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MLB free agent prediction: Jon Lester

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The A's acquired Lester to take their shot in 2014. Who will take a chance on him for the next six or seven seasons?

Dilip Vishwanat

Jon Lester was supposed to be the postseason wizard that would get the A's past an elimination game for just the second time in their last 14 opportunities. He was on his way, too. Big lead, pitching well, under 100 pitches ...

When help arrived at the scene, the game was unrecognizable. Lester had given up six earned runs. He couldn't hold the most important lead of his A's career, giving up as many earned runs in one Wild Card Game as he had in seven combined games in the ALDS and World Series. The myth of Jon Lester, postseason wizard, was busted.

Except, hold on. Watch the inning again. The first batter reached on a chopper that Jed Lowrie couldn't corral. After an out, the third batter reached on a hard 50-hopper up the middle. He walked Eric Hosmer after a sequence of unhittable strikes and unfortunate balls. The bullpen took over from there and dropped the cell phone in the toilet. Lester could have done more to help the A's win in that inning. He didn't deserve to lose his postseason wizard title.

He will still get paid like a postseason wizard. Postseason wizards get paid an awful lot.

He's also excellent in the regular season, too. That's probably more important than the other stuff up there. Lester is clearly the best left-handed starter on the market, and there's a solid argument that he's the best pitcher on the market. Who will pay him, though?

The player

We aren't that far removed from dozens and dozens of "What's Wrong With Lester?" columns. This goofball blamed mechanical inconsistencies. He was probably correct, though, and Lester made the appropriate corrections. Even with the nightmare season, Lester still ranks as one of the 20 best pitchers in baseball over the past five seasons as well as the the past 10. He compares favorably to Zack Greinke, Max Scherzer and David Price over the same timeframe.

That's if you go on raw statistics like ERA, though. If you attempt to remove his defense and park from the mix, you get something like this:

FanGraphs WAR
2008: 5
2009: 6
2010: 5
2011: 4
2012: 3
2013: 4
2014: 6

In his worst season, Lester still missed enough bats to be effective (in theory). In four of those seven seasons, he was an ace's ace -- one of the top pitchers in the American League, even if the ERAs weren't exactly sexy enough to pick up Cy Young votes. The raw stats also ignore that Lester pitched in hitter's parks more often than not, with Tropicana Field the only respite in the AL East for a pitcher who isn't getting as many grounders as he used to. Not only has Lester been good, he's been better than you might think.

He will be 31, though. If you assume that he's going to get at least a six-year deal -- and he'll probably get a seven-year contract from someone -- it's fair to wonder how many above-average seasons he has left. There have been 39 lefties in baseball history with at least five above-average seasons after turning 31. Some of them are names that make sense as comps for Lester, like Al Leiter, Tom Glavine and Kenny Rogers. There are, of course, cautionary tales like Denny Neagle, C.J. Wilson and Barry Zito.

The point/counterpoint is still alive, then. Signing 31-year-old pitchers to long-term deals is a lousy risk. But if you're going to take a risk on a 31-year-old pitcher on a long-term deal, Lester is probably one of the better bets you'll find. It's much more likely for a lefty with good control to survive the velocity apocalypse that's hiding in the bushes outside every pitcher's home, and Lester's command has been improving.

There's also the postseason stuff. You know there's at least one owner who just loves that part.

The favorites

The Red Sox would love to get him back. Lester did favorite this tweet, you know:

It's a sign! Unpack the secret message! He also put his Boston house on the market. So.

No, the favorites are the Cubs, who have a bounty of hitting prospects and a paucity of pitching prospects. Here's a list of the guaranteed contracts over the next three years:

  • Edwin Jackson ($22 million through 2016)
  • Anthony Rizzo ($17 million through 2017, with more guaranteed money after)
  • Starlin Castro ($22 million through 2017, with more guaranteed money after)

That's it. They're the Mariners of this offseason. They're going to make a big move. It's just a matter of which big move wants to partner up with them.

The ideal

The Dodgers didn't want to give up Joc Pederson, Corey Seager, or Julio Urias for a third super-ace like Price or Lester. They were forced to start Clayton Kershaw on three day's rest for the second postseason in a row, and they have to be getting sick of that self-imposed limitation. They're reportedly shedding payroll, so it might be unrealistic to expect them to build they world's first $500 million trio of starters.

I'll believe the payroll limitations when the Dodgers make their first cost-cutting move, though. The unholy idea of Lester as a No. 3 starter has to appeal to at least one of the bean counters.


The Red Sox were already OK with the idea of paying Lester nine figures. He already knows the names of the people who fold his underwear and wash his uniforms, so there's definitely a chance for them. The Cubs make the most sense, and they'll push hard. Never underestimate the universe's affinity for grade-A trolling, though. Or mine.

Jon Lester, Yankees: 7 years, $140 million

The Yankees are reportedly out, of course. Just like they were trying to avoid the luxury tax before last year. Don't trust them.