Billionaire L.A. family claims racism at elite Westside country club

An empty golf course is seen at Hillcrest Country Club in Los Angeles.
An empty golf course is at Hillcrest Country Club in Los Angeles in this May 2020 file photo.
(Patrick T. Fallon / Bloomberg via Getty Images)

The venerable Hillcrest Country Club, a historically Jewish organization for residents once banned from other elite L.A. social clubs, is being sued by the son of a onetime Bel-Air billionaire who alleges racial discrimination and civil rights violations.

Matthew Winnick, a 42-year-old Jewish man, claims in court papers he was denied membership into the private club because his wife and their children are of “Hispanic heritage.”

His attorneys, brother Alexander Winnick and Anthony Trujillo, label Hillcrest a “150-acre plantation in the heart of Los Angeles,” where its more than 500 members are shielded from the true racial makeup of the city and nepotism leads to those who don’t meet the socially acceptable requirements for membership.


The Winnicks are the sons of the late billionaire Gary Winnick, who rode the dot-com boom to become one of L.A.’s richest people. Gary Winnick was a longtime member of Hillcrest, which has been popular with movie moguls, business tycoons and a host of celebrities, including George Burns and Danny Kaye.

Club attorney Lyne Richardson said the lawsuit “is entirely without merit,” adding: “Hillcrest Country Club intends to defend itself fully.”

The Hillcrest Country Club, considered the leading predominantly Jewish country club in Los Angeles, has changed its bylaws and is in the process of admitting its first regular women members, its president said Monday.

April 28, 1987

Bryan Freedman, an attorney for Hillcrest’s president and two other board members named in the lawsuit, also scoffed at the allegations, calling them frivolous.

“The late Gary Winnick, a long-term member, showed up at the ‘racist’ club regularly until the time of his passing,” Freedman said in an email to The Times. “When Gary recently passed away, his family (which includes the plaintiff, Matthew Winnick, and his brother, Alex Winnick, the lawyer in this case) asks to host the memorial at Hillcrest, the same place they are claiming is the ‘discriminatory’ club.

“Sounds to me like ... what really seems to upset them [Matthew and Alex] is that they could not get into Hillcrest despite the alleged nepotism policy.”

The lawsuit argues that the club is violating the state’s civil rights law and, because it gets funds from nonmembers, is also subject to a 1987 Los Angeles ordinance barring discrimination at such facilities.


Second gentleman Doug Emhoff, husband of Vice President Kamala Harris and an avid golfer, has had a membership at Hillcrest. Winnick’s lawsuit opens with a quote from the vice president: “In times like this, silence is complicity.”

The plaintiff says in the suit that he was granted access to the club as an intermediate member for many years and paid for that privilege. In February 2023, he says he applied for full membership. According to the lawsuit, he met all three criteria: 100 hours of community service, giving 5% of his available cash flow to charity and being deemed socially acceptable as a person of good moral character.

The following month, Winnick and his family attended a birthday party with Jason Kaplan, a top Hillcrest board member and now club president. Winnick alleges in the lawsuit that Kaplan, who knew his wife and children were Latino, yelled ¡Cállate! — “shut up” in Spanish — across the table at him.

According to the lawsuit, Winnick was “alarmed, confused, embarrassed by Jason Kaplan’s rude interruption” and later confronted him. Kaplan told him, “You want to mess with me,” the lawsuit states.

In April, Winnick wrote to Hillcrest’s membership director “detailing his concerns about racial discrimination” and interference with his application and said he believed he was being treated differently because of his wife’s “Hispanic descent.” Besides his interaction with Kaplan, Winnick alleged that previous club President Michael Flesch had blocked his participation in a club sub-committee.

Kaplan, Flesch and Brad Fuller, another member of the Hillcrest board, are named in the lawsuit. Kaplan, a well-known capital fund manager, is accused of making “racist remarks” and committing an unspecified sexual assault, which is not detailed in the lawsuit. Flesch is accused of using his position in the club to get his son membership — despite his son’s acknowledged history of drug addiction. And Fuller, a longtime Hollywood producer behind movies such as “The Purge” and “The Texas Chainsaw Massacre,” has “built his career on creating pornographic and violent films that glorify murder and reinforce harmful stereotypes,” the lawsuit alleges.

An L.A. Times exposé — and in one instance, Gloria Allred quite literally exposing sex discrimination — led the Jonathan Club, the California Club, the Friars Club and others to become less exclusive, if not less expensive.

April 4, 2023

Winnick says that instead of investigating his concerns, the club informed him on May 1 he had not satisfied the requirement for membership and terminated his application.


At a hearing at Hillcrest to discuss his membership, Winnick said that Trujillo, who is Latino and his brother’s law partner, was denied entry to the club despite the presence of six other current or former attorneys.

Flesch insisted during the hearing that Hillcrest has many members of Latino descent, according to the lawsuit.

Winnick, however, argues in the lawsuit that Hillcrest is overwhelmingly white, pays an embarrassing low property tax — only about a quarter of a million dollars on property that otherwise would be taxed at around $70 million annually — and has no desire or incentive to change.

“Hillcrest is a racial aristocracy, subsidized by the city,” the lawsuit alleges.

About eight blocks from where I grew up there was a big country club with high walls.

Aug. 12, 1990

The suit includes social scientist Malcolm Gladwell’s analysis that L.A.’s country club golf courses have used special carve-outs that have allowed them to avoid millions of dollars in property taxes and haven’t been reassessed in decades because, despite changing membership, the clubs claim to have not changed ownership.

Winnick alleges the only minorities at most country clubs are the predominately Latino staff. The lawsuit also notes that Hillcrest did not admit women until 1987, the year Los Angeles adopted a new law addressing discrimination by private clubs with more than 400 members that receive money from nonmembers.

“There is a group of people who run Hillcrest as their personal fiefdom, violating the basic principles of fairness and equity,” Alex Winnick said in a statement to The Times about the lawsuit. “Change is overdue.”


Freedman told The Times the three Hillcrest members named in Winnick’s suit will pursue their own legal action. “Make no mistake,” Freedman said, “Brad Fuller, Jason Kaplan and Michael Flesch will file a lawsuit for malicious prosecution.”