The story goes that in late September 1938, Bill Kyne, of the Bay Meadows race track, was at Roberts-at-the-Beach and said to Shorty Roberts that horses could not swim. Shorty's response was that his horse Blackie could swim across the Golden Gate. Kyne initially wagered $5,000 that this could not be done. The final wager was $1,000, and the plan was for 12-year-old Blackie to swim from Lime Point in Marin County to San Francisco.
At one point, the SPCA got wind of the plan and, worried about danger to Blackie, convinced the government to forbid Roberts to launch the horse from Marin County. "So Shorty's friend, A. P. Paladini, used his large fishing boat troller with a sling and net, and lowered Blackie down into the water from the side of the boat," according to Al Sportorno.
Shorty accompanied the horse on the swim. According to Al, there were no wetsuits, so Shorty covered his body with grease. In addition, Shorty couldn't swim. He wore a life preserver and held onto Blackie's tail.The swim took 23 minutes and 15 seconds. See the short film about the swim here.
This story was written by by Lorri Ungaretti, but I wanted to republish because I thought it was interesting.