Plain Sailing's international career spanned almost a decade and several top riders. He won team gold at the 1967 Pan American Games and team silver in the 1968 Olympic Games with Michael Plumb, team silver at the 1972 Olympic Games with Bruce Davidson, and team gold at the 1974 World Championships at Burghley with Don Sachey.

"Sammy" was a bay gelding, about 16.2 hands, by an Irish stallion named Walter Serpent and believed to be out of an Irish mare. Owned by Mr. and Mrs. Raymond Firestone when he was competing, Sammy was a strong individual, a very powerful, forward going horse, and as Don Sachey said, "As honest as the day is long about jumping and had a very clear opinion about how things should be done. He was a tough ride and strong, but you could really trust him to jump. Given his competitive record, he was obviously tough as nails to have had such a vast international career and it speaks highly of his soundness and mental toughness."

On the ground, Sammy had a special relationship with his groom and facility manager, Patrick Lynch. As Sachey put it, "One never got the impression he was overjoyed to be brushed, tacked up, handled. It was more that he tolerated it. He was much more experienced and much smarter than me during our time together and I am certain he was fully aware of the advantage that he had! There were a handful of horses like Sammy from the mid-1950s through the mid-1970s that possessed the ability to do a number of international competitive cycles and truly enabled the U.S. to develop the momentum to actually hire a great coach and move us on to the success at the 1974 World Championships. Sammy was a big part of that."