For Cubs, winter meetings will be all about the hunt for pitching 

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As the Cubs prepare for the winter meetings outside Washington, D.C., their messaging might as well be: It’s the pitching, stupid.

This is an arms race that will never end, the Cubs trying to defend their first World Series title in 108 years, build out a bullpen that looked pretty thin by November and target the kind of young starter who could help anchor their rotation for years to come, ensuring Wrigleyville remains baseball’s biggest party.

The Cubs signed Brian Duensing to a one-year, $2 million contract on Friday, placing a small bet on a lefty specialist who spent parts of last season on the Triple-A level but made a good enough impression during his 13-plus innings with the Baltimore Orioles.

As executives, scouts, agents and reporters begin to flood into National Harbor on Sunday, the Cubs will intensify their search for pitching, everything from headliners to insurance policies to prospects.

“That’s been the significant bulk of our efforts,” general manager Jed Hoyer said, “It’s definitely not going to be through lack of trying on our part to make that kind of deal. That’s now. That’s at the deadline.”  

The Cubs are preparing for Opening Day 2018, when Jake Arrieta will probably be in a different uniform after signing his megadeal, John Lackey might be kicking back in Texas and enjoying retirement and Jon Lester will be 34 years old with maybe 2,300 innings on his odometer. 

The Cubs have unwavering faith in their pitching infrastructure at the major-league level, from the scouting and analytic perspectives that identified the right sign-and-flip deals during the rebuilding years to the coaching staff that helped mold Kyle Hendricks into a Cy Young Award finalist and a World Series Game 7 starter.

Mike Montgomery notched the final out against the Cleveland Indians and the Cubs see him as their next big project. The lefty checks so many of their boxes, from age (27) to size (6-foot-5) to pedigree (former first-round pick/top prospect) to the change-of-scenery confidence boost/mental reset.

Forget about the White Sox trading Chris Sale to the North Side and don’t just think about obvious names or trade partners. Maybe it’s making a deal for a guy you never heard of before and sifting through the non-tender bin. (As expected, the Cubs offered contracts to arbitration-eligible pitchers Arrieta, Hector Rondon, Pedro Strop and Justin Grimm before Friday’s deadline. Their 40-man roster stands at 35 after non-tendering lefties Gerardo Concepcion and Zac Rosscup, right-hander Conor Mullee and infielder Christian Villanueva.)

Remember how team president Theo Epstein framed the Montgomery trade with the Seattle Mariners this summer – comparing him to All-Star reliever Andrew Miller – and that gives you an idea of how they can address their pitching deficit this winter. 

“If your scouts do a good job of identifying the guys who are trending in the right direction – and you’re willing to take a shot – sometimes there’s a big payoff at the end,” Epstein said.   

While the Cubs did Jason Hammel a favor by cutting him loose and allowing him to explore the market as one of the best pitchers in an extremely weak class of free agents, Montgomery has only 23 big-league starts on his resume. 

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The Cubs had five starters make at least 29 starts this year, while four starters accounted for 30-plus starts in 2015, a remarkable run that led to 200 wins.

“As we’ve talked about so many times,” Hoyer said, “we do have an imbalance in our organization – hitting vs. pitching – and we’re trying to make sure we can accumulate as much pitching depth as possible. 

“We were very healthy this year, which was wonderful and a big part of why we won the World Series. I don’t think you can always count on that kind of health every single year. Building up a reservoir of depth – preferably guys you can option (to the minors) – is something (we’re trying) to accomplish.”  

The Cubs have Jorge Soler stuck in a crowded outfield plus the types of interesting prospects who appear to be blocked – catcher Victor Caratini, third baseman Jeimer Candelario, infielder/outfielder Ian Happ – to make relatively painless trades for pitching (if not the kind of blockbuster deal that dominates coverage of the winter meetings).

Lefty reliever Brett Cecil getting a four-year, $30.5 million deal and no-trade protection from the St. Louis Cardinals became another sign of how shallow this free-agent pool is for starting pitchers and a reflection of a postseason where the bullpen became a major storyline.

The idea of Kenley Jansen intrigues the Cubs – and Aroldis Chapman made a favorable impression during his three-plus months with the team – but Epstein’s front office already made the major upgrades for 2017 by spending nearly $290 million on free agents after the 2015 playoff run. Philosophically, the Cubs also see smarter long-term investments than trying to win a bidding war for a guy who might throw 70 innings a year. 

With that in mind, the Cubs could get creative and have looked at free agent Greg Holland, a two-time All-Star closer with the Kansas City Royals who didn’t pitch this year after having Tommy John surgery on his right elbow.  

Remember that Chapman left the New York Yankees and joined a team that had a 56-1 record when leading entering the ninth inning. If Hector Rondon, Pedro Strop and Carl Edwards Jr. can’t handle the late shifts, then the Cubs could always go out and trade for another closer in the middle of a pennant race.    

The Cubs have the luxuries of time, zero pressure from ownership, their fan base or the Chicago media and a stacked, American League-style lineup. 

“Right now, we could go play from an offensive standpoint and feel very good about our group,” Hoyer said. “We’re going to still continue to look to improve the depth in our bullpen, improve the depth in our starting rotation. Those are things that probably never go away. You probably never stop trying to build that depth.” 

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