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According to legend, the first jail inmate in San Diego didn’t stay for long. After all, he had a date with celebrity.

Roy Bean — later to become the famous Judge Roy Bean, a Western legend — supposedly found himself in the newly built San Diego hoosegow in 1851, when the town was a backwater in nowheresville.

Judge Roy Bean

But it didn’t take long before Bean was “observed buying drinks for the crowd at a nearby saloon,” wrote Howard W. Howard and Herbert Lockwood in their book, “San Diego’s Hysterical History.”

How did he get out? Almost 160 years later, there’s still a big disagreement on that. But one thing is clear: jailbreaks aren’t unheard of in these parts. But they aren’t always successful.

Just ask the inmate who tried to escape the El Centro jail through its air-duct system recently. He was caught and pled guilty in San Diego federal court earlier this week.

Authorities weren’t so fortunate in late 1989 and 1990, when at least 28 inmates escaped from the county jail in Chula Vista in several jailbreaks. A whopping 13 prisoners escaped at once in what is apparently the largest jailbreak in county history.

During that escape, the inmates got out by sawing through steel bars with hacksaws that they’d been slipped from someone on a public passageway above the underground jail.

Several of the inmates were later apprehended.

More recently, an inmate escaped from Otay Mesa’s Donovan State Prison in 2008 but was later captured. Electrified fences keep high-risk inmates inside the prison, but the escaped prisoner wasn’t one of them and apparently only had to scale a six-foot fence.

Roy Bean had better luck back in 1851.

One story says he was arrested on a misdemeanor charge and got out of the Old Town prison by using a jackknife to cut through soft mortar. But author Brian McGinty contends the story is a bit exaggerated in his book “Strong Wine: The Life and Legend of Agoston Haraszthy,” a biography of the early San Diego sheriff and famous vintner.

In reality, it seems, Bean — later known “The Law West of the Pecos” (and the future subject of a Paul Newman movie) — got in trouble by wounding a Frenchman in a duel.

Bean landed in jail, but his “señoritas” were distraught and brought him gifts. As one contemporary writer put it, “concealed among the fragrant petals of the bouquets, or maybe imbedded in the succulent hearts of tamales, were tools of escape.”

But there’s another take, too. A newspaper account said Bean shot a Scotsman, not a Frenchman, and waltzed out of the jail because it had no guards.

Bean went on to a famous career as a colorful Texas judge who, according to Wikipedia, chose jurors from among his best saloon customers and expected them to buy drinks during breaks. He also fell deeply in love with a beautiful British actress by the fantastic name of Lillie Langtry, even though he never met the lady.

Back in mid-19th century San Diego, the jail remained less than an impenetrable lockbox, at least when a friendly sheriff was around.

The city attorney, G.A. Benzen, complained to a friend that robbers, murderers and other miscreants were treated like kings.

The sheriff, he wrote, would accompany inmates to a hotel where they would “jointly take their eye-openers, bitters or nightcaps as the case may be.”

No word on whether they got mints on their pillow too.

— RANDY DOTINGA

Randy Dotinga

Randy Dotinga is a freelance contributor to Voice of San Diego. Please contact him directly at randydotinga@gmail.com...

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