The man they called the Father of Hillcrest had in fact been an undertaker. William Wesley Whittson, from Iowa, came to San Diego sometime during the late 1800s when he was 20. By 1898, he’d landed a contract that paid him to bury the city’s indigent dead. Whittson, not one to miss an opportunity parlayed that humble beginning into something larger: he became San Diego’s first coroner and in time, a city councilman.

But Whittson’s real break came during the summer of 1906 when his sister-in-law, a legal secretary at a downtown firm passed along an inside tip: the George Hill Estate was for sale, all 40 acres of it. The property lay due north of University Avenue and ran all the way back to Lewis between 2^nd and 6^th Avenues. It was the largest single lot in San Diego’s uptown region and it could be had on the cheap. The only problem was this: inexpensive or not, Whittson didn’t have the necessary coin.

Prior to Hill’s moneyed influence, the land had been little more than a weedy coyote-infested mesa riddled with impassable finger canyons that drained into the bay. There was an old Spanish mission nearby on a plot with a view that would later come to be known as Presidio Park, and Kumeyaay Indians may have hunted the surrounding bluffs but the first recorded owner of what was to become Hillcrest was a woman. Her name was Mary Kearney.

In 1870 Kearney secured a deed of trust from the city for the plot and promptly sold it to a pair of land speculators who had arrived in San Diego only a couple of years earlier. Precious little is known about Ms. Kearney, but the second owners of that land were Cyrus Arnold and Daniel Choate.

Arnold was a lawyer and a developer. Mr. Choate, on the other hand, was a man of vision who had the wherewithal to back that vision up. He’d sold his dry-goods businesses up in San Francisco when the gold rush went bust and came south. Choate now bought dirt, which was turning out to be the latest California gold rush. Over time, he would come to own much of Hillcrest, North Park, City Heights, and Mission Hills, and his partner, Mr. Arnold, would develop it. Together, they prospered.

A side note: Choate’s daughter was married to a serviceman stationed hundreds of miles away at Camp Grant in Arizona via the telegraph operator at 5^th and D, downtown San Diego, in 1876. And two years later, Arnold would found San Diego’s first real estate board, an organization that more or less survives to this day.

Whittson surmounted his cash flow problems by selling shares of his Hillcrest Company (a name perhaps inspired by George Hill?) to friends and family members, and by borrowing the balance. He set up shop at Fifth and University, subdivided lots, and saw to the building of 43 houses. But they weren’t just any houses. Spurred by a mover and shaker named George Marston (of Marston’s fame) Hillcrest was to be the new model of something being called efficient housing. Historians have noted that for the first time in San Diego building history affordable housing was targeted at small families and single occupancies.

By 1910 the streetcar had become a factor; more residents walked and used public transportation than drove, a situation that presented specific challenges to foot traffic as Hillcrest began to grow and spread out to the south, the east, and to the west. The challenges came in the form of those canyons mentioned earlier. Forested by now with the fruits of Kate Session’s labor (in exchange for the use of public land for a growing nursery, the arborist had committed to planting eucalyptus trees) they were too big to back-fill and pave over. This left but one solution: the foot bridge. Many are still in use today.

In Hillcrest/Banker’s Hill, the first of such bridges went up in 1905 at Quince Street. A wood trestle affair, it connects 3rd and 4^th Avenues. In 1912 came San Diego’s only suspension bridge at Spruce Street. It was designed by an engineer named Edwin Capps, a two-term San Diego mayor. In 1916 the Vermont Street Bridge was erected. It was a big monster of a wood trestle bridge that was knocked down and replaced with a steel facsimile in 1995. In 1931 an automobile bridge was erected on 1^st Avenue to span Maple Canyon and in 1946, the Upas Street footbridge opened.

By the 1920s, Hillcrest was a growing concern. It had become the shopping center (in the days before malls) for downtowners and surrounding neighbors in both Hillcrest and North Park. And in 1940 the Hillcrest sign at University and Fifth was fired up.

By 1940 Whittson, who had eventually gone into the lumber business in order to supply the builders of Hillcrest and Mission Hills with raw materials had again reinvented himself. This time, he built and operated the mammoth Hillcrest Bowl on Washington between Fifth and Sixth avenues. It had 16 alleys and a cocktail lounge.

The lanes would survive for years, but not so much Hillcrest itself. By the mid-40s, the little city and its residents were long in the tooth. Properties were going neglected more and more and rents, as a result, were bargain basement. This was the state of the Hillcrest community that Lou Arko found in 1963 after he moved his bar, called the Brass Rail, uptown to Fifth Avenue.

When he bought the place in 1958 the Brass Rail was not the gay landmark it is today. It was a businessman’s lunch spot with a popular happy hour. The action only turned gay with the lateness of the hour. When the building was slated to be demoed for a new high rise Arko took his piano bar north. His gay clientele, now free of the downtown vice cop hassle began to find the cheap artsy digs in the surrounding Hillcrest neighborhoods to their liking. They began to settle in. A long period of social evolution (and home improvement) began.

In contrast to Hillcrest’s growing sexual orientation a handful of wedding chapels continued on in the business of marrying heterosexual couples. One of them was the Wedding Bell Chapel, owned by the Rev. Jack and Judy Nichols, situated in a tiny white Victorian house that today is the site of the Tractor Lounge. George Tota, the Nichols’ landlord cooked in his Damascus House next door. It was one of those Hillcrest destination restaurants old as Nunu’s with a big neon sign out front in the shape of a scimitar.

Another popular night spot opened in 1960 on University Avenue (where Rich’s is today) called Mickie Finn’s. It was a cavernous club that seated over 500 and lasted for almost two decades. Lest we forget George Pernicano: he ran his huge Casa di Baffi, a restaurant that straddled Fifth and Sixth Avenues, and in his day served pizza to generations of San Diegans during the 1970s. The place shuttered and has inexplicably sat empty for the past 20-odd years.

The Hillcrest of the 1970s was also a period of quiet and nomadic hippiedom and spiritual awakening. The anchor tenant in that arena was (and is) the Self Realization Fellowship on First Avenue and to a lesser, albeit more colorful extent, the Hari Krishna on Third Avenue where they dozens of monks lived at the time in a warren of dilapidated houses. Around the neighborhood were scattered dozens of communal arrangements tucked into old rentals ranging from EST to the Arica Institute, Buddhists, past life regressioners, and just plain low-key crash pad situations.

The radio station KLRO 95 FM (“Your 50,000 watt friend of the West”) ran out of a leaky back room in a tiny free-thinking church at the corner of First and Thorn. Today the church is gone, the building having been razed in place of condos, and KLRO has become 94.9 FM (“It’s about the music.”) But in its day the little station was home to a new and growing movement that embraced health food, naturopathic remedies, yoga, tofu, juicing, Dr. Bronner’s castile soap, and something called meditation.

Kung Food, possibly San Diego’s first all-vegetarian eatery was situated right around the corner on Fifth Avenue.

Throughout the 1970s more and more gays moved to the area and rented apartments, or bought homes. Some opened shops throughout Hillcrest. The neighborhood was showing the effects of rehabbing, one house at a time. Property values escalated, commerce prospered, and tax dollars flowed -- all good news following the drubbing that Hillcrest businesses had received when Mission Valley opened and sucked away a good percentage of retail shoppers.

The gay citizenry of Hillcrest wanted to host a parade but were refused a permit. So they took to the streets and marched on downtown in 1974. The next year they got their permit. 1975 was the first of San Diego’s Pride Parades.

But sometimes, the sexual transition turned deadly. In 1991 a 17-year-old named John Wear and two of his friends, all suspected of being gay were attacked, beaten, and stabbed near 10^th and Essex after 11 p.m. by a gang of white supremacists. Wear died of his injuries; in 1992 a plaque was placed in the sidewalk nearby in memory of Hillcrest’s first hate crime.

Then, there was the isolated and odd case of Andrew Cunanan, a serial killer whose last known address was 1234 Robinson Avenue in the heart of Hillcrest.

Cunanan was born in National City, graduated from USD, and lived in San Francisco for a while before returning to Hillcrest. In 1997 he went on a cross-country killing spree that left at least five dead beginning in Minneapolis with a propane salesman named Jeffrey Wear and ending in Miami Beach with the murder of Gianni Versace.

Afterwards, Cunanan took his own life. He was 27. The motive for his murderous rampage remains a mystery but his old apartment is still listed on the walking tours of area attractions.

Today, Hillcrest is anchored by hospitals, medical centers, used clothing resellers, an Urban Outfitters store, used book stores, used record shops, bars both straight and gay, tattoo shops, coffee shops, and a growing number of restaurants ranging from the orange-and-yellow burrito triangle stand-alones to multi-cultural shops approaching high cuisine. Greek, Afghani, Japanese, French, American comfort, Chinese, Italian, Spanish, Thai, Indian: food in Hillcrest is an ever-evolving entity that continues to reinvent itself. Whatever one’s culinary tastes, it can likely be found here.

Credit for the Hillcrest foodie regime may indeed belong to the Corvette Diner, a ‘50s theme park disguised as a hamburger joint. Corvette’s was a tipping point that incited the eventual restaurant exodus to Hillcrest after the Cohn restaurant group found success decades ago in what had been an old warehouse.

No telling what the Cohens paid for the building but that same lot originally listed for $10,000 dollars way back when William Wesley Whittson subdivided the Hill Estate, put price tags on the newly-minted parcels, then sat back at his desk at 5^th and University and hoped for the best.

(In the spirit of full disclosure, Jack and Judy Nichols are the author’s parents. The author also worked at KLRO for a time.)