Doral Financial (DRL) is in an unenviable position as it tries to shake down the Puerto Rican government for funds it desperately needs to satisfy federal regulators.

The $8.5 billion-asset company is scrambling to find ways to raise capital after Puerto Rico's Treasury Department denied Doral's claim to roughly $230 million in overpaid taxes. That decision has depleted Doral's Tier 1 capital, putting the company in violation of a 2012 consent order with the Federal Deposit Insurance Corp.

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