The Criminals & Culprits of Jeopardy! Part 1: Blood Loss, Burglaries, & Murder Mysteries
From embezzlement and fraud to vandalism and potential murder, these eight players had their 15 minutes of fame and 15 minutes of shame.
When we think of people involved with Jeopardy!, we tend to resort to the most iconic and memorable winners: Amy Schneider, Mattea Roach, James Holzhauer, Matt Amodio, Julia Collins, Brad Rutter, and current host Ken Jennings. We also derive from Ken Jennings in thinking of former hosts such as Art Fleming, Alex Trebek, Mayim Bialik, and even the short-lived run of episodes officially hosted by Mike Richards in the first week of Season 38.
Among the thousands of players who have appeared on the show through the show’s decades-long history of airing on TV, however, there is a very small collection of players who became well-known for infamous and often deplorable acts that they partook in after, or even before, their appearance on the show. These transgressions range from the likes of cyber crimes, fraud, assault, murder, and even sexually-based offenses. I scavenged as much online info that was available to the fullest possible extent and was able to acquire many names. So many names, in fact, that I had to split this into two parts!
The analysis of each of these players was carefully ordered to fit the magnitude of the crimes they were either convicted or alleged of doing. Their significance to the TV show and its lore was also factored into where they were placed. The more egregious acts of delinquency will be saved for the second half of the article so that all viewers will have breathing room as we go along. So now that I’ve given you a short summary of what to expect, let’s get right into the list, starting with our first entry.
1.) Jeff Kirby
Most contestants on Jeopardy! only appear on the show once. Most contestants lose their first game and never appear on the show again. In uncommon but not particularly rare cases, some players will lose a game through a circumstance out of their control or through the fault of another party, such as multi-day champion Ryan Fenster following a questionable ruling which affected the outcome of his fifth game. In the case of Jeff Kirby, however, he appeared on the show twice with his second showing taking place one decade following his original appearance. He even wore the exact same tie as before. How did this happen, exactly? To tell this story, we have to appease our king Prince and our queen Charli XCX by going back to the tail-end of 1999.
On December 8th of that year, Jeff Kirby, an elementary school teacher hailing from Santa Maria, California, appeared as a challenger against reigning 2-time champion Sam Raman and challenger Amanda Folk. While he had a solid showing in the first round, garnering $2,500 compared to Amanda’s $3,100 and Sam’s $900, he found himself shut out in most of the Double Jeopardy! round, only gaining $200 and going into Final Jeopardy! locked out in third place by Amanda. Despite him and champion Sam responding correctly on the final clue, Jeff finished in third place, taking home a digital camera creative kit as consolation. Amanda won the game with $7,800 but proceeded to lose the next day.
Given the low scoring game he had set and the timeframe of which he appeared on the show, Jeff’s chances of returning onto the show were slim to none. Now let’s fast forward to ten years later. It’s Monday, October 12th, 2009 and champion Terry Linwood is on a roll with two wins and just under $50,000 in earnings. His opponents are Emma Span from Brooklyn, New York, as well as… Jeff Kirby? From Saint Maria, California? A math and science teacher? Yes. Without explanation, Jeff Kirby reappeared as a contestant ten years later. He lost in a runaway in his first game and wasn’t incorrectly ruled on anything that would have affected the outcome of the game. So what was he doing there?
Well, there’s one thing we could give him in his second appearance: his gameplay was much better. He kept up very well with the reigning champion, with the lead for Final Jeopardy coming down to the wire. Despite holding a $2,700 lead over Terry, Jeff rang in on the last clue worth $2000, answering incorrectly and leaving his lead wide open for Terry to take back… which is exactly what happened, with Terry responding to the same clue correctly. The $4,000 swing gave Terry a $1,300 lead over Jeff going into Final Jeopardy!, in which Terry was also the only player to respond correctly, adding $16,301 to his score for a winning total of $33,901 and a 3-day total of $83,303. Terry went on to become a 5-time winner and qualifier for the 2010 Tournament of Champions, where he finished as a semifinalist for $10,000.
Following Jeff Kirby’s second appearance, longtime Jeopardy! fans across the internet immediately took notice of Jeff’s repeat appearance, including the Sony Pictures message boards of the 2000s. Notably, the game thread was one of the most discussed games of the month, and the backlash was so immense that the producers of Jeopardy! wound up making a thread addressing the error:
Despite the relatively quick transparency regarding the situation, some fans were… not particularly impressed with this response. So in the end, Jeff Kirby did not receive his second third place consolation prize, which in this case was $1,000. He wasn’t arrested or criminally charged or anything, but he did commit arguably the funniest violation of the show’s rules in its history. We can only wonder if he still wears the tie to this day.
2.) John Ferraro
The next player on our list is Florida man John Ferraro, a 1-time champion from 1992. A couple of years prior to his appearance, Ferraro pleaded guilty to embezzling approximately $10,000 from Macy’s when he worked as a part-time employee from 1987 to 1989. He did this by falsifying his time sheet with authorizations of overtime and vacation time, according to chief assistant prosecutor Randolph Subryan. Upon realizing that he would lose his teacher’s certificate and pension before resigning, he withdrew the plea in April of 1990, according to Seattle Times. He applied for a PTI in January of 1991 to the state of NJ in order to help subdue the charges, but had his heart broken on Valentine’s Day when he was denied. Despite the case being in the developmental process, he went out of his way to apply on Jeopardy! anyway, making it onto the show in the first month of 1992, where he won one game worth $6,700 before losing to 4-time champion Walter Mayes. This is approximately 33% less than the amount of money that he embezzled from Macy’s.
I know there’s an incentive here to make the joke that these former players landed themselves in “jeopardy,” but in the case of Ferraro, his appearance on the iconic game show actually did land him in direct peril when he was noticed on television by Robert Greco, a detective who was investigating him in Passaic County, New Jersey. While it was a shock to Greco, supervising producer Rocky Schmidt expressed even more shock and took action with the rest of the production team in making sure that Ferraro would not receive his winnings. Ferraro traveled from Florida to New Jersey to appear in court the week following his game show appearance, which was covered by Deseret News. Superior Court Judge Frank M. Donato said Ferraro appeared to show no regret and attempted to distribute the blame to another supervisor. He was then ordered to stand trial in the same county of New Jersey, in which his disposition was held on February 20th, 1992. It wasn’t until April 2nd, 1992 when his sentence was given. He was ordered to 3 years of probation and 100 hours of community service under the statute of “theft by deception.” He has not had any run-ins with the law ever since.
3.) Ian Norris
Ian Norris appeared on the show as a challenger against Beth Stewart, who had one win at the time and just under $40,000 after defeating 3-time winner and 2021 TOC alternate Elise Nussbaum. While he got off to a quick start, he lost a good deal of money in the second half of the first round and overall put up a pretty forgettable performance. He finished in second place after being locked out in a runaway from the champion Beth, taking home $2,000. According to some documents, however, he may have taken a lot more than $2,000 in an act of insurance fraud with his company, Sabal Insurance Group, Inc.
On January 7th, 2015, four years before his Jeopardy! appearance, Norris was arrested on grand theft charges, with the corporation itself also being summoned to face criminal charges. Ian and the company were investigated by the Miami-Dade Aviation Department on suspicions of overbilling and defrauding the department and its vendor, Quality Aircraft Services, Inc. The investigation apparently uncovered fraud that violated MDAD policies issued back in 2006 and 2007. Sabal apparently overbilled QAS for those regulations and retained the monetary difference in premiums. Notably, QAS and MDAD hadn’t retained a management agreement with each other since 2010 by the time the charge against Norris was filed.
According to the Sun Sentinel, Norris stated the case was sealed and charges dropped once Norris agreed to pay $300,000 in a settlement, with $180,000 going to the Miami Aviation Department, $100,000 toward a victims’ fund, and $20,000 going to the investigation. Four years later, three months before his game show appearance, Norris filed against his corporate liability insurer, Philadelphia Indemnity Insurance Co. However, the 11th Circuit U.S. Court of Appeals ruled that ill-gotten gains weren’t covered under the insurance policy, obviously leaving Sabal in a non-affirmative position. Despite all of this, it had no real effect on Ian Norris’s participation on Jeopardy! and is ultimately the least consequential entry on this list.
4.) Geoffrey Zimmerman
On November 26th, 2001, the game of Jeopardy! as we know it changed fundamentally when the dollar values of the clues were doubled in both rounds of the game, providing a selection from $200 to $1000 in the first round and $400 to $2000 in the second round. It’s also the game that introduced us to a controversial lawyer from Toronto, Canada known as Geoffrey Zimmerman… not to be confused with this guy. Geoffrey was one of three new players to appear in the game following Trevor Norris winning his 5th game and retiring undefeated. The game itself was quite sloppy, with a Combined Coryat of $17,200 being posted from the three players with the leading player, Harold Skinner, running away with the game just barely at the five-figure mark. As the lone solver of Final Jeopardy, Geoffrey finished the game in second place with $7,600, just $100 less than Harold’s winning score of $7,700. Geoffrey won a trip to Italy as a result of finishing in second.
Zimmerman formed a business relationship with Signe and Robert McMichael, a Canadian art collector and philanthropist, back in the 1980s. The McMichaels both founded the McMichael Canadian Art Collection, an art museum located in the village of Kleinburg. The permanent collection of art materials were made exclusively by Canadian artists, and it was also one of the only museums in Canada to contain art made by Indigenous people of Canada. Zimmerman was appointed as Signe McMichael’s representative on the board of the Collection after spending the mid to late 1990s as a member. Robert McMichael passed away in November of 2003, which resulted in Zimmerman becoming the trustee for the estate until Signe McMichael’s death.
He was later alleged to have kept a lot of the funds for himself, with unauthorized and other payments of impropriety being made at the account of Penny Fenwick, the niece and executor of the case that was building against Zimmerman. According to The Globe and Mail, this included a $3,800 cell-phone bill and $0.90 for a parking meter. He allegedly paid himself $450,000 without keeping any proper records of his compensation, as well as without the consent of the beneficiaries, according to the Orlando Reports. Once Mrs. McMichael passed in 2007, a lot of these details began coming to light. Zimmerman was once a lawyer that the McMichaels could count on for their biddings, but then it quickly devolved into greed once they both passed. The case Fenwick filed against him bluntly stated that he “used the trust to further his own personal and financial interests” and completely went against the wishes of the McMichaels. According to The Globe and Mail, Zimmerman ignored many of the court orders and hearings, blaming his absences on social anxiety, depression, and substance abuse. Zimmerman was dropping lawyers for his case one by one as his conditions seemed to worsen over time, and so did the monetary damage as millions of dollars went missing between 2003 and 2009.
On October 8th, 2010, National Post reported that he must repay $1.1 million of trust money to the McMichael estate, with $390,000 being amounted to personal expenses. His behavior was described as “appalling” and “irresponsible” by the judges of the case, although he was not expected to face any disciplinary proceedings. Four months later in February of 2011, however, the story took a shocking and dark turn when Zimmerman was found dead at the age of 52. His cause of death is unknown, though it leads me to wonder whether his illnesses he proclaimed to have to the court holds any weight. He left behind a wife, two kids, and the rest of his court orders. Despite the sudden news, Upkar Arora, chair of the gallery’s board of trustees, asserted that plans regarding the collection of money from Zimmerman’s estate would be recouped for by Fenwick’s lawyers. As reported by The Star, Arora said that they were still digesting the news and that it wasn’t the time. As of 2017, Arora is still a trustee of the art collection, but it’s unknown and unlikely that the funds pocketed by Zimmerman were ever recovered.
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