With the advent of electronic payments, what has been the biggest bank check ever written, be it personal or business? Writing bank checks had been the most popular way of non-cash payment method in the world for most of the 20th century. In business transactions, especially with mergers and acquisitions, no one paid cash if they involved a huge amount of money. Checks had been the focal point of every transaction as they provided an easier process with fewer risks while their money was theoretically safely tucked up in bank vaults. Regular folks benefited as well when dealing with personal payments. Digitally, the transfer of a large amount of money with numerous zeroes didn’t seem to be so monumental, but when it came in the form of a check, it gave a certain thrill that a small piece of paper would hold such significance.

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Meaning of Check

According to Britannica, a check referred to a ‘bill of exchange drawn on a bank and payable on demand.’ In American English it’s spelled as ‘check’, whereas in British English as ‘cheque.’ In documents, editors would amend the word depending on the intended audience. A check is written by a depositor of a bank, also referred to as the drawer or maker, and is an instruction to pay a certain amount of money to a third party, called the payee, when the check is deposited to that particular bank, or more unusually the amount drawn.

A little history of how people started using checks

Before going through the list of people writing the biggest checks on record, it would be apt to go back to the annals of history on when and how the process of using payment slips started. There’s no clear evidence on the first person who used them, so it’s still up for debate on when the first appearance of checks happened. Here are some of the interesting events in the evolution of checks:

The early years

Back in the days of the Roman Empire, they had bank-like institutions called Argentarii. There was no recorded evidence that they ever used a check as a form of payment. Some said that checks were found to have been in use in the first millennium by people from the eastern Mediterranean. The Europeans back then were late in discovering the use of this banking system, and it was only during the Crusades that they were exposed to it, as they often dealt with Muslim territories. They only adapted and experimented with the banking system in the 13th century when some of their financial pioneers established simple banks in cities such as Venice, Florence, Barcelona and Genoa. It mostly served local merchants with their transactions with one another, especially since coins were quite heavy back then, and they couldn’t protect them at home. Initially, both the payer and payee along with two witnesses would be in the bank during the transaction, to avoid fraud.

The use of the bill of exchange

The predecessor of the check was the ‘bill of exchange’ and this came about when people wanted to transfer funds from one city to another. The medieval banks only served within their home city. It was said that the first bill of exchange was inspired by documents that were used in the Muslim areas, which they called Suftadja. The difference between these bills and the modern checks was in what was written on the document. These bills weren’t used locally and they could be written from one city to be paid in another. They weren’t payable on demand and the instruction to pay was more directed to a merchant not to a bank. The bill of exchange was more like an order to pay, rather than getting paid from a bank account.

Checks started circulating in Europe and the U.S.

In the 15th century, checks went into circulation in Europe, specifically in Amsterdam, the trading center back then. However, this system encountered a snag, as fraud became prevalent and resulted in some countries banning the use of checks. Nevertheless, it continued and persevered due to the convenience it offered. The first printed versions of a check appeared in 1762, by British banker Lawrence Childs. It made things easier for the bankers to record and validate them, as they included serial numbers. Nearing the end of the 17th century, the US started to explore the issuance of checks.

The use of computers in reading checks

As it became popular, the banks couldn’t keep up with the volume of transactions that came their way, and needed several messengers to run around the city going from one bank to another carrying gold and clearing the checks. When the system became too much to handle, a clearinghouse was established so that one center handled everything. There was a time when close to 70 million checks were processed each day and that was one of the reasons why computers were introduced to the banking system, along with the use of Magnetic Ink Character Recognition or MICR. These were responsible for the characters printed on the bottom of each check, as details about the check could be read by the machine. By the mid-‘90s, close to 50 billion checks were written.

The biggest check ever written in history

The popularity of using a check as a non-cash payment declined over the years. It was quite unthinkable that this system would be overturned by electronic devices; imagine that in 2000, it was reported that the banking system handled more than 40 billion check transactions, but by 2012, it had dwindled to 20 billion. In 2023, there was a survey about it, and about 45% asked  said that they hadn’t written a check for over a year. More people today clearly preferred everything digitalized. To pay tribute to the once-in-demand form of cashless payments, here’s the biggest check ever written and the story behind it:

The financial crisis that hit America in 2008

The doomsday scenario in 2008 was perfectly described in Adam Ross Sorkin’s book entitled “Too Big To Fail.” ‘We need to prepare right now for Lehman Brothers filing and for Merrill Lynch filing and for AIG filing and for Morgan Stanley filing,’ even adding, ‘potentially for Goldman Sachs filing.’ This was said during a phone conference with his staff by Jamie Dimon, CEO of the third largest bank at that time, JP Morgan Chase. When it started to unravel, many believed that Washington wouldn’t save any of them, especially since they were investment banks and because the government didn’t usually interfere with them. However, to avoid the total collapse of these iconic financial institutions, Washington and Wall Street worked together to somehow save whatever they could from the economic free fall.

The global financial crisis opened options for banks overseas

As everyone scrambled to make a deal with the biggest banks in other countries, executives at Morgan Stanley flirted with the idea of dealing with China Investment Corporation (CIC) as they thought it was their only remaining prospect. However, the president of their security business in Tokyo called up, and said that the biggest bank in Japan, Mitsubishi UFJ, was interested in investing in Morgan Stanley. Initially, they were skeptical about it as most Japanese businessmen were known to have a reputation for being bureaucratic and were averse to taking risks. It also surprised them since the chairman of Mitsubishi reportedly announced earlier that he wasn’t investing in American banks after what happened to Lehman Brothers. However, the offer was real, and it meant that the Japanese bank was interested. Meanwhile, Morgan Stanley was flabbergasted with what the Chinese offered them, and it was clear that they were taking advantage of the situation. It could save them but at a huge cost, and they were giving up so much with what CIC offered. Since they already worked with the Japanese bank in the past, they put their trust in them.

The Morgan Stanley-Mitsubishi UFJ deal resulted in the biggest check ever written

The letter of intent was already given to Morgan Stanley with the offer of $9 billion that Mitsubishi promised. It was for the $7.8 billion convertible preferred stock along with a 10% dividend and $1.2 billion in exchange for the nonconvertible preferred stock with the same 10% dividend. However, Monday was Columbus Day, a holiday, which meant that banks were closed so a normal wire wouldn’t be made possible. The value of Morgan Stanley shares continued going down, so they needed the deal to push through as soon as possible before someone changed their mind.

The conversation in the room was ‘How the fuck are we going to get this thing done?’ and the reply was ‘They could write us a check.’ The problem was that no one had ever heard of anyone writing a check for $9 billion at that time and it wasn’t something that could be done immediately. However, they were optimistic that anything was possible, since the financial crisis ruined many careers and businesses that were thought could never happen in the biggest financial institutions in the world. The Japanese representative told them to wait and that he would see if Mitsubishi could arrange it; he called back after a few hours and said it could be done.

On the day that the check was to be given, Morgan Stanley’s CEO, John Mack was summoned to Washington, and so it was left to Vice Chairman Robert Kindler to fetch the check. He thought that it would be just a lowly executive who was instructed to give him the check, and was so embarrassed when he learned that he was about to meet with the senior executives of Mitsubishi. Those men were dressed impeccably in expensive black business suits as they handed him the $9 billion check. He walked into the office in his beach bum beige pants trying his best to look like a statesman and told them ‘This is an honor and a great sign of your faith and confidence in America and Morgan Stanley.’ Everyone snapped photos of the check, as they all recognized the rarity of it. When the Japanese left the room, Robert sent a message to John through his Blackberry and told him that he’d closed the deal, and had a $9 billion check in his hand.

Biggest personal check ever written

Having many zeroes in a corporate check wasn’t that surprising anymore, as happened with the Morgan Stanley and Mitsubishi deal, but having them in a personal check seemed to be preposterous, but that was exactly what happened in a divorce settlement involving some of the richest people on earth.

Harold Hamm and Ann Hamm belonged to society’s upper class, since he was worth $18 billion, and an oil tycoon who founded Continental Resources. In 2012, he was included in the “World’s 100 Most Influential People” listed by Time magazine. He was a self-made man, a high school graduate who worked at a gas station to help the family financially.  He took out a loan and struck it rich when he drilled in the right places.

Harold married his second wife, Sue Ann Arnall, a lawyer and economist who worked as one of the executives in his company. After 25 years of marriage and two children, they called it quits, and Sue filed for divorce. At the start of the divorce proceedings, they were quite private and didn’t attract too much attention from the media, but it was a bitter divorce as Ann presented pieces of evidence of his cheating. The judge decided that Ann should be paid almost $1 billion as a divorce settlement, so in 2015, Harold wrote Ann a personal check for $975 million as ordered by the court, and that made the headlines; at that time, they called it the biggest personal check ever written. Her first reaction was to reject it, and said that she would be appealing the decision as it was a minuscule amount compared to her ex-husband’s net worth, but for some reason, changed her mind and deposited it in the bank. Some people said that the reason behind it was the reports that came out at that time had indicated an abrupt decrease in the price of her ex-husband’s stocks, and that had an effect on his net worth. During an interview with CNBC, he said, ‘That became a famous check. But it got the job done.’

Some of the most interesting checks written in history

Most of the checks that were written were simply made to pay for something bought or services rendered. However, there were instances in which the stories behind those checks were more interesting than the others.

A $100,000 check in the late 1960s, valued now at over $1 billion

In 1967, Kansas City Athletics, a major league baseball team, transferred to Oakland and left the city of Kansas without a professional baseball team. A Missouri senator back then, Stuart Symington, was so annoyed at this development that he threatened to file legislation that would remove any antitrust exemption on baseball, unless the city was given a team again. The city was awarded one of the four teams that would be included in the sport’s expansion program, but needed to wait three years to execute it. The senator wasn’t pleased about it and pressured Major League Baseball to include new teams in the next season, which they did. The Kansas City Royals was formed along with Seattle Pilots, and the check that was paid for it was worth $100,000. In 2023, Forbes estimated the value of the team to be a little over $1 billion, with an operating income of close to $33 million.

Guinness Book of World Record’s  largest value paid by a single check

Before the Morgan Stanley check happened, the one who held the Guinness World Record of having the greatest amount paid by a single check was Nicholas Morris. Back in 1995, he was the Company Secretary of Glaxo, a global biopharma company – he signed the check amounting to $4 billion as payment by his company to Wellcome Trust Nominees Limited shares. At that time, the Lloyds Bank Registrars’ computer system couldn’t print out the amount on the check, and so it was one of Lloyds’ employees who manually did it using a typewriter. It took the employee three times before she produced the check properly with reference number 020503, as she was completely overwhelmed with the staggering amount, and the fear of making a mistake.

The Morgan Stanley and Mitsubishi UFG tie-up wouldn’t have been possible if there was no trust between the two financial institutions. The former MUFG CEO, Nobuyuki Hirano, said that when the crisis in Wall Street started, they were in the loop on tie-up talks with Merrill Lynch and other investment banks. However, they disregarded all of it because none of those investment banks had a structure that fitted into their strategy and corporate culture, except for Morgan Stanley. The myth that went around back then was that they did it within 24 hours but it wasn’t true. He said, ‘Actually, we spent three days, 72 hours. But it was still too short a time to decide on a huge, $9 billion investment.’

With most business transactions these days being done electronically, it would take another financial emergency or monumental crisis for something to top the biggest check ever written in 2008.

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