In June 1996, Colombo's father-in-law, William 'Buddy' Fisher, cashed in a stolen $1 million Monopoly piece.

Investigations later indicated that Jacobson had admitted to sending the winning piece to the hospital. Game rules prohibited the transfer of prizes, but McDonald's chose to follow through by treating the $1 million as a donation to the hospital, making the final $50,000 annuity payment in 2014. Jude Children's Hospital in Memphis, Tennessee, received an anonymous letter postmarked Dallas, Texas, which contained a $1 million winning game piece. In 1995, Colombo appeared in a nationally televised McDonald's commercial promoting his (fraudulent) win of a Dodge Viper. Jacobson sold winning pieces for a percentage of the winnings in advance, initially to friends and family but expanding nationwide after a chance meeting in the Atlanta airport between him and Gennaro 'Jerry' Colombo of the Colombo crime family. He began stealing winning game pieces after a supplier mistakenly provided him a sheet of the anti-tamper seals needed to secretly make the swap. Jacobson justified his long-running multi-million-dollar crime as being his reaction to executives re-running randomized draws to ensure high-level prizes went to areas in the United States rather than Canada – though he did not take the stolen pieces to Canada to rectify this supposed problem, choosing instead to personally gain by selling the pieces. Jacobson was able to remove the most valuable game pieces, which he then passed to associates who would redeem them and share the proceeds. A subcontracting company, Simon Marketing (then a subsidiary of Cyrk), which had been hired by McDonald's to organize and promote the game, failed to recognize a flaw in its procedures. promotion was halted after fraud was uncovered. As a result of it being postponed, the stickers for that year's promotion had incorrect dates, as they were originally printed the year prior. Instead, the same promotion 'Monopoly VIP' was instead run in 2021. In 2020, in the UK, it was intended to run in March that year, but due to the COVID-19 pandemic, the promotion was postponed. In 2019, Deputy Leader of the UK Labour Party, Tom Watson, said that the Monopoly promotion was a 'danger to public health' and urged McDonald's to drop the 'grotesque marketing strategy'. In 2015, the Monopoly game was replaced in the US by 'Game Time Gold', using an NFL theme.

McDonald's had a relationship with Simon Worldwide Inc., which was responsible for the distribution of the contest pieces and the awarding of major prizes. Laws generally forbid a company from administering its own contests, in order to prevent fraud and to ensure that all prizes are given away as a result, such promotions are handled by an impartial third-party company. Like many merchants, McDonald's offered sweepstakes to draw customers into its restaurants. version, and later in the Canadian version. From 2003 to 2009, Best Buy was involved in the U.S. Argentina and Brazil were included in 2013 as well as South Korea in 2014 and Ireland in 2016. The promotion has been offered in the United States, Canada, Australia, Austria, France, Germany, Hong Kong, the Netherlands, New Zealand, Poland, Portugal, Romania, Russia, Singapore, South Africa, Spain, Switzerland, Taiwan, and United Kingdom since 1987.

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