Annie Leibowitz

You're right, Craig. My answer was snippy and I don't assume to know what her financial decisions were. But the NYT article (as cited by wikipedia) notes the following:

They cite a "long history of less than careful financial dealings," and "a recent series of personal issues."
Not much you could do about the latter. A whole lot you could do about the former whether it be learned in business class or no.

Then again, maybe I'll just presume she's just a brilliant artist with no common sense. Those are a dime a dozen, unfortunately. Taking out loans you cannot possibly pay back and putting your residence(s) up as collateral on loans they can't secure... good move there, regardless of the 'why' or whether or not she's been successful for 40 years.
 
It's tough to determine how things went down.

First off her contract with Vanity Fair is worth millions. Plus throw in Profoto and Leaf endorsements... Plus who knows what she can do on the commercial end.

The gang at NPR seems to think bad real estate deals are to blame. For instance:

Financial Negatives: Will Leibovitz Lose Photo Rights? : NPR

"Salkin says it's unclear how exactly Leibovitz ran up her expenses. "What we do know is that she was running a studio in New York City that it seemed like the expenses got out of control. She then sold that studio and she bought three townhouses in Greenwich Village," he says.

Leibovitz started out with two townhouses, Salkin says, but when an expensive renovation caused a neighboring townhouse to become structurally unsound and she was sued, she bought that one, too.

"At the same time as all this was happening," he notes, "she had a lot of tumult in her personal life. She added two children to her family; her longtime partner, Susan Sontag, who's a writer, died; her mother and her father also died — all this in the last five years."

Nothing is ever easy.

Love & Bass
 
The loss of rights to photos past is less significant than it would appear at first glance. Consider, if you will, the senior staff at Vogue sitting around determining which of her past covers should be used for one of the up-coming issues.

She may lose two of her townhouses. Bankruptcy will preserve the third one. You need only one to live in. Any existing studio would probably jump at the chance to provide her with space with a reasonable lease.

And, of course, her marque remains just what it was: arguably the best fashion photographer in the business.

It is the lender who may end up with a loss.
 
The news articles say she also gave up rights to photo's, future.

Should she lose her copyrights, her heirs will not have financial benefit from any of her photographic legacy, her most valuable asset IMO.
 

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