Miss Billy Riley




Meet the delightful, unflappable managing director of the Horton Grand Hotel


The speaker took a deep breath before beginning the introduction of Miss Billy. “She was the first woman director of the San Diego Chamber of Commerce in 63 years, the first woman director of the San Diego Convention & Visitors Bureau, the first woman general manager of a major San Diego hotel and the first woman president of the San Diego Hotel-Motel Association.

“She served as president of the greater Shelter Island Association and of Old Town’s Chamber of Commerce, in addition to serving on the board of directors for the Gaslamp Quarter Council, Cystic Fibrosis and the Crime Victim’s Fund,” the speaker continued. But she was not yet finished.

“She was named ‘Woman of the Year’ by the Soroptimists of San Diego and was selected by San Diego Women in Travel as ‘Travel Person of the Year,’” she concluded as Miss Billy made her way to the podium precisionly timed to arrive as the speaker said, “I am proud to introduce San Diego’s Miss Billy Riley.”

“You know,” the silver-haired, blue-eyed Southern charmer slowly began with the hint of a drawl, “I keep saying my introduction is beginning to sound more and more like a memorial service.” With that she gave the audience a peek at her priceless sense of humor.

The 71-year-old managing director of the Gaslamp District’s historic Horton Grand Hotel is still collecting awards, is still sought out to serve on numerous boards and shows no indication nor inclination of slowing down. Her contract with the hotel, she exclaims with pride, goes to the year 2001, and considering her genetic background, it’s very likely she will fulfill that contract.

“I had one great-grandmother live to the age of 101 and another lived to be 106,” Riley says. “Just before her death, that great-grandmother appeared on an Oklahoma City television program. When she was asked if she had one more wish what it would be, she responded that she thought she might like to get married again.”

Miss Billy, as she is affectionately called, can be seen sashaying through the glass atrium lobby of the Horton Grand, complementing the surrounding Victorian environment in one of her antique period dresses. Carrying a white lace parasol, she continually stops to chat with guests and to parade her attire, playfully twirling around the parasol.

“Good morning, ladies. Please come in and look around. We love to have you here,” she greets newcomers with a smile. That same smile has been described as so contagious it has caused many a guest intending to complain to forget his complaint. And using her Southern accent to its greatest advantage, she just as gently guides her staff, also dressed in period costumes.

Riley’s entry into the business world was not particularly conventional—it was driven by necessity. Soon after arriving in San Diego from Dallas in 1944 with a child and a husband in the Army Air Forces, she divorced. Because her small son had an asthmatic condition and her parents lived in San Diego, she stayed. She received no child support and quickly came to a realization: She had to go to work.

However, Riley didn’t just get a job. “I remember never having fewer than three or four jobs at a time,” she recounts. During one period, she worked for an accounting firm during the day, an advertising agency after 5 p.m. and at 10 p.m. went to an upper Fifth Avenue nightclub where she sang the blues till the wee hours. And on Sundays she took inventory for a furniture company.

“I call myself Miss Billy Riley, my maiden name, because of my days as a singer,” she says. “There was some question as to whether I had any talent but people said I sure had a lot of audacity!”

From 1949 to 1961, she was the receptionist for a doctor who was also an investor in San Diego’s first resort property, the Half Moon Inn on Shelter Island. The property was struggling. Tourism hadn’t yet come to San Diego—it was still just a Navy town.

Riley was hired to handle the resort’s public relations. As the San Diego Union said, “. . . The owners bet on a long shot. They sent in a doctor’s receptionist, a woman with a man’s first name, to do some promotion . . . Billy Riley put on its feet a nine-year-old resort hotel that had arrived before its time.”

“Those were desperate, desperate times,” she says. “Occupancy was low—5%. So I had all the hotel employees park their cars in the spaces reserved for guests and I turned on every light in the place at night. That brought in the first tourists. I knew times were changing when I could quit sewing together twin sheets if we needed a king-sized bed that night.”

Riley’s ingenuity was recognized and she eventually became assistant manager and soon manager and vice president. Her entertainment background surfaced and she began “staging” her first hotel.

The Polynesian paradise

The Half Moon Inn was transformed into a Polynesian paradise and Billy was as comfortable in her muumuu as she is today in a lace period dress. Even the trams that transported guests had “the look” with their thatched grass roofs. Guests described the property as being “more like the islands than the islands.”

The reputation spread and the resort soon became a haunt for celebrities. Nan and Frankie Lane lived there 13 years and regulars included Desi Arnaz, Xavier Cugat and Lana Turner. And because of its romantic charm, many newlyweds honeymooned at the Half Moon Inn, including President Johnson’s daughter, Lynda Bird, and her husband Charles Robb.

In 1969, Sheraton bought the thriving Half Moon Inn and Riley went to Los Angeles as a vice president for Amfac hotels, staying only one year. “I have to tell you,” Riley says, “I was not a Los Angeles girl. In that city, I was lost more than I was found.”

Riley was flying to Chicago to resign when her plane was forced down in Cleveland because of snow. As fate would have it, a former investor of the Half Moon Inn, Irving Kahn, was in the airport. After a short visit, he hired her to manage his Murrieta Hot Springs’ hotel-condo resort.

Under Riley’s tutelage, one of California’s old watering places became a renowned spa, catering to celebrities and the privileged. Frequent visitors included Barbara Marx (Sinatra) and the Gabor sisters. Riley stayed on the job until Kahn’s death in 1973.

“Time for romance? Oh, yes,” she says, remembering a particular captain in the Navy. “But I thought deep down he was just a playboy and would never amount to anything. So he went back to Washington and became an aide to President Kennedy—a member of the inner circle.” She laughs at her “intuition.”

Riley “retired” and she and her mother moved back home to Erick, Oklahoma, so her mother could be with her family. “I’ve always been intrigued with real estate—just making something out of nothing—and at that time I was used to the California prices of $120,000 or even $180,000. In Erick everything was $1,500, $2,000 or maybe as high as $3,000. So I just went down the street saying, ‘I’ll take that and that and give me more of that.’ I wound up with a restaurant, an antique shop, a wood shop and a gift shop. Now bear in mind that I would have to go in the kitchen of my restaurant, cook the meal and then run out and sit on the stool and order because I probably wasn’t going to have another customer the rest of the day,” she cheerfully recalls.

When Riley was arranging to have her utilities turned on, the rep asked her occupation. She paused, then said, “Well, I’m no longer a hotel manager.” After another pause and some thinking about her current property holdings, she added, “Well, I guess I’m sort of an investor.” The rep turned back to her typewriter and typed “Unemployed.”

Having never thought of herself as “unemployed,” Riley thought, “What am I doing here?” She and her mother returned to San Diego. And in Erick, she still owns what she refers to as “some of the most non-negotiable real estate in the country.”

The beckoning

Determined to stay out of the hotel business, Riley opened a store to sell all her “junk” (as she referred to it). The shop was appropriately named “Billy Riley’s Gaslamp Emporium—Experienced Merchandise.” It was there that she met Dan Pearson, developer of the Horton Grand Hotel, the ambitious resurrection and restoration of two of the city’s oldest hotels into the Victorian classic it is today.

After he saw old scrapbooks from Riley’s Half Moon Inn days—the resort’s transformation and its appeal to celebrities—Pearson repeatedly asked Riley to manage the Gaslamp property.

Countless “no’s” later and eight years ago, Riley finally agreed to go with Dan, first as an investor and then more ambitiously as the manager, the director and the interior decorator of the Horton Grand Hotel. Over the past year she has also been working on Phase 2 of the project—the Chinese Regal Suite Hotel—due to open on July 1.

Admitting that there are not enough hours in the day before the summer opening, Riley isn’t seen as often strolling through the lobby in a long silk Victorian dress. In fact, it’s more likely that she’s in the basement of the Chinese Regal in casual pants and tennis shoes, rolling up her sleeves right along with the others and doing whatever it takes to get the job done.

Most recently, the tourism industry recognized Riley with the industry’s highest honor—the R.C.A. Lubach Award. When the award was announced at the annual meeting of the San Diego Convention & Visitors Bureau, the 550 attendees gave her a standing ovation.

Typical of Riley, her interpretation of the event is that she was unsuspectingly eating her salad when her name was announced and “Honey,” she recalls, “I almost choked. I was just shocked but once I gained my composure, I was truly thrilled with the honor.” In spite of her many awards, Miss Billy Riley continues to take the greatest pride in her son Mike Wofford, of whom she says simply, “He’s a brilliant, brilliant boy.” Then she softly laughs at her reference to Mike. When her “boy” once made a comment regarding his age, her surprised response was, “Are you 46? My gosh, you’re older than your mother.”

But like his mother, Wofford has significant accomplishments to his credit. He is a world-famous jazz pianist who has traveled with Sarah Vaughan and Ella Fitzgerald and he’s played Carnegie Hall. He and his wife, Gina, have made Riley the grandmother of six with one great-grandchild.

“Now that I’m older . . . I mean, now that I’m old,” she says, making the word “old” sound like a three-syllable word, “I know that if I’ve had any success in life, it wasn’t because I was smarter; it was because I was there earlier, left later and worked harder.” Miss Billy Riley—a woman of vision and a woman of firsts—was truly a “San Diego Woman” long before it was fashionable.

Copyright 2018 Cynthia Dial. All rights reserved