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Boston food critic and medium claim ghosts linger in city's historic eateries

A tour of four venues reveals spirits from mob bosses to mayors influencing staff decisions and menu preferences.

By Carolina Wood ·

Illustration for: Boston food critic and medium claim ghosts linger in city's historic eateries
Illustration generated for this article, not a news photograph.

The age of Boston's dining establishments raises a specific question for locals: are diners sharing tables with the dead? On a sunny Thursday in late October, food critic Devra First traveled through the city with psychic Tiffany Rice to investigate whether historic restaurants retain the presence of their former occupants. The pair visited four locations, each with a documented history of crime, imprisonment, or political power, to determine if spectral activity persists in modern commercial spaces.

The first stop was Fox & the Knife in South Boston. Before chef Karen Akunowicz took over the space, it operated as Triple O's, a known gathering spot for mob boss James Whitey Bulger. Rice identified a group of five male spirits in the dining room, citing the name Donald and three brothers. She linked these figures to Donald Killeen, who owned the previous establishment, the Transit Cafe, along with his brothers Kenny and Eddie and associates Billy O'Sullivan and Jack Curran. Rice reported feeling intense energy from the basement, describing it as extreme brutality, and described one spirit as a large bodyguard holding a stick who expressed no remorse for past events.

The group then moved to the Liberty Hotel on Charles Street, which formerly housed the Charles Street Jail. Inside the Clink restaurant, Rice felt that former prisoners were not treated properly and noted high levels of unsanitary conditions and smuggling. This aligns with a 1970s lawsuit where inmates claimed incarceration there constituted cruel and unusual punishment. Rice claimed to speak directly with the ghost of former mayor James Michael Curley. Curley, who served two stints in the facility, described himself as the voice of the city and stated that he helped people who lacked funding. He advised current leaders to focus on community for everyone rather than segregating it.

At the Omni Parker House, Rice immediately detected powerful energy and identified the spirit of John F. Kennedy. The former president is said to have proposed to Jackie Kennedy in the hotel's restaurant and held his bachelor party there. Rice reported that Kennedy's energy filled the dining area, rooms, and ballrooms. The spirit referenced his wife frequently and claimed the space as his territory. When asked about his favorite dish, Rice indicated he preferred home-style cooking, specifically chicken and gravy. An old menu lists roast stuffed native spring chicken with giblet gravy for $2.25, a price point that contrasts sharply with current costs.

In the North End, the pair visited Caffe Vittoria and the adjacent cigar bar Stanza dei Sigari. The building dates to 1896 and was reportedly a baby farm for unwanted children during the Victorian era. Staff member Kelsey MacKinnon described frequent unexplained occurrences, including glassware falling and employees hearing their names spoken. She showed a customer photograph featuring a shadowy figure in Victorian dress with a high white neck and headpiece. MacKinnon noted that the staff are generally open to these experiences, which they believe make themselves known.

The tour concluded at Hecate, a dark, subterranean bar in Back Bay named after the Greek goddess of the underworld. Staff burn palo santo and cinnamon and place $2 bills in an offering bowl for the goddess. Rice tuned into a female spirit with a strong personality who hummed and offered opinions on the bar's operations. The ghost criticized the new lighting and preferred the old olive garnish to the new sake-marinated lychees. Rice described the spirit as a de facto part of the staff who never physically worked there but believes she runs the place. Rice also heard messages from spirits connected to current employees, including a grandmother who passed away the previous year and a diabetic enjoying sweet treats.

The final destination was a downtown Dunkin' Donuts. Rice reported that a male spirit manager was displeased with recent recipe changes. The ghost stated that everything is too quick now and that the frosting is different from the old way. The spirit expressed a preference for the previous decorating methods.

Rice attributes the intensity of Boston's spiritual activity to the city's age. She stated that Boston is 1,000 percent more intense than other places because history continues to repeat itself. The decor may change, but the spirit remains. She concluded that spirits are everywhere, including in random coffee shops.

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