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Meet Billie Holiday’s 3 Husbands Including Jimmy Monroe Who Was Described as ‘Worst Type of Parasite You Can Imagine'

Stephen Thompson
Sep 11, 2021
04:30 A.M.
Billie Holiday will always be remembered for her melodious voice and musical talent. While she is celebrated even in death, many are unaware of her struggles with alcohol and drug abuse. Inside the singer's personal life.
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Eleanora Fagan, popularly known as Billie Holiday, was born on April 7, 1915. She became a jazz music icon in the 1930s and 1940s and was greatly celebrated for her delivery and exceptional vocal style.

Holiday's happy and successful career was only the opposite of her personal life. She struggled with substance abuse, which ultimately led to her downfall, and she finally died, aged 44.

Photo of Billie Holiday circa 1970 | Photo: Getty Images

Photo of Billie Holiday circa 1970 | Photo: Getty Images

Before her demise, Holiday was married three times. Holiday tied the knot for the first time with acclaimed hustler Jimmy Monroe in 1941. However, Monroe had a negative impact on the singer as reports had it that he was an opium smoker and an excessive drinker.

He was once described as "the worst type of parasite you can imagine" by a federal prosecutor. A year after the couple walked down the aisle, Monroe was caught smuggling drugs into California.

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Billie Holiday during her onstage performance at the Newport Jazz festival on July 6, 1957. | Photo: Getty Iamges

Billie Holiday during her onstage performance at the Newport Jazz festival on July 6, 1957. | Photo: Getty Iamges

The "hustler's" bad habits continued to rub off on Holiday, and she began using drugs, which eventually led to their divorce. Shortly after her divorce, Holiday got romantically involved with a trumpet player named Joe Guy.

The pair eventually tied the knot, and while they were married, Holiday continued using drugs with her husband. In October 1945, Holiday lost her mother, and to ease her grief, she turned to alcohol and more drugs.

Although Holiday was separated from McKay, they were still legally married at the time of her death.

Billie Holiday (1915 - 1959) performing at the Club Downbeat in Manhattan. | Photo: Getty Images

Billie Holiday (1915 - 1959) performing at the Club Downbeat in Manhattan. | Photo: Getty Images

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Her substance abuse caught up with him in May 1947 when she received a one-year sentence after being arrested and charged with heroin possession. After leaving prison in 1948, Holiday quit drugs, but she got back into the bad habit shortly after.

Holiday was arrested again for a similar crime, but this time she was acquitted. Holiday's marriage to Joe soon ended, and she continued with her music career. While at it, she found love in the arms of Louis McKay.

Billie Holiday in court during contract lawsuit in Los Angeles, Calif., 1949. | Photo: Wikimedia Commons By Los Angeles Times photographic archive, Public Domain

Billie Holiday in court during contract lawsuit in Los Angeles, Calif., 1949. | Photo: Wikimedia Commons By Los Angeles Times photographic archive, Public Domain

As his woman, McKay abused drugs as well. In 1956, the pair were arrested for possession of narcotics, but that did not stop them from tying the knot the following year. Holiday and McKay's relationship was a complicated one.

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McKay was often described as an abusive husband and used his wife to advance his name. Later on, the pair separated, and Holiday moved into a New York apartment after McKay lost her money in risk property speculation.

Billie Holiday photographed in 1945. | Photo: Wikimedia Commons, Public Domain,

Billie Holiday photographed in 1945. | Photo: Wikimedia Commons, Public Domain,

While living alone with her dog, Holiday's drug abuse alongside her alcohol intake increased, and in May 1959, she was hospitalized. She was placed under arrest after a nurse found drugs by her bedside. She finally died on July 17, 1959, in the hospital.

Although Holiday was separated from McKay, they were still legally married at the time of her death. He inherited her music royalties and estate when she died, and when McKay died, his wife, Bernice, and his son, Louis, inherited a third of Holiday's estate.

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Billie Holiday and her dog Mister Dog, backstage in 1946. | Photo: Wikimedia Commons, Public Domain

Billie Holiday and her dog Mister Dog, backstage in 1946. | Photo: Wikimedia Commons, Public Domain

Holiday's funeral was held at St Paul the Apostle Roman Catholic Church in New York City. Jazz legends like Benny Goodman and Mary Lou Williams were in attendance.

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