Scott Boras clients don't always chase the last dollar on the open market, as evidenced by reliever Ryan Madson's three-year, $12MM extension signed in January of 2009. Madson was entering his walk year after turning in 82 2/3 innings of 3.05 ball for the Phillies in 2008, and Boras was reportedly in favor of Madson taking the deal to provide security for his family.
Madson remains one of the best set-up men in the game, posting perhaps the best numbers of his career in 2010 despite missing time for a broken toe suffered after kicking a chair. He'll earn $4.5MM plus incentives in the final year of his contract. At 31 years old in August, you'd expect a Scott Downs-type offer being required just to start the conversation with Boras about Madson.
Madson has a couple of goals, according to Matt Gelb of the Philadelphia Inquirer: he wants to finish his career with the Phillies, and he'd like an opportunity to close. Gelb believes there is probably room in the Phillies' payroll for Madson and Brad Lidge, but not both, after this season. Regarding Madson's career success rate of 45% in converting save opportunities, GM Ruben Amaro said, "He hasn't proven it yet. We think he has the stuff to do it."
The Phillies have not been shy about taking care of business ahead of time, so perhaps Madson is a candidate for a $6MM a year extension along the lines of Matt Thornton. Thornton, however, is four years older than Madson, so there's a case for the latter to get at least three guaranteed years.