Jon Lester's $70 million contract offer

While Red Sox nation was focused on the team's doomed efforts against the Yankees, a bit of information slipped in under the radar regarding the extension talks between Jon Lester and the Red Sox. Per Ken Rosenthal of FOX Sports:

The Red Sox's most recent offer to Lester was far below market value -- four years for between $70 million and $80 million, according to sources within the team'€™s clubhouse.

To this point we'd been left to speculate which side was "to blame" for the lack of progress in the spring. Was Jon Lester being unreasonable? Or were the Red Sox being stingy? The implication from Rosenthal is that the latter is true. Indeed, $70 million seems relatively low for a pitcher of Lester's reputation. But there are two things to take into consideration...

1. This is an initial offer
2. Made to a player who specifically indicated his willingness to give the Red Sox a home team discount.

It's really no surprise to see the Red Sox coming in low, then. Maybe it could be seen as bad faith for the team to try to test just how far a player's loyalty will go when they've taken the first steps to put business aside in favor of sentiment, but it's simply the nature of clubs to always have dollars in mind. Even if, say, Ben Cherington is of the mind to play softball with him, there are plenty of individuals involved in formulating and approving any given contract offer, and that makes it a lot easier to remove personal feelings from the process than it might be for the player on the other side of the offer.

All that being said, though, $70 or $80 million over four years really shouldn't be seen as that far off from what Lester might expect. That's between $17.5 and $20 million, which would make Lester the highest paid player on the Red Sox. It would put him slightly above Anibal Sanchez per annum, and leave him well above the likes of Matt Garza.

Photo Credit: Al Bello

The go-to points of reference, however, seem to be Max Scherzer's rejected offer and Homer Bailey's extension. The former doesn't really work; Scherzer is simply on a different level, particularly if you give him credit for the peripherals that have shown a breakout was in store, if not perhaps one as dramatic as 2013 brought. Some would claim that Homer Bailey is not a fair comparison either, and that Lester is to Bailey what Scherzer is to Lester. Consider Matt Snyder of CBS' argument:

Homer Bailey of the Reds just got a six-year, $105 million contract extension. Lester is roughly three years older, sure, but here are their career numbers:

Lester: 101-58, 3.74 ERA, 118 ERA+, 1.30 WHIP, 8.1 K/9, two-time All-Star
Bailey: 49-46, 4.29 ERA, 95 ERA+, 1.33 WHIP, 7.4 K/9, zero ASG

Obviously, Bailey has been much improved in the past two seasons, but the fact remains that the track record shows Lester should be more highly compensated. Add in the fact that Boston is a much larger market than Cincinnati and Lester was just the ace of the World Series champions last season and that deal above is a head-scratcher.

It's a fair point to make if salary were a reward to be given for past performance, but it's not. Instead, it's a valuation of future performance. How much do Homer Bailey's first few years in the majors matter when it comes to predicting what he might do in 2015 and beyond? Snyder owns up that Bailey has been better over the last couple seasons, but that should be followed by a full stop rather than an appeal to 2007 and 2008.

If we look at their most recent history--what we might expect to give us a picture of who they are now--Lester and Bailey come out dead even with a 105 ERA+ over the past three years. Age aside, this really is a reasonable comparison, and the Reds and Bailey have agreed that something like $17.5 million is fair compensation for a player of his caliber.

That doesn't mean Lester has to buy into that valuation, but it does mean that treating a four-year, $70-80 million offer like a lowball insult is kind of ridiculous. No, the fact that the Red Sox are World Champions doesn't make a difference. No, their relative market size doesn't either. The Reds don't get free agents half off because they're small market, the Red Sox don't have to offer up more because they're big market. There is some merit to giving Jon Lester credit for being a strong postseason pitcher, but that doesn't push him into a different tier of pitchers. The sample size is too small, and it's not like Homer Bailey is running around with a record of failure in the postseason.

In the end, I wouldn't expect the Red Sox to go much higher than this, frankly. Five years, $90 million? Sure. Five and $100? Six and $108? Less likely. Five and $110? See you later. Jon Lester is a fine pitcher, but even in his big rebound year of 2013 he only managed an ERA+ of 110. Again, that's good, but not elite. He's also going to be 31 before he hits free agency, and there will be quite a few options available on the market in the coming year.

The Red Sox have tried throwing caution to the wind in free agency before. It didn't work out. There are times to go over-the-top. Top-tier players require top-tier commitments, and in some situations those players are truly good enough to make a seemingly ridiculous investment worthwhile. But Jon Lester is simply not that level of player. He's not irreplaceable, and the Red Sox are understandably not going to treat him like he his.