The startlingly dark history behind Mike Tyson and 50 Cent’s former Connecticut mansion, now on the market for $10 million.

In the 1980s, Benjamin Sisti soared to prominence as the founder of Colonial Realty, a major player in the real estate sector. However, behind his lavish lifestyle and impressive properties lay a complex web of fraud that would ultimately lead to his downfall. This is the story of Sisti’s mansion, its subsequent owners, and the financial troubles that plagued them.

A Mansion Is Born

In 1985, Benjamin Sisti celebrated his success by constructing an extravagant 52,000-square-foot mansion set on more than 17 acres in Farmington, Connecticut, just a short drive from his company’s headquarters. Allegedly costing around $2.3 million at the time—equivalent to nearly $7 million today—the estate boasted luxurious features, including a private lake, a tennis court, and a guest house with four bedrooms. The main residence contained roughly 20 bedrooms and 40 bathrooms.

However, underneath this façade of luxury, Sisti was orchestrating a massive Ponzi-like scheme through Colonial Realty. The firm, which took in funds from investors while concealing its failing finances, ultimately deceived thousands, with many claiming to have lost their life savings. This scandal has been recognized as one of the largest real estate frauds in Connecticut’s history.

By 1990, both Sisti and Colonial Realty declared bankruptcy. Sisti claimed to possess just $15,000 in cash, and his opulent mansion slipped into foreclosure. In 1992, it was sold at auction for $3.5 million to People’s Bank. A year later, Sisti took a plea deal and was sentenced to nine years in federal prison.

Meanwhile, in 1993, a Lithuanian businessman acquired the mansion from the bank for $2.7 million, but by 1996, he faced financial difficulties and sold it to former boxing champion Mike Tyson for $2.8 million.

The Mike Tyson Era

In the midst of his own tumultuous journey, Mike Tyson had served time in prison following a rape conviction in 1992, but he made a triumphant return to boxing in 1995, earning $25 million in one match. Just months later, he purchased the Connecticut mansion.

During the next couple of years, Tyson earned around $155 million from just six fights, and he invested significantly in the estate. He added a nightclub named “Club TKO,” an indoor pool, a basketball court, and even an indoor racquetball court.

However, Tyson’s extravagant lifestyle eventually caught up with him. Within three years of his release from prison, he had spent exorbitant sums, including:

• $4.5 million on cars and motorcycles
• $400,000 on exotic pets
• $300,000 on lawn care
• $240,000 monthly for daily expenses
• $100,000 monthly on jewelry and clothing

In 1997, he attempted to sell the mansion for $22 million but found no buyers. By August 2003, Tyson declared Chapter 11 bankruptcy, reporting $5 million in assets against $27 million in debts. After finalizing a divorce from Monica Turner that year, she received the estate as part of their settlement.

50 Cent Takes Over

Monica Turner promptly sold the mansion for $4.1 million to rapper 50 Cent, who had skyrocketed to fame earlier that year with his hit single “In Da Club.” Following his acquisition, 50 Cent made numerous upgrades, including the addition of a movie theater and a pool grotto. In 2007, he famously showcased the mansion on “MTV Cribs.”

However, in 2007, 50 Cent also attempted to sell the home for $18.5 million, but faced difficulties. By July 2015, he declared bankruptcy, reporting $36 million in debts and $16 million in assets. He described the Connecticut mansion as a financial burden, costing nearly $70,000 monthly. Ultimately, he sold the property for $2.9 million in April 2019.

2019 – The Present

The latest owner of the mansion is Florida businessman Casey Askar, who purchased the estate after establishing himself in the fast-food industry, particularly through Dunkin’ Donuts franchises. Askar’s family recently listed the property for $9.9 million. They appear to be financially stable, which raises hopes that the mansion’s troubled history may finally be behind it. However, potential buyers should be aware of the estate’s complex and storied past.