However, it took until 1984 before the current US president made his first breakthrough into the industry. He helped to build a $210 million establishment in Atlantic City, which was renamed Trump Plaza soon after opening.
Additional Atlantic City casinos followed for Trump, while the New Jersey location also became the capital of boxing in the 1980s. Mike Tyson fought four times at Trump Plaza across 1985 and 1986, while defending his heavyweight titles a further four times in the city later in the decade.
Then in February 1990, Tyson headed to Japan to put his belts and 37-fight perfect record on the line against James ‘Buster’ Douglas. It was a fight he unexpectedly lost in the 10th round.
Also in Tokyo to promote the fight was Trump, whose casino ventures at the time could profit from a shot in the arm. At a party the night before the Tyson fight, a person to provide both publicity and access to a wealth of cash he was willing to gamble was another in attendance.
Akio Kashiwagi was regarded as one of the best five baccarat players in the world and was well known within the industry for rinsing $20 million from a casino in Australia. His assets were deemed to be worth in excess of $1 billion.
Trump wasted little time negotiating a game at the Trump Plaza that was lucrative enough to entice The Whale into making another overseas trip.
The visit soon followed, with Trump laying on the penthouse and Kashiwagi’s own personal Japanese chef.
Stacks of $5,000 chips were readied and on the third day after arriving at Trump Plaza, the action commenced.
Normally one to want to avoid the limelight, Kashiwagi was the centre of attention as the media and alike watched on.
Baccarat does have the smallest house edge of all casino games, which can be as little as 1.06% on the banker bet, but Kashiwagi was doing more winning than losing.
After two days, he had secured $6 million of Trump’s money and decided that it was time to return to Tokyo before achieving a celebrity status he was uncomfortable with.
However, by the end of the year Trump had managed to tempt Kashiwagi back for a rematch. Although this time some specific rules had been included as part of the showdown.
Trump had called upon the services of Jess Marcum, a scientist, card whizz and genius when it came to mathematical analysis.
Marcum had developed his own blackjack system that had consistently proved successful in high-stakes games. He is regarded as the inventor of card counting.
Although over 70 at the time, Marcum consulted that the key was that Kashiwagi simply needed to be kept playing for longer to allow the house edge to come into effect. It was recorded that around 700 hands were played during the first visit.
Therefore, a double-or-nothing rule was created for the return game, where Kashiwagi would sit down with $12 million and keep playing until this became $24 million or he was wiped out.
Taking his seat for a second time at the Trump Plaza, Kashiwagi settled down to continue the winning streak from his previous visit months earlier.
In fact, this time he was up $9 million, which meant his total profits across the two visits stood at $15 million.
Given the size of his arrears, Trump was said to be ready to call it quits. Yet, Marcum was convinced that the mathematical probabilities would eventually swing back in Trump’s favour.
It may have been pure coincidence, but a change of dealers from all male to all female began to turn the tide. As a losing streak began to take shape, Trump was quick to ensure that the females remained too.
Marcum believed that Kashiwagi would only have around a 15% chance of doubling his $12 million if he played somewhere in the region of 5,000 hands.
The game finally ended after 5,056 hands, with The Whale down $9.4 million. This left Trump in $3.4 million profit overall.
There have been contrasting opinions as to why the game was ended prematurely and not in line with the agreed rules. Did Trump dishonour the original deal or had the pair agreed to new terms during play?
One of the reasons that this will never be cleared up is because Kashiwagi was found murdered in his Japanese home in January 1992 after being assaulted with a samurai sword.
The case remains unsolved to this day, although his underworld connections have linked the Yakuza Japanese crime syndicate to the death.
As for Trump, he never received his money. Kashiwagi was playing with credit and had flown home before his cheque from a Singapore bank had cleared.
He did get his publicity, but Trump Plaza was one of three of the president’s Atlantic City casinos to go bankrupt in 1992. It closed permanently in 2014.