This OT Oil baller is going through a rough patch

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Just 2½ years ago, when a barrel of oil sold for about $100, John Schiller and his wife, Kristi, were living luxuriantly in Houston high society. Mr. Schiller, the founder and chief executive of Energy XXI Ltd., had just closed a $1.5 billion deal to buy rival EPL Oil & Gas Inc. and create the largest publicly traded oil producer in the shallow waters of the Gulf of Mexico. Mrs. Schiller, a former Playboy model, was featured in People magazine for her work with K9s4COPS, which gives trained police dogs to law enforcement. The nonprofit ran a float in California’s Rose Parade, and the Schillers waved to crowds as they stood beneath a 20-foot statue of their German shepherd, Johnny Cash.Today, the Schillers are trying to avoid going broke. What many in the oil industry hoped would be a brief season of pain after prices began plunging in 2014 has turned into an arduously long recovery with oil stuck around $50 a barrel, affecting not only the bottom lines of companies but the personal finances of once-prosperous families.

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To cover his debts, he borrowed money from vendors to the company, and an investor who became a board member, according to company securities filings. After the board learned of the loans from the Securities and Exchange Commission and its own internal investigation, it stripped Mr. Schiller of his chairman title in 2015. Energy XXI declared bankruptcy last April, and on Feb. 2, a new board ousted Mr. Schiller, just after he’d steered the company out of Chapter 11. They let Mr. Schiller retrieve his belongings from the $2,000-a-month Jaguar the company had leased for him, then called him a car ride home, according to people familiar with the matter. Mr. Schiller was on the host committee for this year’s Super Bowl, held in Houston, but he didn’t get to go to the game. Energy XXI sold its tickets.

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He carries a thick wad of $100 bills in a silver clip emblazoned with the name of his homestead, Schiller Ranch. When times were good a few years ago, he’d take one of the bills and hand it to a stranger, seeking to “brighten someone’s day,” a colleague recalled. His spending occasionally worried associates who wondered whether he could become overextended, according to two friends. Although his compensation was on the higher end for Houston executives—he was set to earn as much as $14 million from Energy XXI in 2014—Mr. Schiller was no billionaire.

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