This last June 15 was something of a special milestone for Palm Springs Mayor Lisa Middleton. Middleton is only the third openly transgender mayor of an American city and the first in California. On that day, she was celebrating her 70th birthday. What made it exceptional was that she wasn’t celebrating it with her wife, Cheryl, and kids back in Tahquitz River Estates. She was celebrating it in the West Wing of the White House as an invited guest of President Joe Biden and his wife, Dr. Jill Biden, to commemorate national Gay Pride Month. 

It was an emotional moment, one that brought home sharply the long road she’d walked since leaving her childhood home in Bell Gardens.

“The journey of coming out as transgender is a really tough one,” she says in her characteristically soft voice. Precise and articulate, the tenor of her voice has the effect of making her listeners pay close attention. “Making changes in how you present yourself doesn’t happen overnight. It requires a tremendous amount of honesty with yourself as to who you are. I don’t care who you are; you will have doubts as to whether you can pull it off. I certainly had doubts. To get up nearly 30 years after coming out and find that I was going to be walking in the West Wing of the White House on my birthday was as humbling and gratifying as I can possibly imagine.”

Both sets of Middleton’s grandparents were refugees in the Great Dust Bowl migration. They arrived in California with nothing. When her grandfather lost most of his arm in a factory accident, the compensation he received allowed him to buy a small home near Bakersfield, thus becoming the first homeowner in the family (It was also an incident that left a deep impression on 11-year-old Lisa, leading her ten years later to a 37-year career with the California State Compensation Insurance Fund). Middleton grew up poor in Bell Gardens (aka, Billy Goat Acres) where many Dust Bowl migrants congregated because of the cheap housing and proximity to war-era production plants. Middleton remembers occasional family road trips out to Palm Springs where her father always stopped in Cabazon so his kids could play around the dinosaurs because “it was free and he was cheap,” she laughs.

Her family didn’t have the means to send her to college (and Middleton isn’t sure she had the grades at the time to be considered), but she credits the two years she spent at East Los Angeles Community College with changing her life. It allowed her to complete her undergraduate education at UCLA and then pursue a master’s degree in public administration at USC. She had already joined the State Fund department after completing her BA, but she returned to UCLA several years later for a post-graduate certificate program with the LGBT Leadership Institute. Though it was over twenty years ago, Middleton says it’s important to remember that the LGBTQ world was different. “One of the questions that we were asking ourselves constantly during that week was: I’m out, but what does it mean to be out within a larger organization? How do we take and express ourselves and our community in a meaningful way within the corporate structure?”

These were questions that Middleton had to ask and answer herself several years before as she readied herself to come out in 1995. “I didn’t just wake up one morning and announce (myself). I knew a few people through a transgender legal organization who had successfully come out in corporate life. I received incredibly good help from (State Fund’s) employee assistance program (and) I was working in San Francisco at the time, and certainly San Francisco has always been on the leading edge of acceptance and openness. While my coming out was somewhat different than others, there was a tradition within the city of acceptance, and we were able to build on that.”

Middleton says it was an incredibly demanding period of her life, but she is proud of the way she handled herself and the support she received from colleagues. Nevertheless, there were obstacles and some colleagues who were slower in their acceptance. “There was one fellow who…was really struggling. We couldn’t find conversation. A few months go by and we end up on an elevator together alone and something clicked in my head. This guy played golf all the time. I asked him, ‘How’s your golf game?’ That turned out to be the right question to break the ice. What I think is important about this story is that all of us have that right question that opens the door. And, usually, it’s a very simple question.”

After retiring in 2010, Middleton and her family owned “a gorgeous house” in north San Diego County. However, it wasn’t long before the long commutes to the appropriate health providers in San Diego and the lack of community connection in their affluent suburb began to take its toll. Middleton and her wife had been coming to Palm Springs for their anniversaries since they were married and visited even more frequently once they were living in San Diego. In 2011, they made an offer on a house in Tahquitz River Estates and made the move.

Middleton did not make any conscious or concerted effort to involve herself in city politics.. At first, she says it was simply a way to make connections in their new community. She recalls that before attending her first neighborhood organization meeting, she made sure she read the organization’s bylaws. At the meeting, the neighborhood council was up in arms about what to do about a controversial member who was constantly making trouble. Middleton raised her hand, stood up, indicated her copy of the organization’s bylaws, and pointed out the fallacy of the issue by quoting the appropriate passage. “I guess it was a dumb thing to do,” she admits ruefully, “because they elected me president within an hour.”

From there, she became involved in the Organized Neighborhoods of Palm Springs, was appointed to the planning commission and, in 2017, she was elected to the Palm Springs City Council. In 2018, when the city went to districts, the city council adopted a system where the office of mayor would rotate among council members. Middleton explains that our normal idea of a mayor is the chief executive of a city like Los Angeles or Chicago. In those elected positions, the mayor is not a member of the city council. The mayor is, like the president of the United States, a distinct branch of government. However, in a city like Palm Springs, the city manager is the position responsible for budgets, hiring and firing of executive positions, and carrying out executive tasks. “In the city council system, the mayor leads the council but is only one vote on the council. You’re running the city council meetings and hoping to get two other council members to agree with you on issues.”

Middleton says the problem with having a separately elected mayor in a city the size of Palm Springs is that it can often give the public an exaggerated sense of the mayor’s power and, conversely (if one thinks back to 2015), it can also give the mayor an exaggerated sense of their own power. 

One of the issues on which Mayor Middleton has been particularly outspoken is the College of the Desert’s failure to make good on their promise to build a campus in Palm Springs. Originally, the city purchased 119 acres north of the city from the federal government for $2.1 million and then gifted the land to COD in exchange for building a campus on the site. Instead, COD bought the old mall on East Tahquitz for $22 million, though its plans for a Palm Springs campus have been downsized considerably. COD is attempting to sell the 119-acre parcel to a developer. The city has offered to buy the property back from COD (for the same price the developer is offering) and has cried foul in regard to COD’s intended sale. Middleton’s issue with COD is not so much the way they’ve done business, but at the opportunities that are being denied students in the west valley and North Palm Springs/Desert Hot Springs. “As I’ve said on many occasions, I wouldn’t be here today if it wasn’t for community college. Like most of the students at COD, I was the first in my family to attend college. It matters that there is a college close by for students.”

Furthermore, she says “there is a perception on a broad part of the populace that the western part of the Coachella Valley is not being treated fairly when it comes to a campus that was promised. We had the potential on the COD (Palm Springs) campus to work with Cal Poly Pomona on a Palm Springs architecture school. That’s ground-breaking to be able to align with a Cal State campus. Every city in the valley has reason to be proud of who they are, but no city in the valley has the worldwide brand of Palm Springs when it comes to architecture and design. I’m hopeful we can put this back together because I think it’s really important.”

Despite feeling awed by her invitation to the West Wing, the mayor doesn’t feel a particular historical weight on her shoulders being the first transgender mayor of a California city. To her, the success and world-renown of Palm Springs is something shared by the town’s entire gay community. “If you go back to the 1980s and 1990s, there was plywood across the downtown areas. Our restaurants were not booming. Cities such as La Quinta and Rancho Mirage were being created. The retail moved to El Paseo. I remember a story from the LA Times during that era. A gay man (was being interviewed) and his comment was ‘These people don’t know what they have,’ referring to the mid-century homes, the Alexanders and the Wexlers. It was largely the gay community who moved into those homes, fixed them up, started businesses, and created the dynamic of investing in downtown. Our residences became a place where people wanted to live…and then the business community expanded rapidly in response. Twenty years ago, the city revenue for Palm Springs was just under $40 million. This year, it will be in excess of $180 million. That growth took place (when) an LGBT council was the majority. I think we’ve been good for values in this city. I know we’ve been good for business.”

The mayor says that her wife, Cheryl, often jokes that she wishes Middleton would get a real job so that once in a while she’d take a day off. Cheryl should be careful what she wishes for. Middleton, with the strong support from Democratic colleagues in the state legislature, has decided to enter the 2024 race for the 28th Senate district, a traditionally Republican seat currently held by Melissa Melendez of Lake Elsinore. She knows it will be a tough race and that she’ll be very busy for a few years to come. Nonetheless, she admits that having found her voice while campaigning for city council, she now really enjoys using it. 

And she feels particular inspiration from a small but momentous exchange during her first campaign. “We were doing a fundraiser at a friend’s house in the San Diego area. There was a reception line at the fundraiser and a little girl about five years old walked up to me and put her hand out and said, ’Hello, I’m Lori. I’m like you. I’m transgender,’” Middleton says, her eyes growing glassy.  “As the reception was winding down, she and I found a table and just sat and talked. It was probably only fifteen minutes, but it felt like forever. It was just unbelievably gratifying to be present for Lori.”