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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?

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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).

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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: Cubs offense takes a step in right direction, when will rotation follow?

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USA TODAY

Cubs Talk Podcast: Cubs offense takes a step in right direction, when will rotation follow?

For the first time in almost two weeks, the Cubs offense started to look more like the team we know they can be in Wednesday afternoon's victory over the Brewers. But when will the starting rotation follow? Kyle Hendricks pitched better than his stat line once again, but it's getting late in the season to continue to use that rationale for any Cubs starter.

Kelly Crull and Tony Andracki break down the Cubs-Brewers series and Kelly sits down with David Bote for a 1-on-1 chat about his whirlwind week. Leila Rahimi also catches up with MLB Network's Dan Plesac to get his thoughts on Javy Báez's place in the NL MVP race, how the Central division is shaping up and X-factors for the Cubs and Brewers down the stretch.

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

SportsTalk Live Podcast: Is Milwaukee the biggest NL Central threat to the Cubs?

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USA TODAY

SportsTalk Live Podcast: Is Milwaukee the biggest NL Central threat to the Cubs?

Phil Rogers, Jim Litke and Harry Teinowitz join Kap on the panel. Joe Maddon tweaks the lineup and the Cubs offense explodes to beat the Brewers. Is Milwaukee still the Cubs’ biggest threat in the Central? And is Javy Baez still the Cubs’ MVP?

Plus Roquan Smith puts on the pads to practice but will he have them on in Week 1 at Lambeau?  

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