Dorothy Sherwood

Sherwood was freed on parole on December 27, 1939, after serving three years and three months at the Westfield State Farm (Bedford Hills Correctional Facility for Women) in Bedford Hills, New York. The Salvation Army employed her doing clerical work in one of its institutions. Sherwood was allowed to visit her 11-year-old daughter, Dorothy May, who resided in Newburgh.

Sherwood, 27, pleaded temporary insanity during her trial for the drowning of Jimmy in January 1936. The jury recommended mercy when it convicted her of first-degree murder. The jury foreman mentioned that she had led a hard life. Trial Judge Jonathan D. Wilson was compelled by New York state law to sentence her to die in the electric chair at Sing Sing. Two defense psychiatrists maintained that Sherwood was insane while two prosecution psychiatrists testified to the contrary. In 1936 all first-degree murder convictions were reviewed by the New York Court of Appeals.

The United States War Veterans Association circulated petitions days later urging Governor Herbert Lehman to grant Sherwood an unconditional pardon. She won an appeal for a new trial. The Court of Appeals set aside the first-degree murder conviction on July 8, 1936. She pleaded guilty to the first-degree manslaughter the following September 2 and received a six-to-fifteen-year sentence. She was then 28.

Sherwood drowned two-year-old Jimmy in Moodna Creek in Newburgh, on August 20, 1935. The case was exceptional, being the only first-degree murder case involving a woman in Orange County, New York history until then.

Sherwood was born in St. Louis, Missouri. She was the third child of Thomas Caskey, a Scotch-Irish foundry worker and his wife Florence Caskey. Her father was married six times and Sherwood was the daughter of his third wife. One of her older siblings died at eighteen months and another at five years of age. Sherwood's mother died when she was nine and she was placed in an orphanage. Salvation Army work, in 1925, followed her period in the orphanage. As a lassie, she wore a red-ribboned bonnet. In this endeavor, she sang gospel hymns in six southern cities for approximately three years. From this job, she moved on to dance in burlesque.

Dorothy O. Sherwood, née Caskey (born February 7, 1908, date of death unknown) was a burlesque dancer and Salvation Army worker who was convicted of first-degree murder for killing her two-year-old son.