If only T. Boone Pickens had listened to me

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Falling oil prices have been hammering T. Boone Pickens’ hedge funds lately. Reports the WSJ:

All in, the funds have lost around $1 billion this year, a figure that includes $270 million of personal losses. “It’s my toughest run in 10 years,” said Mr. Pickens, a former geologist who earned billions by building an oil company and investing in energy. “We missed the turn in the market, there’s nothing fun about it.”

Early in June, Pickens stopped by TIME for a visit. He recorded a nice video for the Curious Capitalist and talked to us about Yahoo and wind farms and stuff.

At the time, I was just finishing up a column about billionaire investor Richard Rainwater’s decision to get out of oil for a while because he thought slowing demand would cause the price to drop. Pickens and Rainwater used to be friends, but the relationship soured during a period in the 1990s when Rainwater was Pickens’ boss (that is, he owned Mesa Petroleum). You can read all about it in Pickens’ new book.

Anyway, I mentioned to Pickens that I’d just talked to Rainwater. “Oh, the smartest man in the world,” he sneered. Then I told him Rainwater had just sold all his oil holdings. Pickens acted profoundly unimpressed. No, he didn’t think there was any chance oil prices would drop anytime soon.

They did of course keep rising for a while longer–Rainwater didn’t get the timing perfectly right, but then he never thought he would. But now they’re below where they were in June, and Pickens is poorer than he was in June.

This is reminding me of an e-mail I got from a reader a couple weeks ago asking me to check in with Rainwater to see what he thinks now. Will do.