JIMMY PIERSALL (RED SOX, 1950, 1952–1958) He brawled with Billy Martin. He spanked a teammate's son. He heckled umpires and fired water pistols at home plate. Soon, his erratic behavior got to be too much. And, after getting suspended and seeking treatment at Westboro State Hospital, the centerfielder was diagnosed with nervous exhaustion bipolar disorder, missing the rest of the 1952 season. Later in the '50s, his autobiography, Fear Strikes Out, was turned into a movie starring Anthony Perkins. Piersall later disavowed it, but he did have an interesting perspective on his mental travails: "Probably the best thing that ever happened to me was going nuts," he said. "Who ever heard of Jimmy Piersall, until that happened?"
DEREK SANDERSON (BRUINS, 1966–1974) Renowned for telling a reporter that his pre-game meal was "a steak and a blonde," young "Turk" was a regular Huggy Bear about town — tooling around Boston in a Rolls Royce, draped in a fur coat, and flashing bling galore. Alas, the high life went to his head, and drugs, booze, and bad investments left him broke and in bad health. But he turned it around! Despite losing millions, he eventually found employment at firms like Street Global Advisors and Howland Capital Management in Boston. (Bonus points awarded for being Derek Jeter's namesake.)BILL "SPACEMAN" LEE (RED SOX, 1969–79) Where to start? "Lee was one of the game's few counterculture symbols," reads Spaceman's induction essay to Baseball Reliquary's Shrine of the Eternals. "He talked to animals, championed environmental causes, practiced yoga, ate health foods, sprinkled marijuana on his buckwheat pancakes (an indiscretion for which he was fined $250 by Commissioner Bowie Kuhn), pondered Einstein and Vonnegut, quoted from Mao, and studied Eastern philosophers and mystics." He ran for president ('88) on the Canadian Rhinoceros Party ticket, had a song written about him by Warren Zevon, went to war with Don Zimmer and Dapper O'Neil, spoke out fiercely against Astroturf and polyester uniforms, wrote four books, and still plays on barnstorming teams. What's not to love?
DENNIS "OIL CAN" BOYD (RED SOX, 1982–1989) Supposedly nicknamed for the tins of beer he consumed copiously, East Providence's favorite adopted son was an innings eater and quote machine for the Red Sox in the '80s. The 155-pound beanpole possessed an array of off-speed junk pitches, a mercurial mood, and an inimitable way of looking at the world. "That's what they get for building a park on the ocean," he scoffed after a Sox-Indians game at Cleveland Municipal Stadium — on the shore of Lake Erie, more than 600 miles from the Atlantic — was postponed thanks to fog. A few years ago, I saw him pitch for the Brockton Rox, and he was none too shabby. Now, at age 49, the Can is aiming for a major-league comeback. Really.
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