John George could take the most mundane of situations and create entertainment. All he had to do was place a bet.
Everything was fair game — the sex of his daughter’s first child, the first person to pick up a torn dollar bill he placed on an airport baggage carousel or the willingness of an employee to jump into a scum-covered swimming pool.
John’s life was marked by an unbroken string of bets, and he believed he could beat the odds.
“He was always waiting for that big one,” said his daughter Sue Shaw, 53.
John, 78, of Dubuque, died in late March of complications stemming from multiple chronic health conditions.
His primary motivation in life was admittedly money, and he worked hard to obtain it. As a young boy in Dubuque, John sold Kool-Aid, washed cars and mowed lawns.
He started J & J Tree Service in 1972. After constructing a swimming pool in his backyard, he founded J & J Pools & Spas in 1977. John could peddle anything, including dirt, which he started selling in 2000 as a separate venture.
The risk-taking, persistence and ingenuity that made John an accomplished businessman were also traits that lent themselves to gambling.
In a self-published autobiography, John recalled his first bet, which he placed at the age of 5 or 6.
“I was playing along the railroad tracks with some other kids one day and one of the kids bet me 50 cents that I couldn’t roll under the moving freight train and lie between the tracks on my back and get out before the caboose came,” John wrote. “I took the bet, and I won. Not that I was brave, but it was because I didn’t have 50 cents to pay him off if I lost.”
As a young man, he spent Friday nights speeding on a collision course with other cars while playing games of “chicken,” earning $20 to $50 every time he won. He earned the nickname “Crazy George.”
John viewed his success in gambling as a bet on himself — that he could “beat the system” while doing something he enjoyed.
He set up a personal casino in his basement, featuring a blackjack and craps table and three slots. His then-8- and 9-year-old daughters played the part of waitresses, ferrying cocktails to his party guests.
“We made aprons that said ‘tips’ on it,” said his daughter Jennifer Neuhaus, now 52. “Just in case they forgot.”
John was an initial investor in Diamond Jo Casino and visited the establishment frequently, feeding its slot machines with coins.
He took gambling on the road, too, traveling to riverboat casinos in Davenport and Bettendorf, Iowa, to Native American-owned establishments in Minnesota and, every winter, to the champion of all destinations — Las Vegas.
John was a high-roller, regularly staying at hotels for free, with food and beverage service comped.
In an interview with the magazine “Midwest Gaming & Travel,” John said he earned $250,000 the previous year — an accumulation of midsize jackpots on the $1 and $5 slot machines.
What he did not acknowledge were his losses, his family said.
“There ain’t no beating the system,” said his son, Toby George, 56.
For the most part, John’s gambling did not trouble his kids, who were accustomed to it from an early age. But later in life, Sue said, his frequent trips occasionally bothered her.
“I think he missed out on (seeing) the grandkids more that way,” she said.
The financial stress caused by his gambling ended John’s marriage in 2001.
“He always thought he was going to make more,” Jennifer said. “Whatever I got in my pocket I can lose because there will be more tomorrow.”
Just as important to John was putting on a show. His family fondly recalled his antics, a reliable source of amusement.
Once, a friend bet John $100 that he could not drive his car backward on a one-way street, moving with the flow of traffic in reverse. The route passed the Dubuque Police Department along Central Avenue.
To avoid detection, John waited until a semi-tractor trailer drove between the station and himself and creeped alongside the vehicle.
On a different occasion, he drove a moped through the former Finale Lounge.
“Some kid was at the stoplight right there,” Jennifer said. “So, Dad gave the guy 20 bucks and took the moped and rode it into the bar.”
Sometimes John faced unpleasant repercussions.
During an event in Dubuque, the cops were called after John stood atop a chair and dove into a pyramid of plastic cups. Sue, home from college, visited the police station in a failed attempt to bail her father out of jail.
John recounted his escapades in his autobiography, “Rags to Riches to Rags,” then marketed the book to Gamblers Anonymous.
John’s health began to decline during the final five years of his life. He suffered from diabetes. An accident that left him pinned under a riding lawn mower further compromised his health.
When it became apparent John could no longer care for himself, he moved into a nursing home where he spent his final six months, unhappy while living under the lockdown prompted by the COVID-19 pandemic. Without company or a friendly bet, his family said, he lost the will to live.
“I used to joke that my worst fear was dying and still having some money left,” John wrote in his book.
But if there is gambling behind those pearly gates, Toby said, John is probably kicking himself for not saving a little money for his heavenly journey.