Two friends: One’s been to prison, the other’s going

LAS VEGAS — The two men are best friends, a burly odd couple pounding down meaty sandwiches at a steakhouse here. The mood was heavy. One will soon take a long trip to a place the other has been before, where the beds are hard and so is the time.

In a few weeks, former Hells Angel Charles “Pee-wee” Goldsmith, 57, will enter the state prison system for a stretch of two to five years — convicted on a host of charges following a 2008 brawl at a downtown wedding chapel between rival motorcycle gangs.

Frankie Citro, 69, has also seen the wrong side of the law. In the 1980s, the onetime blood-and-knuckles mob enforcer did two years in a federal prison for loan sharking and became a quick study on how to stay invisible behind bars.

The old ex-con was offering hard-earned wisdom to his friend, whom he met outside prison walls through a shared love of doo-wop music. “You’re probably the only guy I know who knows more about doo-wop than I do,” he said. “That’s amazing.”

The long goodbye continued Saturday night when Citro threw a dinner at the Italian American Club for Pee-wee and his son Brad, 33, also sentenced in the fight.

Even for Vegas, a city known for the unscripted, the event stood out: a fundraiser by one tough guy for another tough guy of a different stripe.

Citro had circulated an event flier using his own brand of streetwise humor. “Our pal, Pee-wee, and his son Brad will be leaving soon on a ‘Government Sponsored Vacation.’ With your help, they will be able to keep their lives in order at home.” Any donations, he said, “will make sure Pee-wee and Brad know who their friends are.”

Citro is a former boxer who’s still sturdy as a fire hydrant. As emcee, he cruised the ballroom in a tuxedo, microphone in hand, extolling the guest of honor, whose nickname is a cartoonish misnomer.

Pee-wee (everyone calls Goldsmith that, so we will too) stands 6 foot 8 and weighs 400 pounds. He wears size 16 shoes and his hands are ham hocks. His body is covered with tattoos of skulls and cherubs. A loner who has made a living off his mammoth body, he’s a bouncer, brawler and bodyguard who calls people “bro.”

Dressed in black, a gold necklace hanging from his neck, Pee-wee towered over a crowd of 150 people that mixed tough guys in fedoras, strong cologne and tailored suits with bikers in skullcaps, bandannas and wallet chains — one taking to the dance floor with a large knife handle sticking ominously from his back pocket. Table signs directed guests. One read “Frankie,” the other “Pee-wee.”

Local bands including the Nite Kings, Goodfellas, Touch of Silk and Richie D & the Hi-Lites donated their time to croon hits by Lou Rawls, Elvis and the Spinners, each offering encouragement to the big man who sat up front. “Time’ll go fast,” one performer said. “Don’t worry about nothin’.”

Robert Nash, a comic who impersonates actor Robert De Niro, had more advice: “Pee-wee, when you get to the hotel, get a room with a view. And don’t take no grief from nobody.”

For Citro, that part was no laughing matter. Days before the party, as he sat with Pee-wee at the steakhouse, he shook his head. The big man’s menacing presence, he knows, could bring him trouble in the big house: unwanted confrontations with inmates that will only extend his sentence.

“He’s a proud man; he walks with his head tall, but his size will bring him trouble,” he said of Pee-wee. “Inmates will challenge him to climb the ladder, like gunslingers going after Wyatt Earp.” He leveled his gaze at Pee-wee. “Look deep into yourself. Don’t respond. It will only put you further away from your goal: Do your time. Come home.”

Pee-wee stared back silently. For decades, he’s lived by a don’t-mess-with-me code that’s become an enduring life’s truth. When someone got in his face, he’s always responded. How do you suddenly just switch that instinct off?

He grew up in Milwaukee, a product of the streets. His father was also big, a carnival wrestler; people paid to survive a round in the ring with him. Pee-wee quickly excelled in sports like wrestling and football. He also fell in love with motorcycles.

He got the nickname after he joined a local club. That was about the time actor Paul Reubens, known for his character Pee-wee Herman, was arrested for lewd conduct in a movie theater. He was horrified. The bikers laughed. The name stuck.

The scrap that sent him to prison took place on Brad’s wedding day. Rival bikers showed up at the chapel. There was a confrontation, and prosecutors said Pee-wee started a rumble that left one man stabbed. Brad blames his father for what happened; the two barely remain on speaking terms.

Stress has been building as Pee-wee prepares to walk into the system March 18. His wife is a mess, his daughter traumatized. On a trip back to Milwaukee to see his mother, he ran into an old biker buddy who once did 25 years in prison. While he was away, Pee-wee sent money and watched over his friend’s mom. He recently told his pal, “Don’t forget me like I never forgot you.”

He needs no such words with Citro, who advises him on the ways prison officials might try to break him, such as sticking him in undersized clothing “so he walks around like Charlie Chaplin.”

Pee-wee has been in jail; never prison. A construction job mishap years ago left him trapped underground, making him wary of closed spaces. Like small cells. Or solitary confinement.

When Citro talks, Goldsmith listens — especially now: “I’ve never had a guy look after me my entire life.”

The old man looked over the table: “You’re a man; you’ll take what’s coming.”

At the party, the two had a last laugh. Citro created a prop: a large white door with black bars and a sign reading “Jail.” The odd couple posed for pictures before a scene that symbolized a hard place one already knows well, and the other soon will.

john.glionna@latimes.com