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Insurance/RM nerds were amazed at the gall of this argument but for very nerdy insurance reasons, not the reasons you think. Pretty much a universally and specifically a liability policy program will define an occurrence not just as a single event (i.e. it occurred that plane one struck tower one, then it occurred that plane two struck tower two), but clearly state words along the lines of "continuous" "same basic circumstances" etc...etc... like I have a security/bouncer guy who beat the shit out of two of his co-workers but the beatings are one occurrence as they happened in rapid succession on the same day (Guy 2 tried to intervene in the first beating, and then got beat).

That said, the "face value" (bad term in this context, more of a life insurance term than a property/casualty term) of the policies on the buildings is not necessarily the value of the buildings, as they also had liability insurance for potential lawsuits for all the buildings. So it was not that Silverstein was trying to say all these buildings are worth $7B and since two occurrences happened you should pay me twice the value of my buildings (there are other clauses in property insurance that will prevent that from happening even if you intentionally overstate the value of your property by 200%). but instead was basically saying the amount of money available to him to fend off lawsuits should be twice what it was because likely the policy had an annual aggregate limit in addition to the "per occurrence" limit.

It's been awhile as this settled six years ago or so, this was regarding the property (Silverstein leased the buildings and was responsible for the insurance, though the Port Authority of NY/NJ remained the owner of the buildings, Silverstein was their tenant and made his money off subleasing to the businesses there), which was valued at 3-4.5B, but was insured for $3.5B - only if he rebuilt essentially the same buildings for the same purpose, which he originally intended to do.

He insured it through a stacked property policy program with several insurers, each of whom offered slightly different terms and most controversially, most of whom hadn't actually issued the full policies to him at the time of the incident. The judge determined that several of the policies would allow for two occurrences to be construed out of 9/11 but most would not. Silverstein claimed the extra money was to build up a new WTC to modern standards (which some insurers allow for - a coverage called ordinance or law/increased cost of construction).

The Judge ultimately split up the various claims, determining that Silverstein did not have the aforementioned coverage under any of the policies, that some policies did have to pay on the two occurrence basis, and some had to pay on one. Once these rulings were made, Eliot Spitzer took a break from banging call girls to step in and broker the $4.5B settlement between the insurers and Silverstein.

Silverstein had a legitimate reason to go for the $7B insofar as he had a business income loss (part of your property limits when you are a business include 12-24 months of income you didn't realize because of a loss). So he wasn't seeking the $7B to pay for the $4.5 maximum physical loss, he was seeking to file two claims to spread that loss so he could also recover his lost income (rents) under each claim.

It's important to realize that no matter how many occurrences or what the replacement value of the buildings were, he didn't replace them, because ultimately the Port Authority vetoed rebuilding the towers as they were, and so received a lesser settlement with the insurers. But he didn't actually receive it because the payments are tied up in the property anyway, as tenant he paid for the building's insurance, so he couldn't walk away with the money, he was basically seeking to recover on behalf of his financial interest as tenant in the property owned by the Port Authority (taxpayers) as landlord/owner.

All the proceeds are being sunk into redeveloping the area either by Silverstein or the Port Authority or both working together. He does use some of the proceeds to pay the $10M rent for the property to the Port Authority per the terms of his 99 year lease.