Cubs

Will Cubs double down with another Jon Lester-level megadeal?

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Will Cubs double down with another Jon Lester-level megadeal?

When the Jordan Zimmermann trade rumors surfaced last offseason, there was a thought that he would set the meter at whatever Jon Lester got and leave it running.

The Washington Nationals talked extension and also took out an insurance policy against Zimmermann leaving, investing $210 million in Max Scherzer and preparing for their homegrown starter to sign somewhere else as a free agent.

Since the Cubs are big Zimmermann fans, do they double down on that six-year, $155 million contract and offer something in Lester’s neighborhood?

Does it make sense to go to the top of the market and try to put together a Scherzer-level megadeal for David Price?

And with all the uncertainty surrounding the team’s financial picture — at least in terms of how much of those new/postseason revenue streams will flow into baseball operations — it’s at least worth asking: Should the Cubs diversify their roster and not have such a top-heavy feel?

[MORE CUBS: Addison Russell made his presence felt during rookie year with Cubs]

The Cubs know they can’t stay this healthy or be that lucky in 2016. Realistically, there are no ready-for-impact pitchers in the minor-league pipeline, the biggest arms years away from potentially contributing.

This is also the time to be aggressive, because that window to contend will slam shut faster than you think. That win-now mentality could also mean building a trade for pitching around someone like Starlin Castro, Javier Baez or Jorge Soler.

Theo Epstein seemed to leave all options on the table during last week’s end-of-season news conference at Wrigley Field, where the team president looked ahead to a winter that could define his administration.

“The topic sentence is we would like to add more quality pitching,” Epstein said after watching Kyle Hendricks and Jason Hammel start Games 3 and 4 of a National League Championship Series the New York Mets led from start to finish.

Money talks, but the Cubs won’t have to sell a marquee free agent like Zimmermann or Price on a hope-and-change message, the blueprints for a renovated Wrigley Field and that group of blue-chip prospects.

Wrigleyville is under construction, guys want to play for Joe Maddon (though the manager’s pajama trips aren’t for everyone) and Kris Bryant, Kyle Schwarber and Addison Russell are now playoff-tested.

“Nobody expected us to be here,” Lester said after the Cubs got swept out of the NLCS. “Everybody just expected us to compete and be a part of something that was a step in the right direction. Now we’ve kind of put a stamp on that step (and) we’ve made believers out of people.”

The Cubs won 101 games after Opening Night, when the Cubs had bathroom issues, the Wrigley Field bleachers hadn’t opened yet, Lester still felt the aftereffects from a “dead arm” in spring training and ESPN highlighted the lefty’s issues throwing to first base and controlling the running game.

[MORE: Kris Bryant named Sporting News' NL Rookie of the Year]

Whoever joins the Cubs in 2016 won’t have the benefit of a training-wheels season or the goodwill generated during an out-of-nowhere playoff run.

“Now these guys (in the clubhouse) know,” Lester said. “These guys have seen it. They’ve been there. I don’t know if they ever knew they could do it. Now they know they can. I think stuff like this makes you want it more. You get to this point and (the Mets) pushed us aside.

“Maybe that means next year we’ll show up with the belief of winning and not the what-ifs of winning. Guys (should) have a little more swagger and go out and try to do the exact same thing. Hopefully, we’re not short at this point.”

Coming off two straight All-Star seasons where he showed up in the Cy Young Award voting, Zimmermann (13-10, 3.66 ERA) didn’t have the greatest walk year for an underachieving Nationals team that won only 83 games and got manager Matt Williams fired.

But Zimmermann still made 33 starts and topped 200 innings — showing the headstrong attitude the Cubs would appreciate — and he won’t turn 30 until the middle of next season.

Zimmermann is a self-made pitcher who came out of a Division III program — the University of Wisconsin-Stevens Point — and still keeps a home in Wisconsin.

The Nationals actually drafted Zimmermann with the 67th overall pick in the 2007 draft — a selection that had been part of the compensation package for the Cubs signing Alfonso Soriano.

Zimmermann is right-handed and had Tommy John surgery near the end of the 2009 season. The Cubs believe lefties typically age better and Lester (two World Series rings) also has more playoff experience than Zimmermann (12-plus postseason innings).

[NBC SHOP: Get your Cubs gear right here]

Lester wants another chance to show he’s a big-game pitcher after losing both of his playoff starts this October. But the Cubs have no regrets after Year 1 — 11-12, 3.34 ERA, 207 strikeouts in 205 innings — and would do the Lester deal all over again. Epstein said the Cubs would be fishing in those waters again this winter.

“You can fool people through the season and win games,” Lester said. “This is where you get exposed. And this is where you figure out how to truly win. We did it (through two rounds). We came up a little short (in the NLCS). But that’s only going to make us better.

“Hopefully, we get another chance at this and guys will come into spring training even more hungry. They know how to win now. They know how to compete, day in and day out. Guys will come in now and expect to be in this position.”

Cubs Talk Podcast: Manny Machado’s value and other Cubs offseason wish list items

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USA TODAY

Cubs Talk Podcast: Manny Machado’s value and other Cubs offseason wish list items

Did Manny Machado’s value take a hit at all after he openly admitted hustling isn’t his “cup of tea”? Our Cubs team (David Kaplan, Kelly Crull, Tony Andracki, Jeff Nelson) debate that, plus the potential fit of Machado or Bryce Harper for the 2019 Cubs and beyond.

The crew also runs down the top items on the Cubs’ offseason wish list – ranging from bullpen help to infield depth to a set leadoff hitter – in what may be the most impactful winter in Theo Epstein’s tenure in Chicago.

Listen to the podcast here or via the embedded player below:

The most underrated storyline of the Cubs offseason

The most underrated storyline of the Cubs offseason

There are plenty of intriguing Cubs storylines to monitor this offseason from their potential pursuit of the big free agents to any other changes that may come to the coaching staff or roster after a disappointing finish to the 2018 campaign.

But there's one question simmering under the radar in Cubs circles when it comes to this winter: How will the team solve the shortstop conundrum?

Just a few years ago, the Cubs had "too many" shortstops. Now, there are several different factors at play here that makes it a convoluted mess.

First: What will the Cubs do with Addison Russell? The embattled shortstop is in the midst of a suspension for domestic violence that will keep him off an MLB diamond for at least the first month of 2019.

Has Russell already played his last game with the Cubs? Will they trade him or send him packing in any other fashion this winter?

Theo Epstein mentioned several times he felt the organization needs to show support to the victim in the matter (Russell's ex-wife, Melisa) but also support for Russell. Does that mean they would keep him a part of the team at least through the early part of 2019?

Either way, Russell's days in Chicago are numbered and his play on the field took another big step back in 2018 as he fought through a hand injury and experienced a major dip in power. With his performance on the field and the off-field issues, it will be hard to justify a contract worth somewhere in the neighborhood of $4 million in his second year of arbitration (prorated, with a month's worth of pay taken out for the suspension).

Even if Russell is on the roster in 2019, Javy Baez is unquestionably the shortstop for at least the first month while Russell is on suspension. 

But what about beyond Baez if the Cubs want to give him a breather or disaster strikes and he's forced to miss time with an injury?

At the moment, there's nothing but question marks on the current Cubs shortstop depth chart throughout the entire organization and they're certainly going to need other options at the most important defensive position (outside of pitcher/catcher). 

There's David Bote, who subbed in for Baez at short once in September when Baez needed a break and Russell was on the disabled list. But while Bote's defense at third base and second base has opened eyes around the Cubs, he has only played 45 games at short across seven minor-league seasons, including 15 games in 2018. There's also the offensive question marks with the rookie, who hit just .176 with a .559 OPS and 40 strikeouts in 108 at-bats after that epic ultimate grand slam on Aug. 12.

The Cubs' other current shortstop options include Mike Freeman (a 31-year-old career minor-leaguer), Ben Zobrist (who will be 38 in 2019 and has played all of 13 innings at shortstop since 2014), Ryan Court (a 30-year-old career minor leaguer) and Chesny Young (a 26-year-old minor-leaguer who has posted a .616 OPS in 201 Triple-A games).

Maybe Joe Maddon would actually deploy Kris Bryant at shortstop in case of emergency like a Baez injury ("necessity is the mother of invention," as Maddon loves to say), but that seems a lot more like a fun talking point than a legit option at this current juncture.

So even if Russell sticks around, there's no way the Cubs can go into the first month of the season with just Baez and Bote as the only shortstop options on a team that with World Series or bust expectations.

The Cubs will need to acquire some shortstop depth this winter in some capacity, whether it's adding to the Triple-A Iowa roster or getting a veteran who can also back up other positions. Right now, the free agent pool of potential shortstops is pretty slim beyond Manny Machado.

Epstein always says he and his front office look to try to mitigate risk and analyze where things could go wrong to sink the Cubs' season and through that lense, shortstop is suddenly right up there behind adding more bullpen help this winter.