Bruce S. Bennett

Bennett has counseled Orange County and Detroit through bankruptcy, but now he's moved onto something even bigger: Puerto Rico.

"Puerto Rico is different than a county or a city, it's a commonwealth, which has its own legal complexities and, in addition, Puerto Rico has a lot of units of government underneath it," he said.

Bennett, who specializes in business reorganization and municipal debt restructuring, is lead counsel for several instrumentalities such as the Puerto Rico Aqueduct and Sewer Authority and the Puerto Rico Electric Power Authority.

The U.S. territory has been coping with a $70 billion debt. This summer, the federal government enacted the Puerto Rico Oversight, Management and Economic Stability Act, or PROMESA, which creates an oversight board with budgetary and fiscal control over the Caribbean island.

While Chapter 9 of the U.S. bankruptcy code is not applicable to Puerto Rico, parts of PROMESA are modeled after it to help move forward with restructuring, Bennett said.

"We're now in the transition from the pre-PROMESA world where nothing was defined...and now we're operating a new statute that in some respect borrows heavily from a statute that's very well understood at this point," he said.

As co-lead counsel in Detroit's Chapter 9 case, Bennett helped it eliminate nearly $8 billion of its debts, while the city could still afford to invest approximately $1.2 billion in its rehabilitation over the next decade. City of Detroit, Mich., 504 B.R. 97 (Bankr. E.D. Mich. 2013).

In Orange County's $1.7 billion loss, Bennett worked as lead debtor counsel to help recover $870 million.

Bennett has also had his hand in the sports world acting as the lead lawyer when NBA legend Earvin "Magic" Johnson and other partners acquired the Los Angeles Dodgers for $2 billion.

But for now, Puerto Rico will be among the biggest demands of his time, which he said means plenty of trips to its capital.

"More is going to be happening in San Juan than Los Angeles," Bennett said. "There's going to be nonstop flights."

— Arin Mikailian