Larry Silverstein's Controversial Business Decisions

Larry Silverstein has got to be both the stupidest and the luckiest

businessman of all time. As a matter of fact, he's so stupid

that he bought and

signed a 99-year lease to the World Trade Center buildings 1, 2,

4 and 5 on July 24th, 2001, during which time all

four buildings were filled with asbestos, which, as you may know, is pretty deadly

to humans and is also a bitch to clean out.

I guess you can say he was just doing as best as he can.

The reason this was so stupid was that the cost of removing all

that asbestos

would've been in the hundreds of millions, potentially up to a billion dollars,

almost the entire value of the buildings he just bought.

A poor business decision by any means.

Sort of like buying a car with 200,000 miles on it at full price.

Well, on top of that, owning the lease meant

that Larry had to buy insurance.

The insurance company valued his newly leased World Trade Center buildings at

$1.5 billion, to which Larry stupidly responded, "No,

no, no, no, no. They're not worth 1.5 billion.

They're actually valued closer to a total of $3.5

billion," which intentionally raised the insurance rate he'd have to pay for the

buildings. Like, imagine your accountant calculating your

taxes for the year and

you being like, "Mm, no, no, no, no, no. This, this is too low.

Let's try to bring that number up a bit." So he bought

insurance at a rate higher

than he was quoted on buildings that were already infested with asbestos.

But let me tell you, it sure don't end there, Johnny boy,

because six weeks after

he purchased the lease to those buildings, it was September 11th,

2001, 9/11, and two of the buildings he just insured,

WTC

1 and 2, tragically collapsed after planes crashed

into them.

A once in a lifetime event, the odds of which happening

were astronomical, and

lucky Larry just so happened to buy insurance on those two buildings a month

and a

half earlier at a rate higher than the insurance company initially quoted.

But oh, Larry's luck didn't end there because he

argued that since two

planes hit the buildings on that day, they should be counted as two separate

insured events, meaning he should get paid double his

insured value of

3.5 billion to $7 billion. But the insurance company

disagreed, so he sued them and they settled six years later in 2007

with the

insurers agreeing to pay him out $4.55 billion.

A whole billion dollars more than his original 3.5 billion insured amount,

and somehow his luck just kept on getting luckier.

You see, Larry was a bit of a workaholic who

founded and ran his own company,

Silverstein Properties, a New York real estate development firm,

whose office was

located at World Trade Center Building 7, where he would go into

the office almost every day except on the morning of September

11th, because he coincidentally had a

dermatologist appointment that very

same day. One of the only days he ever missed work

happened to be on one of the

biggest tragedies of American history, where the building that he was supposed to

work in just mysteriously collapsed to the ground without a plane even hitting it.

What a lucky guy.

End of transcript · 563 words

iPhone app Translate videos on your iPhone Paste a TikTok, Instagram or X link, add subtitles in your language and save the video to Photos.

Read any video in your language

Paste a link from X, TikTok, YouTube or Instagram. You get a page like this one.

© 2026 TranslateMom Transcripts Sources Pricing Legal