Political Notes: Trans leader Middleton regains CalPERS oversight board seat

One of California’s more well known transgender leaders is once again serving on a prominent state oversight panel as she continues to adjust to life out of public office. At the same time, former Palm Springs councilmember and ceremonial mayor Lisa Middleton is remaining politically active.

Last year, Middleton, 72, opted to run for higher office rather than to serve again on the City Council of the Southern California LGBTQ retirement and tourist mecca. But the Democratic politico lost her bid for a state Senate seat in last November’s election.

Due to her stepping down from her council seat, Middleton also had to resign in February from the California Public Employees Retirement System Board of Administration on which she had served as a representative for local government elected officials since 2019. Governor Gavin Newsom (D) had appointed her that May to the oversight body for the nation's largest public pension fund, known as CalPERS, and tasked with overseeing the administration of the fund’s investments.

Wednesday, September 10, Newsom reappointed Middleton to it, this time as an insurance industry representative. The 13-member board also is responsible for setting policy and overseeing the administration of retirement and health benefits on behalf of California public employers, and their active and retired employees. (The position does not require state Senate confirmation and comes with a $100 per diem.)

In an Instagram post Middleton wrote she was “honored” to have Newsom’s confidence in her ability to again provide oversight for CalPERS. Her appointment came in time for the board’s meetings taking place Monday, September 15, through Wednesday.

“Governor Newsom is unwavering in his commitment to our two million public servants and their families; and in ensuring that our cities, counties, school districts and state can afford the benefits and promises we have made,” wrote Middleton, a former Bay Area resident. “For 95 years, CalPERS has kept our promises. I am well aware of my fiscal responsibility. I look forward to working with colleagues, CalPERS staff, and the people of California to ensure CalPERS keeps its commitments to every generations of public servants.”

From 1974 to 2010 Middleton had worked for the State Compensation Insurance Fund. Her positions through the years included senior vice president of internal affairs, San Diego district manager, and claims/rehabilitation manager.

“We welcome Lisa back to CalPERS and look forward to the experience and perspective she will bring in service to our 2.3 million members,” stated CalPERS Chief Executive Officer Marcie Frost. “We have seen firsthand how Lisa’s commitment to public service, both as a city leader in Palm Springs and a former board member, will be invaluable to our mission to provide retirement security and quality health care benefits to those who serve California.”

A native Californian, having grown up in East Los Angeles, Middleton graduated from UCLA in 1974 with a bachelor's degree in political science and received a master's in public administration from the University of Southern California in 1979.

She moved to San Francisco in 1994 while working for State Fund. It was at that time that she came out as transgender and later served on the San Francisco Human Rights Commission's LGBT advisory committee.

Between 2001 and 2004, Middleton served on the board of the San Francisco-based health clinic for lesbians, bisexual women, and transgender individuals now known as Lyon-Martin Community Health Services. She and her wife, Cheryl O'Callaghan, had moved to Belmont on the Peninsula until relocating to San Diego in 2004 for work.

Made history in Palm Springs
They eventually relocated to Palm Springs, and Middleton’s election to her council seat in 2017 made her the first transgender person elected to a non-judicial office in the Golden State. She had hoped to become the first trans member of the state Legislature last year.

While that did not come to pass, Middleton had been floated as a possible candidate for a congressional seat in 2026. Speaking to the Bay Area Reporter last month, Middleton declined to discuss what conversations, if any, she had had about becoming a U.S. House candidate.

Instead, she praised the candidacy of gay entrepreneur and trained economist Brandon Riker, whom she endorsed to represent Palm Springs on Capitol Hill. Riker had launched his campaign earlier this year with an eye on ousting conservative Congressmember Ken Calvert (R-Corona) from his 41st District House seat.

But should Californian voters adopt the redistricting measure Proposition 50 come this November, thus moving the Coachella Valley into the 48th Congressional District, then Riker intends to run against the incumbent, Republican Congressmember Darrell Issa (R-Vista), in next year’s contest. He is one of a number of LGBTQ candidates expected to run for Issa’s reconfigured seat.

It remains to be seen if Middleton will mount another state Senate bid when the seat is up again in 2028, as senators serve four-year terms. She “doesn’t anticipate” being a candidate next year for her city’s state Assembly seat and has not yet endorsed in the race that has drawn Jason Byors, a gay tech consultant, against Assemblymember Greg Wallis (R-Bermuda Dunes).

Wallis first won election to a two-year term representing Assembly District 47 in 2022 and was reelected last year. Both times he defeated Middleton's colleague on the Palm Springs City Council, Christy Holstege, a bisexual married mom who also cycled out of her council seat last year.

When the B.A.R. asked Middleton if she was working again or enjoying retirement post her council tenure, she quipped, “I am way too involved to retire.”

In addition to serving on the CalPERS board, Middleton also serves on the board of the Equality California Institute, the educational arm of the statewide LGBTQ civil rights organization. She also sits on the boards of the Boys and Girls Club of Palm Springs and The Campaign School at Yale University.

The nonpartisan program works to increase the number of women serving in public office across the U.S. It has been doing so for 31 years.

“It is absolutely a joy to be a part of what is truly a nonpartisan group of women that are preparing young women to seek public office,” said Middleton. “I think it is the strongest school out there in terms of preparing young women to run for political office.”

Middleton also was recently appointed to the University of Southern California’s Lambda LGBTQ+ Alumni Association Board of Directors. Among its members are Aging and HIV Institute Founder, President and CEO David “Jax” Kelly, Sysco Government Relations Manager Erick Matos, and board President-elect Kim Milliken Hayden, senior director of development operations at national education nonprofit NAF.

“I am really looking forward to working with fellow Trojans to advance the LGBTQ community within our university,” said Middleton.

UPDATED 9/17/25 to correct that Palm Springs does not have term limits for its council seats and that Middleton has yet to endorse in the state Assembly race.

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