Bob was a catcher with Elmwood Giants for 10 years, and won the Manitoba Juvenile crown in 1951. Bob umpired in Winnipeg midget, juvenile, and junior leagues. President of Manitoba Junior Baseball League, 1962-65. Picken acted as the Chairman of national junior tournament in Winnipeg in 1965, was a member of the 1967 Pan Am Games Baseball Committee and broadcasted the Pan Am medal games over Metropolitan Radio Network. Bob also Broadcast the Winnipeg Whips games in the International League in 1969 for CJOB. Bob was Manager of the 1999 Pan Am Games baseball committee, and media section.