To begin with, that estimate is Joseph Stiglitz's, not mine. He's been following this case from the beginning.
As for Singer, his TARP heist has been extensively written about. He cashed in, used his control of Delphi Automotive to ship over half its jobs to China, and left Delphi to pay the TARP loan. The Romneys, btw, were among his partners in the hesit, and made up to $115 million in the deal.
Singer, btw, is a top GOP contributor, and was even known as the vulture who hatched Narco Rubio (Rubio, of course, lobbied quite a bit on Singer's behalf).
Now then, the bonds. Keep in mind that he bought old defaulted bonds in 2008 for $48 million from resellers (not Argentina). He didn't "want his money back" or even the market value of those bonds (around $200 million); he demanded close to a billion.
Later, in fact, he added to his Argentine holdings (to $177 million) and presented those as belonging to anonymous "me too" bondholders in order to buttress his case. Argentina's new offer (courtesy of their newly-elected GOP clone) would yield him nearly $2.3 trillion, or 1180% - plus, they pay all his legal costs.
As it happens though, Singer's already cashed in by way of the CDS default insurance he took out on these same bonds. That payout was granted in August 2014 (when his pet judge, Greasa, blocked Argentina from paying its own bondholders). Those legitimate bondholders had been collecting in full and on time since 2005 - and even made a sizable profit.
To use your analogy, it's as if you paid your mortgage, only to be told that a local judge put a hold in that check, and all future checks, until you either default on your mortgage or pay some criminal you don't even know an astronomical sum. Being a smart guy, you'd realize right away that the mystery individual wants your property without paying you for it; in fact, he even took out insurance on your property. Think Boss Hogg, if you remember the Dukes of Hazzard (basset hound optional).
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