An alumnus of Drexel Burnham Lambert and Apollo Management, Antony Ressler, the cofounder of private credit giant Ares Management, has spent decades building one of Wall Street’s most durable money machines. Now 64, he was an early and aggressive backer of non-bank direct lending, helping scale his firm into a $600 billion giant by lending to middle-market companies that were often neglected by traditional banks. The surge in assets—and the steady fee streams and dividends that came with it—propelled Ressler onto the Forbes 400 list of billionaire Americans in 2015 and financed a growing portfolio of assets, including the NBA’s Atlanta Hawks.

Doug Ostrover and Marc Lipschultz rode a similar wave. The cofounders of Blue Owl built one of the fastest-growing firms in alternative assets by combining a scaled private credit platform with a booming secondaries business (buying stakes in other buyout firms), created through the merger of Owl Rock and Dyal Capital in 2021. The result: a $300 billion-plus firm whose rapid growth minted multibillion-dollar fortunes for its top executives, who purchased luxury real estate and stakes in sports teams.

These days, Ressler and the Blue Owl guys find themselves in an unfamiliar position—losing money rather than gaining it. Ressler’s net worth declined $3.3 billion between September........

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