Getting Rich

It’s 1 p.m. on a Wednesday and about 100 mostly middle-aged people attired in tracksuits, fleece pullovers, and Hawaiian shirts are filing into rows of chairs in Horseshoe Casino Baltimore’s multi-story entertainment venue, 14Forty. Lights are low, and spotlights swivel across a stage with three podiums. Outside the venue, gamblers sit at the casino’s 275 gaming tables and 2,200 video slot machines, which feature names like “Miss Red,” and “Lobstermania 2.” The machines clang and whir while the soft-rock strains of Phil Collins emanate from the loudspeakers. Aside from that though, the space is fairly empty and sedate. But that’s all going to change. People Are Winning, the casino’s new live game show, is about to start.

A booming voice reminds everyone to take a seat. Light shines on a blonde woman in a form-fitting black dress, who quickly explains the rules and the potential spoils. The big prize is hundreds of dollars in rewards points, code for money you can use to play at the casino. Then, it’s show time.

“Let me please welcome Mr. Richard Sher!” shouts the blonde.

The theme from the 1978 Superman movie plays, and people cheer as a white-haired man in a charcoal suit and a bright red tie emerges from the shadows, a microphone affixed to his lapel. “Hello, everybody!” he calls.

Though everyone present seems familiar with the genial septuagenarian, Sher wastes no time reminding the assembled of his local media credentials.

“Welcome to People Are Winning, sort of like People Are Talking, except I’m paid a little better,” he jokes, referring to the local morning talk show he co-hosted on WJZ-TV during the late ’70s and early ’80s with a certain future media mogul as his co-host.

“Oprah’s a multi-billionaire, and I’m with you. She’s eating caviar; I had a Kosher hotdog,” Sher continues with a chuckle. Yes, he means that Oprah, who earned her stripes on Baltimore’s airwaves before moving onto Chicago and subsequent world domination.

Despite the self-deprecating comparisons, Sher doesn’t seem bitter. In fact, he seems downright delighted. Like most natural-born performers, he isn’t concerned with the size or demographics of an audience, just that there is one.

A cymbal clangs, and there’s more laughter. Two women stand up from their seats to shake Sher’s hand, and he obliges. Then, with a gleeful grin, he asks the crowd, “Are you ready to play?”

Game-show host is just the latest professional incarnation for Sher, whose career has spanned five decades and encompassed radio and TV, reporting and anchoring, hard news and fluff—and now, master of ceremonies at Horseshoe.

At the beginning of 2015, Sher’s friend, Sandy Hillman, whose communications firm handles public relations for Horseshoe Baltimore, asked him to breakfast. The casino’s staff had been discussing ways to expand the entertainment offerings and bolster midweek attendance, and a light bulb went off in Hillman’s head.

“I said, ‘Richard, how’d you like to do a game show?’” Hillman recalls. “He was the perfect person. . . . he has a humorous, off-beat personality, he’s warm and engaging, and he’s comfortable on stage.”

“He likes to meet people, to be around people, and I think that’s what he missed most.”

Sher was open to the idea and, together with marketing firm The Breakthrough Group and Horseshoe, hammered out the format. Three contestants are chosen at random, but audience members can win, as well. Question categories include Baltimore trivia with an emphasis on the nostalgic. They selected Caroline Arbaugh, a panelist on Square Off, the public-affairs program Sher hosts on WMAR-TV, to be his assistant.

Calling from Los Angeles, Winfrey believes her former co-host has a natural knack for hosting a game show. He never fails to make her laugh—even one time when he visited her in the middle of the night in the hospital.

“He’s always been one of the funniest people I’ve ever known. Even in my younger days, one of the hardest things was not to laugh out loud on the show,” she says.

People Are Winning debuted on April 8, and Sher calls it “a trip.”

“This is great fun,” he says. “I’ve always been a community person and a people person, so it gives me an opportunity to interact with people, which I used to do every day.”

Plus, he gets to wear the bright ties he loves, something he doesn’t do as much of on the more straight-laced Square Off.

“Here, I just get to be me. I am who I am.”

Sher was born at the former Women’s Hospital in Bolton Hill, and grew up in Northwest Baltimore.

Sher’s parents met when his father, Michael, was working as a salesman at the Park Circle Motor Company, a successful car dealership owned by the prominent Legum family. Sher’s mother, Lillian, was the boss’ daughter and ran off with Sher’s father, a minor family scandal that Sher still recounts with relish all these decades later. Together, Michael and Lillian settled along Gwynns Falls Parkway and had first a daughter, Linda, and then Richard.

Even in his early days, Sher had a flare for performance. He played emcee at dances at St. Paul’s School for Boys—where he says he was one of the few Jews. His formative years are even immortalized on film—Sher was one of the original “diner guys,” portrayed in Barry Levinson’s 1982 film Diner. In fact, he and Levinson were roommates for a period during college while Sher was at University of Maryland and Levinson attended American University. Later, Levinson cast Sher in a cameo role in 2006’s Man of the Year starring Robin Williams.

According to longtime friend and WJZ-TV reporter Ron Matz, Sher has always had the same colorful personality.

“He’s as crazy as he was the first day I met him,” says Matz, who got to know Sher during his early reporting days. “Actually, I think he might be crazier now.”

In college, Sher got a job at the school’s radio station and found he liked it. He worked at country, rock, and news stations, in Washington, D.C., and later San Francisco, before returning to Baltimore. In Charm City, Sher, a self-described news hound, made the switch to TV, landing at WJZ in 1975 as a general assignment reporter and, eventually, an anchor. His wife, Annabelle, who he met in college, and their three sons were along for the ride.

It was during this time that Sher racked up many of his most-cherished war stories. Along with co-hosting with Winfrey from 1978 to 1983—they are still close friends and talked every day during this spring’s Freddie Gray riots and protests—he has been on the frontlines of some intense and dangerous new stories, sometimes even becoming part of the story himself. He witnessed Maryland’s first lethal-injection execution, talked a guy off the roof of the University of Maryland Medical Center, and got involved with a hostage situation, where he convinced the perpetrator to release the farmer held at gunpoint.

“I don’t miss the murders. I didn’t miss the riots. I’m really happy with what I do,” says Sher.

“I would [cover] a murder a day,” Sher says. “The names were different but the sound bites were always the same. Children’s murders, children’s funerals, hit-and-runs.”

Yet, he valued the pace of the job, and how each day was different. He knew he was informing and entertaining the public, though he wasn’t exactly waging a battle against public corruption or exposing national secrets. Instead, he got satisfaction out of being the only reporter to interview a murder victim’s family, the one whose name opened doors.

“I had the easiest job,” Sher says. “You’d go in in the morning, you’d go out and do a story. . . . you put it on the air, you go home. You don’t have any baggage to take home.” And, “everybody knows you.”

But it still ground him down and, eventually, he’d had enough. Still, he found it difficult to step away from the job he loved and the image he’d been associated with for 30 years. Sher first tried in 2004, then 2006. Each time, he couldn’t go through with it. Even on his last day in 2008, he says he asked his boss, “Can I still change my mind?”

“It was very difficult for him,” Annabelle Sher says. “I think it was because there was no transition; the end of his career was very abrupt. He likes to meet people, to be around people, and I think that’s what he missed most when he left.”

Sher describes his mood during that time as “unhappy and really down.”

“I was upset about it. It took its toll on me emotionally,” he says. “But eventually, I came out of it.”

He began volunteering at the R Adams Cowley Shock Trauma Center—now, he never leaves the house without his Shock Trauma wristband. Then, nearly six years ago, he resurrected the feisty Square Off—which he’d hosted for 19 years on WJZ-TV—on Baltimore’s ABC affiliate. And, of course, now there’s People Are Winning.

Noah Hirsch, the vice president of marketing for Horseshoe Baltimore says that, so far, the game show has done exactly what it’s supposed to do—attract more weekday traffic. Each week, the audience has grown, approaching as many as 200 people.

Sher is pleased, too. “I’m as busy as I want to be,” he says, “and I don’t miss the murders. I didn’t miss the riots. I’m really happy with what I do.”

Back in the casino, under the lights and adoring gazes of the public, Arbaugh, the blonde in the black dress, chooses three pieces of paper from a suitcase and reads the name of the first contestant aloud.

“Dona Fontaine.”

A woman in an orange blouse and straw hat stands up, her face registering her surprise. Sher walks over to her and shakes her hand.

“Dona, how are you? It’s been a long time,” he says, immediately shifting into flirting mode. “I think I left my coat at your house.”

The crowd laughs and Fontaine keeps hold of his hand a little longer than maybe she should. She doesn’t tell Sher, but she has seen him in person before—at a taping of People Are Talking in the 1980s. And, she thinks to herself, the only thing different about him is that his hair is whiter now.

Arbaugh announces two other women’s names, and both are ecstatic. Sher helps all three ladies shed their coats and put their purses on a nearby table before they ascend a staircase to the platform.

Each contestant stands behind a podium, and the questions begin. Categories include “Sports” and “Current Events,” but today, “We Are What We Eat” is the most popular. If the contestants don’t know an answer, a member of the audience tries. Each correct response is awarded with another receipt-like paper, good toward $20 of gambling or a discount at one of the casino’s restaurants.

As Sher poses questions like, “Name one of the Orioles’ TV announcers,” and “What grocery store chains existed before Giant?”, the crowd begins to grow. Horseshoe employees in their ruffled, gold blouses stop by, clapping wildly when Sher shills for his employer, saying, “Have you ever seen a more beautiful casino than Horseshoe? Absolutely fabulous.”

Sher is in his element, a ringmaster of sorts. “Quiet, will ya?” he shouts when someone tries to call out an answer. He jokes that he and a male show assistant are getting married that weekend because of “a new law in Maryland.” And when he asks one of the contestants if she sings and she launches into, “You Are My Sunshine,” he gets everyone to join in.

The crowd eats it up. As Sher quips about whether a contestant is a natural blonde, a woman in the audience turns to her husband and says, “This is fun, isn’t it?”