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Why Jon Lester makes sense for Cubs

While watching the Chicago Cubs take on the Toronto Blue Jays on Tuesday night, you might want to change the television channel to get a glimpse of Oakland Athletics starter Jon Lester as he pitches against the White Sox.

Could Lester return to Chicago next season as a top-of-the-rotation starter for the Cubs?

A free agent at season's end, Lester has a good relationship with the Cubs' front office and is still seemingly in the prime of his career. We also know the Cubs are on the record saying they need top-end pitching.

Lester, 30, is 13-10 with a 2.54 ERA in 28 starts split between the Boston Red Sox and the Athletics. He's set to become a free agent for the first time in his career in a matter of weeks, and he will command top dollar. But here's the most important aspect of Lester: He's made a minimum of 31 starts every season since 2008. That should be very enticing to a team like the Cubs, which is likely to make at least one big splash in the free-agent pitching foray over the next two offseasons. You don't want to miss on a $100 million-plus investment.

"They [Cubs brass] always treated me with the utmost respect and class," Lester said earlier this season. "I have nothing but good things to say about them."

Theo Epstein was hired by the Boston Red Sox in 2002, the fall after Lester was drafted, but they won a World Series together in 2007. In 2009 Epstein signed him to a $44 million contract extension that ends this year. The Red Sox also saw Lester through while he dealt with non-Hodgkin Lymphoma in 2006.

"Obviously there's the familiarity with those guys," Lester said.

The Cubs may not want to get into a bidding war for Lester's services since they aren't in a win-at-all costs mode, nor are they one player away. But maybe the past connection with him is enough to forge a deal that fits their liking.

There's little doubt pitchers coming over from the American League have a history of success when they put on a National League uniform. The lineups are easier to navigate with the pitcher looming at the bottom of the order. Jason Hammel, Scott Feldman and Jake Arrieta are just the most recent examples.

Lester has been trending toward more fly balls than groundouts, but the sample size isn't large enough to be overly concerned. And as much as the wind blows in at Wrigley Field these days, giving up fly balls may not be as disastrous as it used to be.

If there was any 30-year-old, free-agent pitcher who you could predict success for in a Cubs uniform -- at potentially the right price -- Lester might be it. Plus, the Cubs would not have to give up a draft pick to sign him since he was traded midseason this year.

And if not Lester, maybe the Cubs should hold off on a major free-agent investment until after the 2015 season. That class is deeper. After the A's lefty, Max Scherzer of the Detroit Tigers is the only other true top-of-the-rotation pitcher going to the market this year. He's already reportedly turned down a $144 million extension from the Tigers. Can you see the Cubs going higher than that figure as soon as this offseason? Then again Lester might be asking for the same or more. No one knows.

After Lester and Scherzer, the pitching market drops. There's quality, such as Kansas City Royals starter James Shields and former Cub Hammel. But those pitchers probably don't change the narrative for 2015 as a developmental/building year. If things fall right, the Cubs could have an outside chance to contend for a playoff spot next season, but only if they grab a No. 1 pitcher and move everyone down a slot. Otherwise, it's more baby steps and wait until next year.

And that might be fine, too. Next year entails free-agents-to-be Jeff Samardzija, David Price, Jordan Zimmerman, Rick Porcello, Johnny Cueto and Yovani Gallardo. Of course, some might sign extensions with their current teams, but those names alone make for a better market than the ones who will become available in about seven weeks.

That means the Cubs should pursue Lester because he's the right guy for a lot of reasons. But they should do it on their terms with the mindset that they can always get another ace in 2015 if they can't get Lester now.

But Lester sure looks good at the moment.