In 1987 Ailshie was contacted by Larry and Carolyn Peters, a couple who owned Oil Stock, the previous year's World Grand Champion Racking Horse.
[3] The Peters thought Oil Stock could do so and wanted Ailshie to take over his training from Jackie Barron, who had ridden him the previous year.
[3] With the Peters' support, Ailshie rented a new 21-acre facility with option to buy and expanded it to ultimately house 55 horses in two barns.
[3] Ailshie won his fourth World Grand Championship in 1998, riding The Finalizer for the Clyde Creech family.
Her son Brandon, Kenny's grandson, was at age 4 the youngest person to ride unassisted in the Racking Horse World Celebration.
[4] In 2017, Alshie's grandson Brandon won the Racking Horse World Grand Championship on Helter Skelter.