Unless you’ve been living under a rock or just stepped out of a time machine, you know about the depressing state of the Red Sox’ negotiations with Jon Lester. It’s a weird state of affairs – Lester said he’d take a hometown discount, the Sox low-ball him with a 4-year, $70 million offer, and he unsurprisingly rejects it. “Botching” negotiations, Boston-style.

Love ya, Jon, but you're scaring me a bit here. Photo by Kelly O'Connor of sittingstill.smugmug.com

Love ya, Jon, but you’re making me kinda nervous.
Photo by Kelly O’Connor of sittingstill.smugmug.com

Recently, the Red Sox have finally said they’d be willing to break out the checkbook and offer Lester $100 million. No mention of the possible length, but one can assume it’ll be five, maybe even six years. That’s a reasonable offer to the pitcher that’s been the ace of the staff since 2008, despite a couple years of mediocrity. It’s well within expectations of a hometown-discount type of contract, and this one shouldn’t come off as an insult this time. Just have him sign the papers already, right?

Let’s take a look at the big picture here. Lester is 30 years old. He’s got two, maybe three years until his decline phase starts. Handing him $100 million to stay in Boston until he’s 35 may end up being a cautionary tale rather than an example of when excellence is rewarded. Boston’s recent history of big money deals doesn’t exactly bode well for them, as the Carl Crawford signing and Adrian Gonzalez & Josh Beckett‘s respective extensions still stand as warnings of the dangers of albatross contracts.

Then there’s the contract year effect, where players perform best right before hitting free agency. Lester’s the second-best pitcher in the league by fWAR right now. You do not want to overpay for five years of pitching that might not be anywhere close to this level of excellence.

Even with his success so far in 2014, there’s some troubling signs. Lester’s contact rate is hovering at just above 79%. While that doesn’t exactly spell disaster, it emphasizes the need for missing bats. So let’s look at his swinging strike percentage. It’s 9.5%, good for 30th in the league. However, of the 29 pitchers with a better SwStk%, the only one with a higher contact rate is Drew Hutchison, at 79.8%. And he’s 29th.

“But Brett!” you cry, “why do his contact stats even matter? He’s getting ground balls anyway, right?”

Oh, how I wish that were true.

Since 2011, Lester’s ground ball percentage has been steadily declining from 50% to it’s current mark at 42%. Where have those percentage points gone? Straight to the fly balls. His 36.8% fly ball percentage would be the highest he’s ever had in a full season, which makes it a near miracle that his HR/9 has stayed so low (0.56) despite giving up so many more flies than he ever has. Want a good example of what happens your contact percentage goes up and your FB% balloons? Try Justin Verlander‘s 2014.

Is Lester worth it with those numbers? Here’s a quick look of some of the players who have been recently rewarded with $100-million-or-more contracts and their 2014 peripherals:

Player Contract Contact% SwStk% GB% FB%
Felix Hernandez 7 years, $175 million 72.8% 12.3% 54.3% 26.1%
Zack Greinke 6 years, $147 million 76.2% 11.4% 47.9% 30.7%
Homer Bailey 6 years, $105 million 76.3% 11.3% 49.9% 28.6%
Cole Hamels 6 years, $144 million 76.1% 11.1% 48.6% 30.1%
Jon Lester TBD 79.2% 9.5% 42.0% 36.8%

I’ll admit, anyone will look bad compared to Felix Hernandez, but the numbers back up the contract. In fact, a contract like Homer Bailey’s would be a good place to start with Lester. The key here, however, is that these pitchers all have better percentages than Lester, in regards to contact and batted balls. Sure, there’s overpays – this is baseball we’re talking about here – but these guys are all very good and have proven it time and time again. Factor in age & decline and Lester might not stack up with these hurlers in the long run.

Look, I’ve heard all the reasons Lester should stay. He’s a great pitcher, and deserves to cash in on his considerable skills. The Sox have an unbelievable amount of financial flexibility coming up in the next few years – in 2016, they only have $13.2 million of guaranteed money, and arbitration costs would, at most, barely double that. The Red Sox would have a minimum payroll of only twenty-four million dollars. Boston could take the hit of a big Lester contract even if he doesn’t fully live up to it. The rotation could essentially be Lester’s $20 million AAV plus the spare change of the rookie contracts of whoever the Red Sox call up, be it Rubby De La Rosa, Allen Webster, Matt Barnes, etc. It might turn out to be the most cost efficient rotation in the majors that we’ve ever seen.

I like Lester. I really do, and I want him to stay. But maybe the $100 million contract estimates are the actual reward for Lester now. Maybe that $70 million offer was less of an insult, and more of the Red Sox seeing what will probably happen down the line. If the Red Sox end up giving in and spending big, they can take solace in the fact that there are far, far worse options than paying Jon Lester what he wants, even if it ends up not looking like a discount in the end.