Second-half pitching questions for Sox

The All-Star break isn't just an opportunity to celebrate the achievements of the first half. It also provides a chance to step back and examine what's to come. Let's take a look at three key questions facing the Boston Red Sox's pitching staff in the second half.

1. Will Jon Lester win the Cy Young?
In 2009, Lester carried a 4-5 record and a 5.65 ERA into June. From that point on, he went 11-3 with a 2.35 ERA -- numbers bettered only by Felix Hernandez in the American League. But those first two months doomed any chance Lester had at postseason honors and he didn't receive any Cy Young votes.

The beginning of this season was eerily similar. After three starts, Lester stood at 0-2 with an 8.44 ERA. But rather than in June, his season started to turn around in April. Lester won eight straight decisions on his way to posting an 11-1 record with a 1.90 ERA over his past 15 starts.

Lester's success stems from increasing his groundball rate while maintaining his status as one of the top strikeout pitchers in the game. His 64.0 groundball percentage is a career-high and up from 60.4 percent last season. However, while some pitchers -- like Clay Buchholz and the Atlanta Braves' Tim Hudson -- induce more grounders at the expense of strikeouts, Lester's 9.3 strikeouts per nine innings is still fourth in the AL. Combined with a vastly improved infield defense, the result is a .203 opponent batting average that leads all AL starters.

So just how impressive is Lester's combination of groundballs and strikeouts? According to STATS LLC, the last AL pitcher to equal or better both Lester's current groundball rate and strikeout rate in 30 or more starts was Roger Clemens in 1998. He won the Cy Young in a unanimous vote.

At his current pace, Lester would finish with 20 wins and 225 strikeouts. Over the last 35 years, only four left-handed pitchers have done that while posting an ERA under 3.00: Ron Guidry (1978), Steve Carlton (1980), Randy Johnson (1997, 2001, 2002), and Johan Santana (2004). Of those, only Randy Johnson's 1997 campaign did not bring home the Cy Young.

Of course, with 74 games still remaining, Lester still has a long way to go. However, this is where history is on his side.

Over the past two years, Lester has proven to be an excellent second-half pitcher, going 16-5 with a 2.95 ERA. In fact, at 23-7, Lester's .767 win percentage after the All-Star break is the highest of any pitcher whose career began in the last 50 years (min. 30 decisions).

It may not be the statistic that is most reflective of a pitcher's effectiveness, but there's little doubt that wins ultimately translate to votes.

Bruce Hurst's 1988 campaign, when he finished fifth in the voting, marks the only time a Red Sox lefty has garnered a Cy Young vote. Lester might just take home the grand prize.

2. Can the Red Sox solve their lefty problem?
With a right-handed hitter in the batter's box, the Red Sox have arguably the best pitching staff in baseball. Righties are hitting just .236 against the Red Sox, lowest in the majors. Their .699 OPS is seventh-lowest.

That serves the Red Sox well in the approximately 60 percent of plate appearances that take place from the right side. The problem occurs in that other 40 percent.

Left-handed hitters have posted a .272 batting average and a .746 OPS against the Red Sox, who rank 23rd in the majors in both categories. That last time Boston allowed a higher on-base percentage to lefties was in 1997 (.369).

As a result, opposing teams are stacking their lineups on that side, especially because left-handed hitters have crushed John Lackey, Josh Beckett and Tim Wakefield. In fact, no team has faced more left-handed hitters than the 1,602 who have stepped into the batter's box against Boston.

This problem is exacerbated by the absence of effective southpaws in the Red Sox bullpen.

Against the lefty trio of Hideki Okajima, Dustin Richardson and Scott Schoeneweis, left-handed hitters posted a combined .348 batting average in the first half. That's the highest for any AL team's left-handed relievers. Keep in mind that the league average for a lefty batter going against a lefty pitcher is just .240. Both the Yankees and Rays are holding left-handed opponents under .200 with their southpaw relievers.

With 10 walks in 13 innings, Schoeneweis' Red Sox tenure didn't last beyond May. Meanwhile, Richardson's 3.38 ERA hides the fact that lefties have a .417 BA and 1.333 OPS against him. In fact, he's allowed more home runs to lefties (two) than the entire Rangers bullpen (one).

But the true concern is Okajima. In 2009, he maintained dominance over lefties (.467 OPS) despite a significant drop-off against righties (.906 OPS). This season, his struggles have extended to lefties, who are hitting .333 with an .891 OPS against Okajima. He's already matched his career-high of seven walks to left-handed hitters, while fanning only nine.

Certainly, a team doesn't need a lefty to get a lefty out. Daniel Bard has held them to a .326 OPS, which ranks second in the majors. However, he's already shouldering the load in the eighth, an inning where opponents are hitting .156 with Bard on the hill and .310 with everyone else.

With the rotation and offense soon to get reinforcements from players returning from injury, a left-handed reliever is the Red Sox's most pressing need with two and half weeks until the trade deadline.

3. What becomes of the starting rotation?
If the disappointing 2006 season taught the Red Sox any lesson, it was that a team can never have too much pitching. In March, Bronson Arroyo was shipped to Cincinnati for Wily Mo Pena, having lost his spot in the rotation after the acquisition of Beckett.

But David Wells and Matt Clement would combine for only 20 starts. In their stead, Kyle Snyder, Jason Johnson, Lenny DiNardo and Kevin Jarvis were among those shuffled through the rotation, combining for 25 starts that could have gone Arroyo's way.

The 2010 Red Sox appeared to have a similar glut of starters, with Tim Wakefield expected to be the odd man out. Yet, between injuries to Daisuke Matsuzaka and Beckett, Wakefield goes into the second half ranked third on the team with 100 innings pitched.

Wakefield's rotation spot is again in jeopardy with the impending returns of both Buchholz and Beckett, despite the fact that the knuckleballer posted a 3.25 ERA in five starts prior to getting roughed up in Tampa Bay last week.

Meanwhile, after a 1.19 strikeout-to-walk ratio in his first six starts, Matsuzaka has struck out 34 and walked just 14 in his last six starts, more than doubling that ratio to 2.43. With a 3.44 ERA since the beginning of June, Matsuzaka has consistently put the Red Sox in a position to win.

This is where history works against Wakefield. Since 2006, he has struggled to stay effective and healthy in the second half. From 2006 to 2009, he pitched nearly two and a half times as many innings in the first half than he did after the break. Over that span, his ERA jumped from 4.07 before the break to 5.60 after.

With the rest of the rotation locked up, that likely sends Wakefield back to the bullpen. That is, until a rotation spot opens up yet again.

Jeremy Lundblad is a researcher with ESPN Stats & Information. He provides statistical analysis for ESPNBoston.com.