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The wealthy widow of a pioneering Roblox programmer has accused a New York City escort of manipulating her into paying him $6 million so they could have an 'exclusive' relationship.
Marianne Flippo, 49, launched a lawsuit in Manhattan Supreme Court on Monday suing gigolo Greggory Starr, 38, for allegedly 'taking advantage of a grieving and ailing widow to the tune of $5.95 million.'
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Flippo → see → million
The complaint, obtained by the Daily Mail, claims that Starr 'enacted a ruthless plan to steal millions of dollars' from Flippo while she was in a vulnerable state.
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she → obtain → state
Flippo said she was on strong opioids following surgery, and was still grieving the loss of her husband of 28 years, Roblox programmer Chad Flippo, when Starr convinced her to pay his agency millions of dollars to free him from his contract.
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Starr → say → contract
The pair had struck up a relationship after Flippo paid Cowboys 4 Angels (C4A) male companion agency $27,000 for Starr's translation services during a vacation to Italy in December 2024.
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Flippo → strike → December
However, as their 'love' developed, Starr and his agent, Bridget Collins, told Flippo that she needed to pay $10 million in order for him to 'escape' his escort duties at C4A and become her exclusive boyfriend, according to the complaint.
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him → develop → complaint
Flippo claimed in the lawsuit that she was 'pressured by Starr and Collins' to sign an 'exit agreement' to pay $5.95 million while 'still emotionally lost due to the loss of her husband' during a trip to Atlanta, Georgia in February this year.
She claimed that they convinced her to drink booze before signing Starr's 'exit agreement', and that she was impaired by 'multiple prescription medications as well as five alcoholic drinks' at the time.
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she → claim → time
Marianne Flippo, 49, launched a lawsuit in Manhattan Supreme Court on Monday suing gigolo Greggory Starr, 38, for allegedly 'taking advantage of a grieving and ailing widow to the tune of $5.95 million'.
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Flippo → launch → million
Flippo is pictured with Starr at a mansion party in New York City in December
New York City escort Greggory Starr, 38, has been sued by a grieving widow who claims he manipulated her into sending almost $6 million in funds to become her 'exclusive' boyfriend
Flippo's lawyer, Larry Hutcher, also stated in an affirmation obtained by the Mail that she was suffering with 'Stockholm syndrome' and that Starr had a 'Svengali-like control' over her.
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Starr → picture → her
The Daily Mail has reached out to Starr for his side of the story.
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Mail → reach → story
He did not return phone calls or messages in time for publication.
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He → return → publication
Flippo's lawsuit outlines how she lost her childhood sweetheart and husband of almost three decades, Chad Flippo, 'to the horrors of depression' when he took his life on August 5, 2024.
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he → outline → August
Chad was 'an extremely successful computer programmer who made a fortune programming for, as well as creating and patenting inventions related to, the popular online game Roblox', and his widow inherited a 'large fortune' when he died, according to the complaint.
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he → make → complaint
However, his sudden passing 'devastated Marianne and shattered her world' and she 'understandably struggled to cope with the loss', according to the lawsuit.
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she → devastate → lawsuit
Her struggles were also 'exacerbated' by 'Ehler-Danlos syndrome', a disease which impacts the body's connective tissues and limits life expectancy to around 50 years old.
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which → exacerbate → years
It also increases sensitivity to alcohol and medications.
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It → increase → alcohol
Four months after her husband passed, Flippo decided to take a trip to Italy but was 'nervous about traveling internationally', according to her complaint.
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Flippo → pass → complaint
One of Chad's former colleagues reached out to C4A on her behalf, and the agency paired her with Starr, an Italian speaker who could 'assist her on the trip'.
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who → reach → trip
Flippo said she was not aware that C4A was an escort service at the time, and she hired Starr 'purely for assistance on her trip', according to the complaint.
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she → say → complaint
New York City escort Greggory Starr, 38, has been sued by a grieving widow who claims he manipulated her into sending almost $6 million in funds to become her 'exclusive' boyfriend
Flippo and Starr are pictured with a friend at a New York City mansion party in December 2025
'During the trip, Starr had his own room and while he did make advances to Marianne she turned him down because she was still mourning Chad,' the lawsuit states.
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lawsuit → sue → Chad
Flippo paid C4A $27,000 for Starr's services on the trip, and did not have any contact with him after returning home until C4A began calling her, according to the complaint.
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C4A → pay → complaint
The widow claims that C4A employees including Collins started calling her to tell her that 'Starr missed her and wanted to talk to her'.
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Starr → claim → her
Flippo agreed to meet with Starr, and, sensing her 'vulnerability and knowing of her wealth', he 'began to worm his way into her life', the complaint claims.
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complaint → agree → life
'After Starr firmly had Marianne hooked, he convinced her to continue paying C4A to spend more time with him,' the lawsuit alleges.
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lawsuit → have → him
He then 'insisted' that she wire C4A $150,000 so that he could date her 'exclusively'.
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he → insist → her
Flippo said she was 'swept up by Starr's whirlwind of affection' and 'agreed to this contract'.
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she → say → contract
As their relationship developed, Starr 'further ingratiated himself into Marianne's life and psyche, and ultimately made her dependent on him', the complaint alleges.
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complaint → develop → him
Meanwhile, Collins also 'wormed her way into Marianne's life and convinced her that they were friends' in order to 'manipulate' her, according to the complaint.
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they → worm → complaint
Flippo claimed that Starr 'began acting oddly' in the summer of 2025, and admitted that he had been seeing an ex-girlfriend, prompting her to break up with him on October 1.
'This should have been the end of the situation, but C4A and Starr would not let Marianne and her money go,' her complaint alleges.
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complaint → claim → situation
Collins and her assistant 'repeatedly' contacted Flippo and tried to convince her to meet with Starr, the lawsuit claims.
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lawsuit → contact → Starr
They told her that 'Starr loved her, was sorry, and wanted to get back together with her', per the complaint.
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Starr → tell → complaint
The Daily Mail has reached out to Starr for his side of the story.
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Mail → reach → story
He did not return phone calls or messages in time for publication.
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He → return → publication
He is shown in a photograph from his Instagram account
New York City escort Greggory Starr, 38, has been sued by a grieving widow who claims he manipulated her into sending almost $6 million in funds to become her 'exclusive' boyfriend
The widow claims that Starr 'wove a web of emotional manipulation' which 'ensnared' her, 'with the goal of taking her money'.
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which → show → money
Flippo's lawsuit adds that while 'still in a vulnerable state', she 'eventually gave in and agreed to meet with Starr' in November 2025, when the escort allegedly 'forced her to get back together with him' through manipulation.
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escort → add → manipulation
Starr moved into her apartment on December 1, 2025, and asked her to sign another contract with C4A so that they could be together 'full time', per the complaint.
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they → move → complaint
Flippo said she wired $368,000 to be with Starr exclusively from this date through May 2026.
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she → say → May
In early 2026, she traveled to Los Angeles for surgery, and in the aftermath, she had to take strong drugs, including gabapentin and codeine, a narcotic.
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she → travel → gabapentin
Combined with her Ehler-Danlos syndrome, this put her in a 'compromised mental state', according to the complaint.
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this → combine → complaint
She also suffered 'from a severe infection in her arms' which required even more medication, the lawsuit states.
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lawsuit → suffer → medication
It was during this 'time of vulnerability' that Collins told Flippo that it would take $10 million to free Starr from his contract, and that she was his 'only way of escaping C4A'.
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she → tell → C4A
…and 14 more, not listed.
The Aporia
