Speculation has raged for decades about secret underground tunnels in downtown Brentwood. They may very well be Brentwood’s best and longest kept secret.
“We’ve always heard there was a tunnel from The Torres Saloon to Rolando’s across the street,” said Contra Costa County historian and Byron resident Kathy Leighton.
Underground tunnels do in fact exist in Brentwood. They run between Sweeney’s and the Boards ‘N’ More/Moxy building, and they are also rumored to lead to other locations.
The mystery of the tunnels dates back to the Prohibition era, which was the catalyst for their existence. According to Leighton, during the prohibition from 1920 to 1932, Brentwood swarmed with speakeasies. “Brentwood had no shortage of bootleggers,” Leighton said. Many of these establishments were saloons before the prohibition and became poolrooms when prohibition started. Poolrooms were referred to as speakeasies because customers were supposed to be quiet and speak easy.
East Contra Costa County Historical Society has records of several speakeasies, including The Diablo Club, which was once known as The Torre Saloon, which is present day Sweeney’s Grill and Bar. La Costa used to be The Silver Dollar. Hairology, behind the downtown Brentwood Fire Station, used to be The City Club and was nicknamed The Bucket of Blood. Boards ‘N’ More and Moxy were once the infamous Rolando’s Saloon. The Bank of America was The Pioneer Saloon, which was notorious for bloody brawls and a brothel. The Brentwood Café was The Blue Moon.
Many of these establishments had basements, some of them interconnected with underground tunnels. There was a legitimate business on the main floor, and speakeasies were operated on upper levels or in the basement.
Sweeney’s Grill and Bar has tell-tale signs from the prohibition and underground tunnels. According to owner Peter Charitou, “Most of the tunnels have been covered with wood structures used to enforce the foundation. Most of them, not all.”
When Charitou pushed a large workstation across the room in the kitchen at Sweeney’s, a hidden trap door was revealed. After moving two planks of wood, one can descend down a rickety old ladder into the basement. “It’s where they stored the liquor,” said Charitou.
There is another basement in Sweeney’s and it is also concealed by a hidden trap door. After removing a plank of wood and taking a small plunge into darkness, one can see further evidence of the prohibition. There are remnants of a tunnel as well as stairs leading to what once was a secret entrance into the basement, which was accessible from the exterior of the building.
Across the street, Rolando’s Saloon has been split into two shops, Boards ‘N’ More and Moxy. The original stonework of Rolando’s saloon is still in Boards ‘N’ More. Moxy has the remains of a trap door concealed beneath a rug. The basement to these businesses has the remains of a tunnel, which leads across the street to Sweeney’s Grill and Bar.
Bootleggers used underground tunnels for many reasons. “The main reason is time,” said James R. Smith, California historian and author. “The more space and barriers between the entrance and the speakeasy, the more time available to clear the place during a raid.”
Underground tunnels were a great diversion for establishments with speakeasies in the basement. “It gave the ability to a patron to go to an upstanding establishment like a hotel or restaurant and visit a speakeasy without causing any tongues to wag,” says Smith.
Even with the aid of basements and underground tunnels, bootlegging wasn’t an easy job. Brentwood was notorious for bootleggers and the activity caught the attention of The Dry Squad, county sheriff employees who made raids. The Oakland Tribune reported a bust on Oct. 16, 1923 where The Dry Squad invaded Brentwood and arrested Joe Rolando and F. O’Connell, proprietors of poolrooms, on charges of possession of liquor. Both men pleaded guilty before Justice of the Peace Frank Glass and were fined $400 each.
Rolando’s luck didn’t get much better. According to Leighton, in 1925, Rolando was shot in the stomach one night while he was locking up. The gunman was rumored to be part of the black hand mafia.
This was not the first time a saloon owner was gunned down in Brentwood. The San Francisco Chronicle reported that on Dec. 13, 1915, Jimmie Torre was shot and killed in his saloon – present day Sweeney’s. At 10 p.m., Brentwood residents Jeff Barkley and Professor C.A Martin heard two shots coming from The Torres Saloon. When they entered the saloon, they found Jimmie lying in a pool of blood near an overturned table at the center of the room. A pair of glasses on a crumpled newspaper and a lit pipe lay near his mouth. The investigation revealed that the till was still filled with $190 and none of the liquor had been removed, so police eliminated robbery as a motive of robbery.
When prohibition ended, poolrooms became saloons again. Over time, history became buried in basements and walls as businesses passed hands. Many of these buildings, including the Brentwood Hotel, located at the corner of Brentwood Boulevard and Oak Street and rumored to have tunnels leading to The Pioneer Saloon across the street, have been torn down.
Some of the tunnels still exist, and shoppers walk over them without even knowing it. Like many residents of Brentwood, Charitou loves the history behind Sweeney’s and will share stories with guests. Ask him about prohibition or Jimmie Torre and the charming restaurateur will spin a tale, taking you back to a time when Brentwood was filled with bootleggers, speakeasies and underground tunnels.