But considered to be Milligan’s best galloper was Carael Boy, a gelding (by Bluebird’s Irish-bred import Free Flyer) which won 20 races and had 11 placings for almost $1 million in prizemoney through the 2000s. A cups specialist, Carael Boy’s wins included eight stakes races, among them the Hawkesbury, Newcastle, Wyong and Liverpool Cups, as well as the 2001 AJC Villiers Stakes-G2.