At the height of Prohibition, the streetcar conductor manning the outbound two-car “Red Rocket” on the 26 line would pull up to the stop on the corner of Dundalk and Holabird avenues and shout:

“Racetrack!”

Racetrack was once synonymous with Dundalk’s Squire’s Cafe. It’s now a modern Italian restaurant, but in a past life was an early-20th century pool hall, speakeasy and illegal horse betting parlor.

On an unseasonably warm Saturday in January 1929, men packed into the neighborhood tavern and cast their bets to the penny on horses with names ranging in absurdity, including: Flapdoodle, Gangster, Wrench, Fasciste and a Triple Crown-contender called Virado.

The men placed wagers across races in New Orleans and Havana, Cuba, hoping their chosen steed would earn them a handsome sum.

A century later, current owner Bob Romiti commemorated the storied history of the place, now called Squire’s Italian Restaurant and Catering, by commissioning local artist Jen Egan to restore a chalk-scrawled slate board that showed the horses and odds in each race.

Egan, a Dundalk-Patapsco Neck Historical Society board member, believes the historical preservation of Baltimore is vital to teach and inspire locals and visitors alike about the area’s roots.

“It was a big thing to destroy things around here rather than preserve it,” Egan said, “so I was very happy to be a part of this.”

Filling in blackboard’s blanks

In 1992, Romiti and his brother hired a contractor to tear down an old wall in Squire’s second floor.

The man uncovered an 8-foot tall, 30-foot long blackboard hidden behind the plaster that appeared to track horse racing bets.

“Ever since we discovered it, we talked about exposing it,” Romiti said. “We didn’t know how it would turn out.”

Romiti consulted his longtime friend, Kevin Garrity, vice president of Dundalk’s historical society.

Garrity began researching the names of the horses: Who won which races? When did they take place? And, of course, how did Squire’s original owner and bookie, Fred Squires, get away with running a gambling den?

“Baltimore was pretty lax on enforcing Prohibition,” Garrity said.

The local historian did his best to fill in the blackboard’s blanks.

He discovered the entries listed are from the New Orleans Fairgrounds Racetrack and Havana’s Oriental Racetrack from Jan. 5, 1929, and Hall of Fame jockey Alfred Robertson placed second in the Oriental’s first race that Saturday with a horse named Always.

Garrity also unearthed, thanks to old newspaper articles, that local police raided Squire’s Café in 1933 and its original owner, Fred, was jailed for six months on bookmaking charges.

‘Off the wall’

Egan spent 80 hours painstakingly retracing the names of long-forgotten thoroughbreds, their jockeys’ weights and gamblers’ potential winnings.

She used mustard-colored chalk paint to highlight the horse names, which are bordered by neat, red boxes.

“They spelled a lot wrong,” Egan said with a laugh. “I mean, look at some of these names. They’re so off the wall.

“I asked Bob, ‘Do you want me to fix it?’ But he just said to keep it the way it was.”

The Romiti family purchased Squire’s Café from Fred’s widow in 1952, using a straw man.

“Apparently she didn’t like Italians very much,” Bob Romiti said.

For the past 73 years, Squire’s has been a Dundalk mainstay serving staples like “Meatball on a Heel” — three meatballs stuffed into a half loaf of Italian bread covered in tomato sauce, the first meal Garrity had there in 1965.

Story behind the board

On Monday evening, after Squire’s unveiled the restored chalkboard to the public, Garrity shared the best story he dug up while researching its past.

Back in the day, he explained, there was an underage jockey who won 13 straight races in the late 1920s through early 1930s and whose father lived in Baltimore.

Horse owners often told the jockey to hold back on horses during races.

“Surprise, surprise, a lot of those races were fixed,” Garrity said. “And one day the owner came up to him and said, ‘Let her go this time.’”

The jockey, Garrity said, immediately phoned his father in Baltimore and told him to put everything on this horse.

“The closest betting place was Squire’s,” he said. “So, his father came down and put a shitload of money on this horse and won so much that Fred Squires had to go to the bank next to pay him.”

But there’s one mystery that still plagues Garrity.

“What we don’t know is why the board was covered up and what they did after Jan. 5, 1929,” he said.

For Romiti, however, it’s enough just to have the chalkboard preserved.

“It’s there,” Squire’s owner said. “It’s history.”