Ryan was a highly successfully jumps trainer during the period that spanned the end of World War II up to the early 1970's. In that time he accounted for the Champion Hurdle on three occasions, as well as the Gold Cup and the Grand National. He was also champion trainer five times between 1954 and 1967. He had a particular affiliation with the Schweppes Gold Trophy winning four times. It wasn't all sweetness and light though as after one win his licence was suspended for the remainder of the season after his winning horse had been deemed to have shown too much improvement compared to it's form during the rest of the campaign.