shi a matsayin na 63 a cikin 2003 NHL Entry Draft ta Colorado Avalanche. A cikin shekararsa ta ƙarshe tare da Plymouth a 2003-04, an haɗa haƙƙin Liffiton a cikin kasuwanci ta Avalanche, tare da Chris McAllister, zuwa New York Rangers a musayar Matthew Barnaby da zaɓin zagaye na uku a cikin
2004 (Denis Parshin) a ranar 8 ga Maris, 2004.