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1900s diving horse attraction - photo
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I would think after 2 or 3 times the horse was having fun and no problem getting him to jump.
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When I was a child in Atlantic City A lady rode the horse off the tower into the water.
I think they dove into a tank but it appeared as tho they were going into the ocean.
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The lady who rode the horse off the tower depending on which year you are referring to. in the early days 1924 was Leana Carver
later Senora Webster dove with the hores red lips and in an accident was blinded but continued to jump until 1942 Senora was only 15 when she took her first dive in 1924 she lived until 2003 a book and a movie was made about her diving career the book A Girl and Five Brave Horses, the movie Wild Hearts Can't Be Broken, staring Gabrielle Anwar.
https://en.wikipedia.org/wiki/Diving_horse
