As weeks passed and Barbossa began to realize that either no one in Fandom had noticed he was gone or no one was coming to find him, he shrugged off any lingering feelings of hurt and began to amass himself some real treasure.
A pirate without a treasure was hardly a pirate at all, naturally, and in the short time left to him before Prohibition was repealed, Barbossa managed to expand his little speakeasy empire from the Happy Squirrel to a chain of slightly sketchy but lucrative businesses: The Drunken Squirrel, the Nosy Squirrel, and the Teal Deer (which he never explained).
It also caught the attention of the people who'd been pretty interested in cornering the market on slightly sketchy but lucrative business: the Mafia.
A few tense moments and a ridiculously blatant lie (he had no idea if the name Barbossa was Italian), and he found himself having to cut the Corleones in on a share of his profits. It wasn't Barbossa's idea of a great arrangement, but it beat the alternative of being dead. Soon he was eating pasta and cannolis and teaching the more timid denizens of New York to fear the phrase, "jes' pay the pirate 'n no one be gettin' hurt, capice?"
There were the typical dangers of life in the mob--backstabbing, shootouts, snitches who needed to walk the plank (a dramatic punishment Barbossa brought back into fashion), and the FBI trying to get him to turn on the family, an offer he finally accepted. He had no love for governments, but his affinity for mutiny had never left him.
Other than a quick stop at the Isle de Muerta for a piece of Aztec gold when he was approaching his late seventies (being undead had been no picnic, but walking the earth was a habit he'd found hard to give up), Barbossa (now living under the assumed name of Barney Stinson, something that amused only him) ran a successful casino in Monaco, which helped pay for the alimony for his series of beautiful Asian ex-wives.
All of them had talked too much.
But he was rich (very rich, just ask him), and if he occasionally terrorized the local radio djs with his esoteric musical requests, well, an old man has to have hobbies.
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The Moth -
Aimee Mann