There is a mansion in Farmington, Connecticut, that has bankrupted almost everyone who has owned it. Built on fraud, lived in by a boxing legend and a rap superstar, and sold at a loss again and again, the 52,000-square-foot estate at 50 Poplar Hill Drive is back on the market — this time for $9.9 million.
Built on the Biggest Fraud in Connecticut History
The story starts in the mid-1980s with Benjamin Sisti, founder of Colonial Realty, one of America’s largest real estate syndication firms, controlling roughly $2 billion in property across 80 partnerships. In 1985, Sisti completed a 52,000-square-foot mansion on more than 17 acres near Hartford, spending a reported $2.3 million on construction. It had a private lake, a tennis court, a four-bedroom guest house — and, by most counts, around 20 bedrooms and 40 bathrooms.
Behind the facade, Colonial was a Ponzi-like fraud: investor money taken in as finances collapsed, millions funnelled to relatives, even public officials bribed to keep pension money flowing. An estimated 7,000 victims came forward, some claiming to have lost life savings. It still stands as the largest real estate fraud in Connecticut history.
In 1990, Sisti and Colonial declared bankruptcy — Sisti claimed just $15,000 in cash. The mansion slipped into foreclosure, was acquired at auction by People’s Bank for $3.5 million in 1992, and Sisti was sentenced to nine years in federal prison in 1995. A Lithuanian businessman bought it from the bank for $2.7 million in 1993, then reportedly faced bankruptcy himself — before selling in early 1996 to Mike Tyson for about $3 million.
The Tyson Era: Club TKO and a $22 Million Asking Price
Tyson had been released from prison in Indiana in March 1995 and earned $25 million in his comeback fight against Peter McNeely six months later. He poured money into the estate, adding a nightclub he called “Club TKO,” an indoor pool, a basketball court and an indoor racquetball court.
He also spent spectacularly elsewhere: $4.5 million on cars and motorbikes (19 vehicles bought for friends), $400,000 on pigeons and big cats, $300,000 on lawn care alone, and $240,000 a month in walking-around money. In May 1997 he listed the Connecticut mansion for $22 million — roughly $19 million more than he had paid a year earlier. There were no buyers.
In August 2003, Tyson declared Chapter 11 bankruptcy, listing $5 million in assets against $27 million in debt. That same year, his divorce from Monica Turner was finalised — and she received the Connecticut mansion. She almost immediately sold it for $4.1 million. The buyer was 50 Cent.
The 50 Cent Era: Cribs, Ferraris and Bankruptcy
Earlier in 2003, 50 Cent had exploded with “In Da Club” and “Get Rich or Die Tryin’,” which would sell 12 million copies worldwide. He spent millions on upgrades — a movie theater, a pool grotto, a helipad and a recording studio where he worked on “The Massacre” — and in 2007 gave MTV Cribs a tour of the house.
The tour is remembered for its car collection at the 13-minute mark: a Ferrari F50, a Ferrari Enzo and a Ferrari 599, in a house at number 50 on Poplar Hill Drive, spanning 50,000 square feet. But it has long been alleged that 50 did not own those Ferraris — Ferrari forum threads attribute them to a wealthy collector neighbour. The claim is unproven, but it fits the house’s pattern of appearances outrunning reality.
50 first tried to sell in 2007 for $18.5 million, without success, cycling the home on and off the market for years, typically asking $9,999,999. In July 2015, the curse struck again: he declared bankruptcy, listing $36 million in debts against $16 million in assets, and later described the house as costing nearly $70,000 a month just for maintenance and utilities. He finally unloaded it in April 2019 for $2.9 million — $1.2 million less than he paid, and $15.6 million below his original asking price.
The Curse Breakers?
The 2019 buyers were Florida businessman Casey Askar and his wife Shera, who made their fortune in fast-food franchises including Dunkin’. They used the estate as a summer and holiday retreat for their seven children, poured more than $3 million into renovations — a casino room, billiards room, fitness centre and more alongside the nightclub and studio — and in August 2025 listed it for $9.90 million (the listing was relaunched in August 2026).
At $9.9 million, the ask is more than three times what the Askars paid — though that comparison ignores their renovation spend and years of ownership costs. They do not appear to be in financial trouble, so perhaps the curse is broken. But buyers should beware: this house has ruined richer people than most.
Fellow rap mogul Snoop Dogg has kept his own property empire far steadier, while boxer Floyd Mayweather shows how even the richest fighters can find themselves in expensive legal tangles over money.
Sources and notes: Ownership history and prices per Celebrity Net Worth, Wall Street Journal, TMZ and Berkshire Hathaway HomeServices listing reports; room counts vary between reports and listing eras; Tyson’s purchase price is reported between $2.8M and ~$3M. Asking prices are not sale prices.
