Local News

Million Dollar Con Artist Behind Bars Again

(Michigan City, IN) - Luck appears to be running out for a long time con artist who apparently went gambling with piles of money swindled from his victims.  Timothy J. Bailey, 53, of Michigan City is being held without bond in the Yell County Jail in Arkansas.


On March 11, he was given a five-year prison sentence for level 4 felony Securities Fraud and other theft related counts in La Porte Superior Court 1.  He was ordered to report to the La Porte County Jail the next day to begin serving his sentence but failed to show up.


According to La Porte County Police, members of the Fugitive Apprehension Street Team on Sunday gave authorities in Arkansas his possible whereabouts, obtained from an anonymous source.  Bailey was taken into custody the next day, police said.  He will be transported to the La Porte County Jail at a later date to begin serving his prison sentence, police said.


According to court documents, a vast majority of the money Bailey stole was slightly over $1 million from a Trail Creek couple.


In 2018, Bailey posing as a legitimate businessman at a real estate seminar in Chicago talked the couple into giving him money to purchase and renovate houses in the Michigan City area.  He later persuaded the couple to give him additional funds to construct new homes on empty lots in Florida, according to court documents.  In exchange, he gave them promissory notes pledging to pay back the money with interest and give them a percentage of the profits.  The couple began receiving what appeared to be dividends but the checks bounced, court records disclosed.  They also paid a visit to the listed development site in Florida to find no evidence of any construction.


According to court documents, a track of Bailey’s financial accounts revealed more than $200,000 of the stolen money was withdrawn at casinos and ATM’s near casinos.


Bailey has a level 6 felony charge of Check Fraud still undecided in La Porte Superior Court 4.  He also has a long history of prior convictions for crimes like Theft, Counterfeiting, Check Deception and Home Improvement Fraud, according to court records.

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