A five-time state champion, Bob Keino enjoyed a remarkable running career for the Maroons and still holds two RHS track records, 4:09.35 in the 1,600 meters and 9:02.73 in the 3,200 meters. He won back-to-back Meet of Champions titles. He was undefeated in distances from 800 meters to 3,200 meters both his junior and senior years. He was first team All-State six times, two each his cross country, indoor track and outdoor track, and first team All-County and All-League nine times.

He was the Penn Relays Athlete of the Meet his junior season when he ran a 4:08 1,600 anchor in the distance medley relay to take Ridgewood from 16th to third place and also turned in a 1:52 in the 800 meters. He won the Penn Relays 3,000 race his senior year. He was state champion in the 3,200 meters his junior and senior seasons, 3,200 meters indoors as a junior and in cross country both his junior and senior campaigns. He won the Footlocker Northeast race at Van Cortlandt Park in New York and finished fourth in the Footlocker Nationals in San Diego, Calif. He was All-America and All-Pac 10 running for the University of Arizona. He finished college at Rutgers but did not compete for the Scarlet Knights. He ran a 3:53 mile after college. The son of two-time Olympic gold medalist Kip Keino of Kenya, Bob did some sailing off the coast of Kenya in the Indian Ocean and became interested in sailing. After working for Catholic Charities in London, he enrolled in the UK Sailing Academy on Isle of Wight, England for certification on a luxury or racing yacht.