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CHICAGO CUBS
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Chicagoans live in a perpetual state of denial. We love everything about our city and won’t tolerate one negative comment from an outsider. But as November approaches, we mutter under our breaths, complaining about the impending cataclysmic weather pattern (seriously, must the Polar Vortex really make a return visit?) that’s slowly coming our way.

The same can be said of many Cubs fans and their protective nature of the current front office. This franchise has been particularly poor on the field of late, finishing in fifth place five years, never within 16 games of winning the division. Yet one bad word from an outsider about Theo Epstein and company’s plan to reshape the organization would result in a Twitter takedown of epic proportions.

Still, there was always that nagging feeling that the team wouldn’t open up the coffers when the time came. Whether it was Ricketts being stingy, or Epstein being gun-shy after handing out some highly publicized, albatross-like contracts in Boston, there were questions as to whether this group would do what it took to nab that big name. Just as finishing fifth in the standings became a familiar feeling for the Cubs, finishing second for free agent targets became the norm: Yoenis Cespedes, Hyun-Jin Ryu, Anibal Sanchez, Masahiro Tanaka, and, most recently, Russell Martin. The North Siders were repeatedly falling just short of impact talent that could change the trajectory of the current rebuild.

"When there's a potential impact player involved, it does shape, a little bit, the course of your short-term thinking," Epstein said last Friday when meeting with Chicago media. "If you get a player who makes a significant difference in the standings, then you prioritize creating a winning roster immediately around that player. Where as if the offseason goes in a slightly different direction, you just continue to build more organically, you continue to think a little bit longer term. And it's not an extreme, it's not two absolutes, but obviously you look at things a little bit differently."

Sure enough, it appears the Cubs will be changing their short view as they ended that unfortunate second-place trend late Tuesday night in San Diego, when reports came out that they’d nabbed Jon Lester on a six-year, $155 million deal. If bringing in Joe Maddon was the Cubs ordering off the expensive side of the menu, acquiring Lester was proof that they weren’t going to skip out on the bill.

“I think we’ve done a nice job of building up the organization to a really healthy place where we can be aggressive,” Epstein said last week. “And we are being aggressive, and we’ll continue to be aggressive, but we’re not going to enter into any one negotiation as if it’s do or die.”

Obviously they followed through on their promise of being aggressive and Lester was paid quite handsomely. But it's important to keep in mind that he’s coming off one of the best walk years ever, making the contract he signed with the Cubs not feel as onerous as it may at first blush.

“There are no bargains in the free agent market for established players. If you’re going to get a player, the other 29 teams are going to point at you and say you overpaid,” Esptein recently stated. “That’s the reality. There’s so much TV money in the game these days, it’s not two or three teams competing for an elite player, it’s 10 or 12. That’s the reality right now, so you have to be prepared for it. It’s not for the faint of heart.”

According to Jeff Passan, Lester wasn’t looking to have his ego fed during the free agency courting period.

“The thing I liked about ‘em is it wasn’t forced and wasn’t a sales pitch,” Lester said after his meeting with the Cubs. “It was like, ‘This is what we can do.’ I don’t want BS. I don’t want show. I don’t want glitz and glamour. I don’t want to walk out to the field with your name and number on the JumboTron. I’m not 18 anymore. I want you to tell me what you can do for me and my family.”

The Cubs front office avoided any over-the-top gestures and used the relationship they’d built with Lester over the years to help answer any question about whether this group can lure the top-tier talent available in free agency. So the next obvious question is, could this team compete as early as 2015?

“The Cubs are in a really nice spot compared to where we were a few years ago, I think we’re going to continue to get healthier and healthier as an organization,” Esptein said, prior to acquiring Lester. “And if we’re successful in one or two of the things we’re trying to do this winter, then we’re going to be very competitive, very soon.”

Adding the veteran lefty certainly makes it that much more attainable, as does bringing in Miguel Montero and Jason Hammel. But when looking at their current roster, there aren’t many sure things. Jake Arrieta has improved his mechanics and appears to have really figured things out mentally; his breakout certainly feels real, but until he goes out and does it for 200-plus innings in 2015, some doubt will linger. Anthony Rizzo was one of the top bats in the National League, but is that where his career settles, or is he truly a level below? Was Starlin Castro’s strong rebound just one more temporary jag in an inconsistent career? Will Javier Baez and Arismendy Alcantara be able to figure it out at the plate after rough starts to their big-league careers? Can Jorge Soler build off his impressive debut or was the rough patch he suffered through in his final few weeks a sign of things to come? How long will Kris Bryant’s adjustment period be? Even the other recent acquisitions all come with question marks. The list of uncertainties is long for the Cubs, but it’s clear that the upside is quite high.

Cubs fans should feel justified in believing this team can make a run in 2015, especially if, as Epstein alluded to above, they can add another impact piece, in particular, a veteran bat to immediately lengthen the lineup. However, the latter is hardly guaranteed, and it’s more likely that a few veteran, part-time players will be added to strengthen the clubhouse and the bench. There’s a lot of volatility to the current roster, so while it’s nice to have some hope at Wrigley, it’s also likely that 2015 is just the unlocking of a window that should be wide open come 2016.

Either way, this is a team on the rise, which has been obvious to anyone who's been paying attention over the last 18 months. The arrival of Lester to Chicago will certainly warm up the winter months for anxious Cubs fans who can finally at least hope for a winner come April.