Hi, y'all -- just posted this info to the Thoroughbred Champions forum, which has been debating the Step Lightly pic.
This morning, searching the Corbis stock photography (online) archive, what did appear but Ms. Step Lightly #19 labeled "Man o' War with Jockey Clare [sic] Kummer." That takes the misidentification at least back to early 1938, because part of the caption reads: "On March 29, Samuel J. [sic] Riddle, owner of Faraway Farm, where Big Red is now spending his last days, will throw a 21st birthday party for the greatest horse of them all." As you can see from the jockey and owner name mistakes -- not to mention the horse herself -- a confuuuuuuuused person assigned to cover Man o' War's birthday celebration may've put this mess together. ;>