Jon Lester’s Dashed Bid for 20 Wins the Last of Many Disappointments of Season

Perhaps we should’ve seen it coming.

In a season that has been filled with several shining moments for the Red Sox followed up by incredible downers, one of the last remaining pieces of drama was a painful exercise in dashed dreams.

Jon Lester, bidding to become the sixth left-hander in team history and the first since 1953 to reach 20 wins, was rocked for eight runs in four-plus innings of an 8-2 loss to the Chicago White Sox on Wednesday night.

It was a game that featured a 21-minute power outage during the sixth inning at U.S. Cellular Field, but there was no lack of power against Lester, who surrendered his first career grand slam to Paul Konerko and then a two-run shot to Dayan Viciedo, just the fifth time all year Lester has given up multiple homers.

The big lefty never had it, and an otherwise superb season will end without the milestone. Lester finishes 19-9 with a 3.25 ERA and matches his career high with 225 strikeouts. He was aware of the chance to make history, but said it had nothing to do with his lack of command.

"It’s something that is there and you can't hide from it. I don't think it had any bearing on the outcome of tonight's game. I just didn’t go out and execute pitches," Lester said. "Regardless of whether it's the 20th or first win of the year, that’s the main thing it comes down to. I didn’t execute pitches and I got myself into a lot of jams I couldn't get out of."

With the Sox officially eliminated from playoff contention a few nights ago, the remainder of the season had just a handful of anticipated events. There is the weekend series with the Yankees which offers a chance for Boston to play spoiler to New York’s pursuit of a division title. There is Clay Buchholz’s bid for the American League ERA title, which will come to a head Saturday at Fenway Park. The team’s pursuit of 90 wins might mean something to someone somewhere. "Thanks, Mike Night" will give fans a chance to honor Mike Lowell on Saturday.

But chief among the attractions in five otherwise "meaningless" games was Lester’s big outing in Chicago. He entered having won six straight starts while posting a 1.76 ERA and 54 strikeouts in just 41 innings.

It was a stretch that not only brought Lester to the brink of history on Thursday, but had thrust him into the conversation surrounding the Cy Young Award. After his win in New York on Saturday, the normally stone-faced Lester managed the smallest of smirks when asked about the possibility of taking home the honor, but that too is an impossibility after his ERA jumped an alarming 0.29 and he allowed at least seven runs for the third time in 2010.

The promise of the evening took an immediate hit when leadoff man Juan Pierre singled off Lester to being the bottom of the first. Two stolen bases by Pierre and a single by Andruw Jones gave the White Sox the first run of the game.

Pierre singled again and scored on another Jones hit to tie the game 2-2 in the third, and Lester had already thrown 53 pitches, a harbinger of a long inning to come.

Lester walked two in a 38-pitch fourth, the worst of which was a flat, 3-2 belt-high fastball that Konerko smoked for the first home run off Lester in 45 innings and the first ever off the lefty with the bases loaded.

"The fourth, a couple of walks leading up to Konerko and then he ran deep into the count," Red Sox manager Terry Francona said of the moment when it all fell apart for Lester. "Konerko’s done that to a lot of guys, got a pitch he could handle and hit it out of the ball park … it was kind of downhill from there."

Although he got the final out of the fourth, Lester surrendered a single, a home run and a walk to start the fifth. He was mercifully yanked before he could even qualify for No. 20.

Just 52 of Lester’s astonishing 99 pitches (52.5 percent) were strikes.

While one start has prevented Lester from gaining a few more accolades, he still deserves plenty for an awesome campaign. His 19 wins are second only to Josh Beckett's 20 in 2007 among all Red Sox hurlers over the last six seasons. He had at least 32 starts and 200 innings for the third straight year and finished with a career-low 1.20 WHIP.

Additionally, Lester finished 12-2 with a 2.96 ERA against divisional opponents, the kind of results any club would want every fifth day, especially in a group such as the AL East.

With the season Lester had, he deserved a better ending. But with the way 2010 has gone for the Sox, there figured to be another disappointment in the little time that remained.