Jack Ranallo: Where is the Fraudster Now?

Investigation Discovery’s ‘Who the (Bleep) Did I Marry? Forgive and Forget / Field of Schemes’ chronicles how serial fraudster Jack Ranallo committed fraud in Cumberland, Rhode Island, in the latter half of the millennium’s first decade. Under the pretense of running a fake junior baseball academy, he swindled thousands of dollars from the parents of his minor players. If, you’re interested in discovering more about Jack Ranallo, and how he was caught, here’s what we know.

Who is Jack Ranallo?

In early 2000, Jennifer Ranallo was a single mother supporting herself and her three sons and was getting used to being on her own again. She spotted an intriguing stranger — Jack Ranallo — at her Rhode Island shopping mall. She recollected how she was at the shopping center with one of her children, and Jack was behind her, talking about music to one with his friend. She recounted, “He said something that interested me, and I turned behind and struck up a conversation.”

Jack introduced himself as a music licenser from Baltimore, Maryland, who was in town to attend a conference. Jennifer was instantly attracted to the elegant and polite gentleman, and he gave her his email address before they parted. Over the following months, they exchanged flirtatious correspondence, and Jack stated he owned his music licensing business. However, he remarked his true passion was baseball, and he used to play in AAA leagues. He claimed he was a promising pitcher but had to stop due to a devastating injury.

The couple married in April 2001. One of her sons, Josh Gaudette, recollected, “I loved how Jack was very easygoing, and my mom was deeply in love with him.” His business flourished as he worked long hours from their Cumberland, Rhode Island, home basement. She trusted him with the household finances and even put his name on the house deed. Jack told her he would pay the monthly mortgages and take care of the bills, and she did not need to be worried about anything.

By 2004, his business seemed to take a hit, and money seemed tight. Jennifer went to work again while Jack focused on his old passion of playing baseball. He jumped at the opportunity to work with a local junior baseball team in April 2006. A few months later, Jack proposed to open a baseball academy. Jennifer received a call from the bank in November 2007. The bank operator told her Jack had written two $10,000 checks to her account, which Jack explained was because of things going wrong with the academy.

While she forgave his excuse for committing forgery, the authorities arrested him for paying with bad checks. Jack was out on bail, but the investigators decided to run a background check to discover he had several aliases (Jack Ranallo, Jack Dorvis, Jack Norris) and a prior criminal record of financial scams and petty theft. Jack was arrested in November 2011, and court documents stated he fraudulently portrayed himself as a former minor league baseball player with official ties to the Baltimore Orioles between April 2007 and February 2008.

Where is Jack Ranallo Now?

Jack fraudulently solicited and obtained funds from families by lying about establishing a baseball academy and an elite summer league team with the full backing of the Orioles. He had even implied that his relationship with the organization would help the players get scouted. Ten families paid $31,500 for the supposed operation of the elite baseball team that would play up to 80 games during the summer with other elite teams. He also obtained “short-term loans” from two victims, with the funds to be held in escrow totaling $45,000.

Jack was sentenced to six months for contempt of court after he kept lying about his medical condition to postpone his trial. While in prison, his former wife, Jennifer, learned that Jack had not paid any utility bills for nearly five years. Court records stated he never played minor league baseball and used the money for personal living expenses. He used a substantial amount to pay his mortgage payments hours before his home was scheduled to be auctioned at a foreclosure sale.

According to the episode, Jack had a prior record of committing fraud — landing in trouble in Florida in 1983 for petty theft and in Maryland in 1999 for running a fake baseball academy. He pled no contention to obtaining money under pretenses, bad checks, and filing false documents on December 6, 2011. The court sentenced him to 15 years, with two and one half to serve, with the remainder suspended with probation on January 9, 2012. He was also ordered to pay restitution to the victims.

Attorney General Kilmartin said, “Jack Ranallo preyed on every little leaguer’s dream of one day playing for the Majors. Delusions of grandeur and greed were at the core of his elaborate scheme to con hardworking families out of tens of thousands of dollars for his personal use. Thanks to the families for coming forward and the investigative efforts of the Rhode Island State Police, Jack Ranallo has finally struck out.” He was also arraigned in Sixth District Court on January 12, 2012, on a Rhode Island State Police complaint.

Court records state he was charged with one count of obtaining money under pretenses over $500 and a misdemeanor charge of providing a false document in an alleged con to defraud a Kentucky family of nearly $100,000 in a Kentucky land deal scheme. Jennifer, now divorced from Jack, lives in Cumberland and works two jobs to pay all the debt Jack landed her in. Jack is still in California, serving his probation under the strict eyes of the authorities and paying restitution to his victims.

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