On the surface, he led a charmed life well into his 90s, working on new characters and doing his famous cameos in over 60 Hollywood comic blockbusters.

But where he shined creatively, he lacked in money-handling, business savviness, character judgment and just plain luck.

One of the worst financial decisions Lee ever made was when he traded up his future movie points for a measly $10 million payout from Marvel; meaning, when the Spider-Man and Iron Man franchises brought in billions of dollars, not a dime went to Stan.

"Things had been weird in Stan Lee's life for a while, but in 2018, they [got] really weird," says pop culture insider Michael Pagnotta.

In 2017, his beloved wife, Joan Lee, had left him a vulnerable widower.

At the time, Lee was "hard of hearing, could "not read or drive" and was getting "easily confused." As estate lawyer Danielle Mayoras puts it, he was "ripe to be taken advantage of."

It was months before he died, and he had contracted pneumonia. A very frail Stan decided to file a lawsuit against Jerry Olivarez for fraud and elder abuse.

Mayoras recalls Olivarez going from claiming he was a florist to being a publicist and then finally assuming the position of Lee's caregiver.

The lawsuit accused Jerry of writing himself a $300,000 check and buying an $850,000 condominium using misappropriated funds.