William Fleischman shows a Homlby Hills pothole.

Holmby Hills resident William Fleischman shows where a traffic cone warns of a large hole in the street surface on North Faring Road in Holmby Hills. “Holmby Hills pays millions of dollars to Los Angeles in property taxes, and we’re getting back thousands of dollars in services,” he said. (Brian van der Brug, Los Angeles Times / July 23, 2012)

When he drives his 2006 Toyota Land Cruiser to work, William Fleischman can tell if the streets he's navigating are in Los Angeles (bumpety-bumpety) or Beverly Hills (smooth). Among the worst, he says, are the roads just beyond his gated driveway in Holmby Hills, a posh L.A. enclave north of Sunset Boulevard.

Along Carolwood Drive, Faring Road and Brooklawn Drive, tree roots have buckled the concrete pavement. Cracks are visible. An orange cone alerts motorists to an 18-inch-square hole filled four inches deep with water.

Frustrated by the sad state of the streets, Fleischman earlier this month asked the Beverly Hills City Council to consider annexing the 40 or so members of the Holmby Hills Homeowners Assn. north of Sunset and east of Beverly Glen Boulevard. Fleischman said he took the step after residents hailed the idea at a May meeting and the board authorized him to look into it.

"Holmby Hills pays millions of dollars to Los Angeles in property taxes, and we're getting back thousands of dollars in services," said Fleischman, 66, a lawyer who owns a Century City investment firm.

In Los Angeles, potholes are equal-opportunity annoyers and tire-busters. The cash-strapped city said it repairs about 250,000 potholes annually in sectors poor and rich.

Whether behind the wheel or on foot, residents find the road conditions treacherous. Lauren King, president of the homeowners association, broke her foot on Brooklawn at Angelo Drive when she stepped into what she described as "a crater."

Paul Kanin, who owns the house where his son lives in Holmby Hills, recently blew the right front tire of his Audi A6 after plowing into a pothole near the intersection of Greendale Drive and North Faring Road, near Brooklawn. He waited just minutes for an auto club truck to respond to his call. The driver, Kanin said, told him: "Brooklawn is a gold mine for us. We're in the area regularly."

Some of the concrete streets still bear the 1926 Janss Investment Co. stamps. Concrete streets are much more difficult and costly to repair than asphalt-covered roads.

The city plans repairs years in advance.

"The Bureau of Street Services recognizes the need for street resurfacing in Holmby Hills and in neighborhoods across Los Angeles," said Richard Lee, a spokesman for the Los Angeles Department of Public Works. "While we sympathize with the concerns of neighbors .... the city wants to make sure it is spending taxpayer money wisely."

In the most recent fiscal year, Los Angeles earmarked $146 million, or 2% of the city budget, to repair and repave roads. Sewer projects and private construction in Holmby Hills have kept the bureau from tackling some deterioration, Lee said, but engineers aim to "address the entire portfolio of streets needing resurfacing within the next four years and the neediest streets in the next two years."

That is not soon enough for many residents.

Leaving the city of L.A., however, would be no easy matter, said Murray D. Fischer, an attorney who has consulted with Fleischman. Fischer said Holmby Hills residents might instead consider raising private funds to fix the roads.

"It's hard to imagine the city of L.A. would give up that kind of tax value," he said of Holmby Hills' proposal to join Beverly Hills.

Moreover, at least one Beverly Hills council member is not keen on the annexation idea. "I'm very opposed to it," John Mirisch said. "I understand people would like to have our services — the kinds of roads we have, the police and fire response. But extending the borders is not the solution."

Beverly Hills spends about $2.6 million yearly maintaining its streets.

Holmby Hills is the third leg of the so-called platinum triangle that includes Beverly Hills and the Bel-Air neighborhood of Los Angeles.

Subdivided in the 1920s, Holmby Hills was billed by the Janss Investment Co. as "the ultimate in real estate development," with gently rolling hills ideal for estates.

Among residents north of Sunset is real estate magnate-philanthropist Donald Bren. The late philanthropist Frederick R. Weisman's art collection is housed in a villa there. In February, the home of soap opera producer and writer Bradley Bell and his wife, Colleen, was the setting for a $35,800-a-plate fundraiser for President Obama.

("Lower Holmby," the portion south of Sunset, and home to Hugh Hefner's Playboy Mansion, is not included in the annexation proposal.)

Fleischman said he realizes that, in a city with crushing deficits, Holmby Hills residents risk seeming like "spoiled brats."

But he said he's serious about his annexation proposal, "our only option after 20 years of frustration," he said.