Just for kicks, I'll throw in the name of Perrault. He finished first in the Big Cap, won the Hollywood Gold Cup, won the San Luis Rey (then GI Turf) defeating John Henry, and won the Arlington Million in 1:58 and change. He was pretty good on both surfaces.
It's tough to beat old John' though. He's still the only horse to win both the Santa Anita Handicap AND the Arlington Million twice. And in addition to his wins in the San Juan Capistrano, Oak Tree Invitational (3X), and NY's Turf Classic, he managed to throw in a victory in the Jockey Club Gold Cup just for fun.
I don't know about 50 years, but it's hard to think of a horse that was better on both surfaces in the last 35 or 40 years than John Henry.
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