Private Life
Now famous, Merrill thoroughly enjoyed his celebrity and loved the nightlife and hobnobbed with both the famous and infamous. Although earning a good salary, he habitually was broke due to gambling. He had become a fixture at the parties of the rich and famous, and it was at one of these that he met Toby Wing, a chorus girl who became a movie star, appearing in 52 features and shorts. The two married in Tijuana in 1938, but her parents objected to this sort of marriage, so they were married a second time at the home of Sidney Shannon, an early Eastern Air Lines investor. His marriage finally turned around his financial woes and he became devoted to his new wife. Merrill was 22 years Wing's senior, and shortly after their marriage she met Bob Hope who joked, "Toby it's nice to see you and I'm glad to see you brought your father along." According to Wing, Merrill never forgave Hope for the insult.
After a Broadway run, Toby retired from show business the next year, and the couple moved to Miami, where Merrill flew the Eastern Air Lines Miami to New York runs with occasional flights to South America.
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