Adam Kaufman

Jon Lester’s new contract will put him under the microscope more than ever

Jon Lester 8.jpg

Though the Red Sox and pitcher Jon Lester have put their contract talks on hold – or "hit the pause button," as general manager Ben Cherington said – an extension feels inevitable.

The veteran lefthander is part of the Boston fabric, twice a World Series hero and four times the club’s Opening Day starter. That’s not to say Lester couldn’t leave in free agency, of course. We’ve watched as more beloved stars have skipped town in recent years, like Pedro Martinez, Jonathan Papelbon, or Johnny Damon.

Guys move on, whether for a better opportunity, larger checks, or because they’re no longer wanted. Affordable, good-will, emotion-driven contracts are saved for exceptions like David Ortiz, and only the exceptionally loyal like Dustin Pedroia stay for less because they feel at home.

Lester has suggested he’d do the same. The pitcher has said and done all of the right things since early this winter, from claiming a desire to take a “hometown discount” to holding court with media seemingly at their beck and call, never speaking out of turn or coming off as greedy or entitled. It’s been something to behold.

But under all of the negotiating and public declarations on both sides over what is and isn’t contractually acceptable – in the vaguest of terms – Lester’s desire to stay and the Red Sox' interest in keeping him appears genuine beyond the bounds of what’s best for business on either side.

Continue Reading Below

In time, the 30-year-old southpaw and his reinvigorated bling-boasting bosses will come together and iron out a new pact for a higher average annual value than ownership would like and fewer years than Lester would prefer (in a similar vein to the Mike Napoli and Shane Victorino deals).

Something in the neighborhood of five years and about $120 million could be considered a compromise for both sides, and would allow Lester to preserve the market value for his fellow hurlers. For the sake of comparison, Zack Greinke, a very similar regular season pitcher with limited playoff success, cashed in for $147 million over six years just after his 29th birthday in 2012. Tigers Cy Young winner Max Scherzer recently turned down a six-year, $144 million extension, which Lester all but said he would have accepted if given the opportunity. Presumably, the Red Sox have not broached those terms, likely because of the length.

Lester will get his money, either during the season or next winter, and when he does he will be under the microscope like never before.

The ninth-year pro is in the process of earning a personal-best $13 million this season. Soon enough, he’ll be making close to double that total. As a result, every start will matter more. The scrutiny will be higher.

Early in his new deal, Lester will be relied upon to put up numbers similar to his career track record, where he’s won nearly two-thirds of his decisions (100-58), posted a 3.75 ERA, and demonstrated incredible health and durability (averaging 205 1/3 innings over the last six seasons).

More than that, though, he’ll have to be consistent.

Don’t look purely at a stretch of six years in which he’s made at least 31 starts, and won 15 games or better and pitched 203 innings or more on five occasions, and automatically label that “consistency.”

Consistency in its truest form is what Lester did in 2010, when the All-Star finished fourth in Cy Young voting behind runaway winner Felix Hernandez, courtesy of a 19-9 record and a 3.25 ERA. Save for a three-start blip to start that season and his final outing of the year, he enjoyed a 28-start run with a 2.49 ERA over 188 innings.

That’s consistency.

In each of Lester’s other big league campaigns dating back to his rookie year in 2006, there have been lengthy hiccups.

For six straight starts that first year, the MLB newbie showed an 8.13 ERA after allowing 28 runs over 31 innings. He deserved some slack, though, as a 22-year-old kid pitching in the bigs for the first time.

The following year, long before starting the World Series-clincher in Boston’s second championship in four seasons, Lester had a 6.26 ERA spanning five starts. In the grand scheme of things, though, he was achieving remarkable things after missing the first-half of the year to treatment for his lymphoma.

In 2008, the then 24-year-old had his first full season and he was tremendous, going 16-6 with a 3.21 ERA, but not without getting shelled in his opening six outings, with a 5.40 ERA.

The next year was filled with ups and downs. On the surface, Lester pitched well with a 3.41 ERA in 203 1/3 innings, however his first 10 starts displayed a 5-5 pitcher with a 6.07 ERA. That came in the wake of signing what’s become a six-year, $42.75 million deal.

The chicken-and-beer-faced collapse of 2011 was more of the same for the second-time All-Star. For one five-start stretch, Lester’s ERA was 6.52. In September, when the Sox went just 7-20 to fall out of playoff contention, the perceived ace was 0-4 with an 8.24 ERA over his final four starts.

Those uncomfortable bouts with failure got longer and more painful in 2012, when he allowed 63 earned runs to score over 90 innings in 15 straight outings, resulting in a 6.30 ERA. In what was a miserable season for the entire team, Lester went a career-worst 9-14 with a 4.82 ERA.

And, last year, prior to turning around his season and the perception of fans who once wondered if he should even be in the playoff rotation, Lester suffered through a dreadful six-week span in which he had a 6.27 ERA over 11 appearances. Of course, he was one of the game’s best pitchers in the second-half with a 2.57 ERA over 87 2/3 innings and into the playoffs, when he had a 1.56 ERA in five starts, and the rest is history. As such, the future will be expensive.

Only in 2010 were those hiccups limited to a start or two, and Lester will be tasked with finding that same good fortune again the moment he inks his new, lucrative deal. He’s human, but he’ll be paid among the elite and will be forced at least at the start to pitch like it.

So far in 2014, Lester’s been just fine. After a 0.71 ERA in three spring starts, he has given up four earned runs over 14 1/3 innings for a 2.51 ERA. His teammates’ lack of offensive and defensive support have held him winless.

Is it fair to look at previous seasons and question the dollars involved in retaining Lester for years to come? Certainly. It’s also tempting at times to look beyond the veteran to the promising prospects who anxiously await their turns, but the lefty is the cornerstone in a rotation filled with future uncertainties. Lester is the closest thing the organization has to an ace. Since the start of the 2008 season, he’s tied for third in the American League with the Angels’ Jered Weaver with 89 wins.

At some point, Boston will have to spend big dollars for top talent again. A relative short-term deal – compared to what Lester could command on the open market – with one of its own, and someone who also happens to be a playoff-tested and stable commodity is a sound investment.

Once negotiations are un-paused and a deal is reached, Lester’s consistency will matter most. In many ways, it already does.

Follow me on Twitter at @AdamMKaufman

More from this blog on: Red Sox