A Complicated Life May Have Led to Deegan's Death

On the evening before Mr. Deegan's death, he was reportedly in the company of a woman at the Starlight Hotel and Bistro in Santa Monica. The waiter who served the couple dinner that evening and on several prior occasions identified the lady as the actress, Jayne Montgomery. Ms. Montgomery divorced her husband, director Cliff Styles, two years ago and remains unmarried. The Hollywood duo reportedly met on the set of Too Many Angels, which Mr. Styles directed. The film became a box office hit in 2012, and the couple married shortly after. Although nominated for Performance by an Actress in a Supporting Role in the movie, Jayne Montgomery did not win the award. In 1999 Clifford Styles received an Oscar for Best Director for his debut film, Out of Sorts, starring Jeanette Foley, with whom Mr. Styles purportedly had an affair.

In 2019 Jack Deegan's wife, Emily (Holt) Deegan, sued him for divorce on the grounds of infidelity and won her case in court. Mr. Deegan allegedly had relations with a young waitress he met at a burger joint in El Segundo six weeks before the divorce filing. Emily hired a private detective to record and document the illicit activity at a Marriott Hotel. Her lawyer produced the findings in court as incontrovertible evidence of infidelity committed by Jack Deegan. Although the evidence had no bearing on the court's ruling in the case, since California is a no-fault divorce state, the court did decide to grant Emily the divorce.

Jack remained unmarried for the brief remainder of his life. When he realized he needed extra money to make the alimony payments to his ex-wife, he decided to delve into real estate. Some of the proceeds he made from various property transactions were questionable, as previously reported by the press. According to the IRS, Mr. Deegan failed to fully disclose income from the proceeds of some of the properties. Specifically, the 100-acre parcel in Palmdale, California, for which he received nearly a half-million dollars.

Jack Deegan made numerous trips to Las Vegas, where he accumulated an insurmountable debt in a futile effort to pay off the money he owed to the IRS and his ex-wife.

With finances heading toward disaster, Jack tried to dissolve his troubles in alcohol. When liquor wasn't enough to erase his misery, he began using drugs – first marijuana, then cocaine, crystal meth, and finally, heroin. Somehow, he was able to keep his reckless lifestyle of alcohol and drug abuse separate and hidden throughout most of his remaining professional legal career.

He continued to represent perpetrators such as prostitutes, pimps, and drug dealers until the end of his career, a mere three weeks before he was found dead. One of his most notorious clients was MS-13 member, Enrique Cortez. Cortez also happened to be Jack's most recent drug dealer. The apparent conflict of interest forced Jack to end his career, leading to his removal from the California Bar Association.     

Story and Cover Illustration Copyright © 2021 by Michael DeFrancesco