I will be the first to admit that baseball contracts, especially in the last ten years, are absurd. There is no doubt in the world MLB players are some of the greatest athletes in the world, and if you are the best at what you do, you deserve to be compensated for it. But unlike other sports, MLB contracts are completely guaranteed. Once you sign your name on that dotted line, all of that cash is now yours, no matter how you perform.

Despite how we may feel about the amount of money baseball players make, it’s fair market compensation for what teams are generating in revenue. TV deals are through the roof, which has allowed free agents to demand more money simply because the owners have it. Even average position players like Shin-Soo Choo can make $130 million.

The Red Sox are at a serious crossroads when it comes to ace pitcher Jon Lester. We’ve yet to crack June, yet the clock is ticking ever so slowly towards Lester becoming a free agent, where he can test the waters of other teams. Believe me, there will be plenty of suitors waiting to write him a hefty check.

Lester has always been a special player in Boston. Early in his career he was diagnosed with Non-Hodgkin lymphona, a form of cancer. He battled back, making a triumphant return to the mound in 2007 where he won the Series-clinching Game Four of the World Series. It was his first ever post-season start. The following year he threw a no-hitter, solidifying his spot in the hearts of Red Sox nation.

So far he’s played a key role in two World Championships for the Red Sox. With a mere 2.11 ERA, he’s become one of the best postseason pitchers in Red Sox history. In the regular season, he’s been a rock of consistency, never starting less than 31 games since 2008 with a record of 104-61.

The guy has just been lights out this season, by far his best of his career. Of course, it’s a contract year. Before his Thursday night start against the Blue Jays, Lester is on pace to post career bests in ERA (2.67), strikeouts per nine innings (10.83), on base percentage (.278), OPS (.626), and strikeout-to-walk ratio (4.56!!). Major statistical categories that light up the eyes of General Managers looking for an ace in their rotation. As we pointed out in the last post, pay no attention to his 4-5 record; the run support Boston has given him is putrid.

With each start, Lester is closer to free agency. With each start, he makes the case for an even bigger pay day.

During Spring Training the Red Sox offered Lester a four-year, $70 million contract extension with the hopes of going into the season not having to deal with a negotiation hanging over their heads. Nobody is laughing off $70 million, but in today’s market of lucrative deals, especially for starting pitchers, that was certainly a comical proposition.

The best we can do is put Lester’s worth into perspective compared to other contracts recently signed in the sport. After all, that’s how agents and GMs argue free agent deals to begin with. Dodgers young ace Clayton Kershaw just signed a $215 before the season, which set the top of the market. Obviously a 30-year-old Lester will command nothing close to that, but certainly more than $70 million.

A comparable offer would be someone along the lines of a Matt Cain, who signed a five-year, $112.5 million extension with the Giants this spring. Cain’s ERA may be slightly lower, but remember he is playing in the NL with no DH, and in a division that for years wasn’t very good. However, if you take a look at the rest of their career averages across the board, they are nearly exact.

Something along the lines of a five-year $115 million contract is what Lester can expect to be offered by Boston, should they counter. There is something to be said for paying a guy not only for the level at which you expect him to perform, but for what he has meant to the ball club for nearly a decade.

Lester has indicated that he wants to stay in Boston, but money talks. If the Red Sox have another offer they plan to propose to him, what are they waiting for? There will come a point where it becomes too late in the season, and Lester decides he wants to test the free agent market. If he does, he will most likely be the best starting pitcher available along with Detroit’s Max Scherzer, who rejected a $144 million extension in the spring. The chances Boston retains Lester for a similar price he may sign for right now is nearly zero.

Paying a lot now hurts. Paying even more later hurts worse. What hurts the most is watching the guy you wish you kept throw on a uniform for another team.