Orel Hershiser made his name in the details. In 1988, the year the Los Angeles righty pitched 59 consecutive scoreless innings and earned NL Cy Young, World Series MVP and SPORTS ILLUSTRATED Sportsman of the Year accolades while playing for the world champion Dodgers, he kept a computer file on almost every inning he played, detailing batters and outs. Sure, he threw an exceptional sinker and a superior curve, but, as Hershiser admits, "in general, people weren't intimidated by my stuff." Instead, he says, "people said I was thoughtful about the game."
Little has changed. Today the 51-year-old lives just off the 1st tee at the Red Rock Country Club in Summerlin, Nev., 20 minutes outside Las Vegas. There, in his library, he keeps shelves of how-to guides on various leisure sports, from billiards to backgammon to cribbage. But what occupies Hershiser the most is a stack of roughly 20 books and 10 DVDs on poker, the game that has consumed him for the better part of five years. His new love—or one of them, at least.
In 2005 Hershiser was on the road in Minneapolis as a pitching coach for the Texas Rangers when he met and hit it off with Dana Deaver, a 43-year-old Las Vegas education specialist who also happened to be traveling for work. "We kept in touch, and as we got more serious, I would fly [to Nevada] to visit," recalls Hershiser of the woman he is now engaged to marry. "In the off-season she would be at work all week, and I needed something to do."
To fill the time, Hershiser became a regular in the poker room at the nearby Red Rock Casino, playing $2/$5 no-limit Texas hold 'em as often as possible, up to eight hours a day, five days a week. There he resumed his workmanlike approach to mastering the details of his craft. Beyond the books and videos, he sought out poker pro Mark Gregorich (whose career winnings top $1 million), and the two exchanged secrets: Hershiser critiqued Gregorich's softball swing; Gregorich helped Hershiser with his card game.
For Hershiser it felt like old times. "You break down poker hands like you break down the sequence of a hitter," he says. "Am I on turf or grass? Do I have a one-run lead or am I down by three? Is it the third inning or the seventh inning? To learn poker, I just started plugging in new questions and answers. Where am I in the game? Am I on the button, at the small blind or the middle position? What did my opponent do last time?"
In '08 Hershiser was ready to try his hand in the big leagues. After winning a poker invitational for VIPs and baseball celebrities at the Bellagio casino in Las Vegas, he entered NBC's National Heads-Up Poker Championship at Caesars Palace. He made the quarterfinals of the nationally televised event, knocking out the '06 champ, Ted Forrest, and two top pros, Allen Cunningham and Freddy Deeb, en route to $75,000. Shortly after, Hershiser signed with PokerStars, the same online outfit that launched the career of '03 World Series of Poker winner Chris Moneymaker. With their backing, Hershiser has played the last three WSOP Main Events, the most recent of which ended on a bad Day 2 beat, after which Hershiser tossed that hand's winner an autographed baseball.
"I'm excited to get up in the morning and be challenged," says Hershiser of his new life, which also includes an analyst gig on ESPN's Sunday Night Baseball as well as business ventures on the Internet and in commercial real estate. "I love relaxing, but it gets boring after a while. I never saw myself as the guy who would retire and play golf."