Multiple Major League Baseball teams are looking for starting pitchers this offseason. Jon Lester and Max Scherzer are the biggest free agent pitchers still available. Recently, John Henry, owner of the Boston Red Sox, flew to Lester to speak with him about a potential deal. It remains to be seen which team he eventually signs with, but Lester is going to command a huge contract sooner rather than later. 

Most analysts have pegged four teams as vying for Lester’s services. This includes the Red Sox, New York Yankees, Los Angeles Dodgers, and Chicago Cubs. So far, he’s received deals ranging from $140 to $150 million. The lefty is expected to wind up with a $150 to $200 million contract for five or six seasons. According to most sources, he has leaned toward returning to Boston. 

Regardless, a $150 million investment in Lester sounds like a bad deal waiting to happen. A $200 million investment in the free agent would be heinous. Team revenues in baseball have been increasing by leaps and bounds, though.  I was talking about this with a friend while reading about Kenneth Griffin. Therefore, Lester’s huge payday can be attributed to a strong walk-season before free agency, plus the increase in teams’ pocketbooks. 

Chances are high that Lester’s next contract will pay off at first. He’s a high-caliber pitcher that hasn’t shown signs of decline yet. At age 30, the pitcher is nearing the age where pitchers tend to decline, though. Year four or five of this deal could start to look like a nightmarish overpay. Multiple teams have seen plenty of those deals in recent years.