Could the Chicago Cubs attempt to woo Jon Lester this winter?

It’s well-documented that the Chicago Cubs’ farm system is one of – if not the best in all of Major League Baseball.

With the likes of Javier Baez, Jorge Soler, Kris Bryant, Albert Almora, Addison Russell and Kyle Schwarber – several of whom haven’t even reached the big leagues yet – in the system, it’s not hard to understand why the Cubs’ fan base is so excited about the future. However, one of the glaring holes left in the organization moving forward is impact starting pitching.

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Currently, the club’s rotation features Travis Wood, Kyle Hendricks, Jake Arrieta, Tsuyoshi Wada, Felix Doubront and Jacob Turner. This list, while certainly showing some promise, is nowhere near the rotation of a playoff contender. To be blunt, it’s not even the rotation of a playoff hopeful.

Wood, after making the NL All-Star team in 2013, has taken a major step backward in 2014. The southpaw has a 5.15 earned run average in 29 starts – over two runs higher than last season, when he eclipsed the 200-inning plateau for the first time in his big league career – and his 3.9 walks per nine is a career-worst. His struggles have placed more of the burden on the team’s young starters who, in the season’s final month, are all looking to make an impression for 2015.

Arrieta has been the staff ace since Jeff Samardzija and Jason Hammel were traded to Oakland prior to the All-Star Break, but he has been a different pitcher in the second half. Wada has been impressive in 10 starts, pitching to a 2.95 ERA and 1.091 WHIP across 55 innings, but whether or not he can be counted on for an entire season remains to be seen. Doubront has just a handful of starts under his belt with Chicago and both he and Turner are still major works-in-progress for pitching coach Chris Bosio.

That brings us to Jon Lester.

The former World Series champion has strong ties to the Chicago front office, as is pointed out by ESPN Chicago’s Jesse Rogers in a recent piece.

Rogers believes the Cubs could be in the hunt for the southpaw this offseason, when the current Oakland Athletics pitcher will reach free agency, likely commanding a contract north of $100 million. As he points out, Lester has been remarkably consistent – making at least 31 starts every year since 2008. He’s also not tied to any draft pick compensation, given he was traded from Boston to Oakland midseason. This will no doubt make him more attractive to a young team like Chicago, which relies heavily on success in the draft each year.

As noted, Rogers believes Lester is one of the safest investments Theo Epstein and Jed Hoyer could make this offseason:

"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."

While I agree with Rogers – it’s not hard to imagine that the bidding war could push the contract offered to Lester far higher than need be. He’s maintained that money will not be the deciding factor in his decision-making process this winter; but really, who could blame the guy?

"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."

If the Cubs decide to let the teams in win-now mode throw money at Lester this winter and wait things out until after the 2015 season, the starting pitching class is one of the strongest in recent memory. Some of the more eye-catching names include Jordan Zimmerman of the Washington Nationals, Rick Porcello and David Price of the Detroit Tigers, former Cub and current Oakland starter Jeff Samardzija and Cincinnati Reds’ hurlers Johnny Cueto and Mat Latos – to name a few.

If the Cubs can add a solid middle-of-the-rotation piece this winter, the front office could be set up to make big moves next winter. However, the likes of Lester, Max Scherzer and James Shields could prove to be too much to resist in the months to come. Adding any of them would be a major piece for the organization moving forward – and while the price tag on many of these premier pitchers will be high in the next two offseason – impact pitching is rare and a major need on the team’s World Series shopping list.

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