It's hard to imagine anyone in the world who's got a better gig than Tim Wakefield. Today, the Red Sox are expected to pick up his perennial option, just like they have every season since 2005, and bring him back in 2009 for this 15th year as a Red Sox pitcher and his 17th year in the big leagues (he pitched for the Pirates in 1992 and 1993).
As his contract is structured, the Red Sox give him an MRI and a physical at the end of every season, then decide whether or not they want him back for $4 million. And who wouldn't want a guy that can make 30 starts with an above average ERA back at that price? Wakefield got rocked by the Rays in the playoffs, but he hasn't had an ERA+ of below 100 since 2000 and he's only thrown less than 150 innings once in that span.
As for Wakefield, well, 20 years ago he was a first baseman, coming off a year in which he hit .189/.326/.306. With the Sox exercising this option, he's made almost $50 million as a knuckle-baller, he's got a World Series ring, no pitcher in history has pitched more consecutive seasons for the Boston Red Sox, and he'll likely get his 2000th strikeout next season. Not a bad run for a guy that nearly whiffed his way out of a career in baseball before it even started.