What’s the biggest check you’ve ever written? The biggest check most people will ever write is probably a few thousand dollars to cover first/last months rent and a security deposit for an apartment. Any larger amount, like a down payment on a home, is usually wired electronically.

The same goes for the business world. A business will cut checks for employee salaries and maybe some smaller business deals, but for bigger transactions an electronic wire is by far the preferred method.

On the other hand, there have surely been some very large checks written during the course of modern financial history, from the millions to the hundreds of millions of dollars. So what is the single biggest physical check ever written? To find out, we need to travel back in time a bit…

October 2008

It’s October 2008. The world is reeling from an out-of-control financial crisis. The entire global economy was in a free fall. Banks that weeks earlier were considered among the most reliable and steadfast institutions in the corporate world, were perilously close to insolvency. Lehman Brothers had just failed and Bear Stearns was acquired for pennies on the dollar.

And then there was Morgan Stanley.

By all accounts, Morgan Stanley was the next in line to go under. Desperate to prevent their demise, executives from Morgan Stanley reached out to several large foreign entities for a lifeline that would shore up the bank’s finances and show investors the bank would survive.

Morgan Stanley flirted with a state controlled Chinese bank for a time, but ultimately found a potential match with Mitsubishi UFJ.

The problem was urgency. Investor confidence had decimated Morgan Stanley’s stock price from nearly $60 a share to less than $10, and there didn’t appear to be an end to the pain in sight.

“Too bad you can’t just write a check!”

Teams from both firms held an emergency meeting over Columbus Day weekend in October 2008. After 48 straight hours of negotiations, the two sides had a deal worked out and a final price tag. Mitsubishi would invest $9 billion into Morgan Stanley in exchange for a 21% ownership stake and a 10% annual dividend.

Under any other circumstances in recent financial history, a $9 billion transaction would be made whole via an electronic wire from one bank to the other.

That’s where the negotiating teams hit a wall.

#1) First off, it was a holiday weekend and banks would be closed in both countries until Tuesday.

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#2) Secondly, wiring any amount of money usually takes 2-3 days and Morgan Stanley may not have survived another 24 hours.

#3) Third, Morgan Stanley was itching to make a formal announcement of the merger as soon as possible in order to stop their stock price from plummeting any further.

Desperate for a solution to the $9 billion problem, one of the Morgan Stanley deal makers joked “too bad you can’t just write a check!“

Both teams erupted in laughter. But then, a few minutes later, one of the top Morgan Stanley executives made the astonishing realization that a check actually might work.

If Mitsubishi had the funds to cover a $9 billion check, there was no reason why Morgan Stanley couldn’t accept and deposit it before the markets opened Tuesday morning. From an accounting/regulation standpoint, a paper check “checked” all the boxes that allowed Morgan Stanley to officially announce the merger and hopefully reverse their deteriorating stock price.

The Japanese team quickly left to call the home office and research their capabilities. As luck would have it, Mitsubishi UFJ did indeed keep enough of a checking account balance to cover and clear a $9 billion check.

After a few hours of phone calls and arrangements, the Mitsubishi bankers returned to Morgan Stanley’s headquarters with a check for $9 billion. That’s the number nine followed by nine zeros. Eleven zeroes if you count the pennies. It was, and still is, the biggest check ever written.

Here’s a photo of the actual check:

Morgan Stanley immediately announced to the world that they had a done deal.

On Tuesday, their stock surged 85% from $9.68 to $17.92. Today Morgan Stanley’s share price is above $100. The company’s market cap is $190 billion. So that $9 billion investment for a 21% stake has turned into $40 billion not including dividends!

All thanks to a paper check.

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