Bob Stupak was the son of Chester and Florence Stupak. He was born in Pittsburgh, Pennsylvania. Chester Stupak ran a dice game called the Lotus Club in Pittsburgh for over 50 years. Stupak as a teenager was mainly interested in motorcycle racing, and once ranked third in the world after breaking a speed record.
As a young adult, Stupak moved to Australia to try to find his fortune. At the age of 21, Stupak lived in Melbourne and worked in the advertising industry.
While in Australia, Stupak was briefly married to Annette Suna, and they had a daughter, Nicole. From 1971 to 1985, Stupak was married to Sandra Joyce Wilkinson, and had two more children, Nevada and Summer.
Stupak moved to Las Vegas in 1971. He bought the Vault casino in downtown and changed its name to Glitter Gultch. He created a cowgirl sign named Vegas Vicki for the casino to compete with the Vegas Vic sign across Fremont Street at the Pioneer Club. Stupak acquired a small, 1.5 acres (0.61 ha) parcel north of Sahara Avenue at Las Vegas Boulevard South. On March 31, 1974, Bob Stupak's World Famous Historic Gambling Museum opened. "The name was about 10 ft (3.0 m) longer than the casino," Stupak recalled years later. On May 21, an air conditioner caught fire and the building burned down.
Two years later, Vally Bank's Perry Thomas loaned Stupak a million dollars to build the original Vegas World on the site of the former gambling museum. In 1979. Stupak opened Bob Stupak's Vegas World hotel and casino known for its promotions and the world's largest sign (which later blew down in a wind storm), and new twists on games, including the world's first quarter million and million dollar jackpot. At its peak in the mid-1980s, Vegas World grossed in excess of $100 million per year. In the meantime, Stupak donated $100,000 to the United Negro College Fund in exchange for a chance to play with the Harlem Globetrotters. He got his wish, and his appearance on the court in a Globetrotters uniform during one of their games shooting hoops made international news.
Then, taking a page from Donald Trump with his Trump board game, Stupak came up with his own board game he called Stupak after Trump declined his million dollar challenge for charity playing Trump: The Game.
In the mid-1990s, Bob Stupak was inducted into the Gambling Hall of Fame.
Stupak's unique promotions included the world's first one quarter million dollar jackpot followed shortly thereafter by the world's first million dollar jackpot. He also was wildly successful with his direct-mail marketing called the "Vegas Vacation Club" that enticed vacationers to Vegas World with what was almost a cost-free vacation package including room, meals, and vouchers for casino play. Participants returned year after year and spread the word until hotel occupancy was 100% year round.
In 1987, Stupak was considering the purchase of a local television station, as well as starting a weekly newspaper. In 1988, Stupak was the chairman of the newly formed Committee for Olympics in Nevada, and advocated for the Summer Olympic Games to be held in Las Vegas in 1996 or in 2000.
In 1989, Stupak won a widely publicized million dollar wager on Super Bowl XXIII. Later that year, he won the Deuce to Seven Lowball championship bracelet at the World Series of Poker and the Super Bowl of poker at Caesars Palace, both times edging out world-renowned lowball poker legend Billy Baxter for the championship. One of Stupak's most talked about promotions came when he paid a daredevil one million dollars to jump off the top of Vegas World, then charged him a $990,000 landing fee.
In 1990, Stupak approached the mayor and city council with a plan to build the largest free standing sign in the world. His plan was for an 1,800 foot tall neon sign that would tower over Las Vegas. Then-Councilman Steve Miller, an airline instructor pilot, convinced Stupak to redesign the structure to include an observation deck. Miller took Stupak for a flight over Vegas World in Miller's private plane. There they circled for over an hour at altitudes ranging from 1,000 to 2,000 feet watching the sun set. Stupak told Miller that to not share such a beautiful sight would be a sin, and he immediately went to work revising his plans to include a restaurant and amusement rides at the top of what was then to be called the "Stupak Tower." Stupak held a press conference and announced his plan with the caveat that his tower would be the icon of Las Vegas, and Steve Wynn's Mirage would be two miles from him, not the other way around. Within a year of Stupak's announcement, the construction on the tower began.
In 1995, Stupak suffered a motorcycle accident, breaking every bone in his face and going into a coma. Although the initial prognosis was that he would not survive, Stupak’s next of kin, son Nevada Stupak, approved a non-FDA-approved experimental drug to reduce the swelling to his head and brain. Stupak recovered, although with lingering health problems.
At the time of his motorcycle crash, Stupak was developing what had become known as Stratosphere Las Vegas, the largest structure west of the Mississippi and top 10 tallest structure in the world. The accident was only three weeks after Stupak agreed to bring in fellow poker player buddy Lyle Berman and his company Grand Casinos in as investors in the project, in large part due to the $550 million in capital they agreed to invest. This was Grand Casinos' big opportunity to enter the Las Vegas market due in large part to the overwhelming success in the Indian gaming market. Stupak called this the most difficult decision of his life as he had never had a partner and was always sole owner. The tower opened in late April 1996, making it the third most expensive casino development in history at the time; within a year Stupak was out as Chairman of the Board and the project ultimately ended as a financial disaster. Stupak lost nearly $200 million personally. Stupak continued to plan Vegas projects, including a purchase of the Moulin Rouge Hotel and a huge hotel shaped like the RMS Titanic, but these endeavors never bore fruit.
Stupak appeared in the first season of the GSN series High Stakes Poker. He also appeared at a final table during the first season of the World Poker Tour.
As of 2008, his total live tournament winnings exceeded $865,000. With his World Series of Poker Bracelet in the Deuce to Seven Championship and his wife Sandy in the Casino Owner’s Championship at Binion's Horseshoe, they were the first husband and wife combo to hold WSOP bracelets.
Stupak ran for Mayor of Las Vegas twice. In 1983, Stupak ran against then-current Mayor William H. Briare, as well as six other candidates. Stupak came in second place, with 33.1 percent of the vote, losing to Briare, who attained 62.5 percent and won re-election.
Stupak ran for Mayor again in 1987, and clashed often with the media. During the campaign, Stupak released financial documents which indicated his net worth to be over $54 million. Stupak almost succeeded in being elected Mayor. After defeating a dozen other candidates in the primary, Stupak forced an incumbent city council member into a runoff general election contest. Following what many believed was a tampered vote count, Stupak lost the election. The day after the election, the Las Vegas City Clerk apprised her boss the City Manager of her and her staff's concerns that the computer results were skewed and Stupak had actually won the election. The Clerk was immediately terminated after serving as the Chief Elections Officer of the City of Las Vegas for over 17 years. Based on the Clerk's statements, Stupak paid $17,000 to have the punch card ballots recounted. During the weeks leading up to the recount, the Registrar of Voters purchased thousands of new ballots from the out of state printer and had them delivered to a county warehouse in East Las Vegas. Reporters staked out the warehouse and one evening photographed a dozen women enter the building at dusk and exit at dawn. Pizzas were delivered. Several days later, the recount took place and the punch card ballots exactly matched the final vote tally from the computer. Two days after the recount, thousands of ballots were illegally shredded then discarded in garbage bags on the loading dock of the Registrar's warehouse. Several bags were recovered by reporters and dozens of ballots taped back together. Those ballots bore the date of the 1987 municipal general election Stupak lost. The shredding violated state and federal laws that require all voted ballots be preserved for two years in the Registrar's vault. When the story made front page news, the Clark County District Attorney launched an investigation followed immediately by the resignation of the Registrar of Voters. After his cursory investigation, the DA found no probable cause to prosecute, so the case was closed. However, the ousted City Clerk sued the city for wrongful termination and won. During years of litigation in US Federal Court, the former Clerk and several of her Deputy Clerks testified about irregularities they observed during the 1987 mayoral vote tabulation.
In 2006, Stupak unsuccessfully ran as a Democrat for Lieutenant Governor of Nevada.
Stupak died of leukemia on September 25, 2009, at the age of 67.
In February 2016, the Las Vegas Planning Commission and the Las Vegas City Council unanimously approved the renaming of one block of Baltimore Avenue as Bob Stupak Avenue. The renaming occurred on Stupak's birthday, April 6, 2016, as part of a 20th anniversary celebration held for the Stratosphere on the property's north side, near the corner of Baltimore Avenue and Las Vegas Boulevard.
A community center and a park named after Stupak are located near the Stratosphere. The community center was opened in 1992, and was demolished in 2010, to be replaced by the new Stupak Park. A new Stupak Community Center was opened on January 4, 2010. The new facility is 34,183 square feet and cost $7.5 million to construct. The community center celebrated its 25th anniversary in January 2017.