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How Should The Cubs Deal From Strength?

What's the best way for the Cubs to use the assets they have to make deals this winter?

Jake Roth-USA TODAY Sports

When the Cubs let out that they were trying to win the division in 2015, it set off both bells of optimism and skepticism. Both are entirely justified. I'll still argue the "parallel tracks" comment has been being followed, though not to the satisfaction of many. The putting together a championship organization thing is best accomplished over a run of years. Many Chicago fans want results now. To balance the now and the process, neither can be followed exclusively, and moves are best made from a team's strengths. What strengths should the Cubs be dealing from this off-season?

An easy answer to the question is cash. The Cubs are a 'major market franchise'. The crosstown White Sox have broken open their piggy-bank to add David Robertson and Jeff Samardzija, without giving up too horribly much in return. The Cubs ought to aggressively acquire top-end pitching, especially if it only costs money, draft picks, and a few prospects, right?

A problem with that premise is, once spent, the prospect has no further value. Yeah, I saw your eyes roll there. "Tim won't give up any prospects, ever." Not even close to correct. More precisely, I want as many Cubs prospects as possible to provide major league value.

To delve into what I mean, I look back to the Cubs' Jacob Turner trade. Two teams (the Marlins and Rockies) made foolish decisions, and as a result the Cubs were given the gift of an eight-month trial on a rather recent No. 1 draft selection. Not only did it require the Marlins to misjudge their playoff likelihood, but it required the Rockies (who would soon acquire Chris Rusin off waivers) to not try the same strategy on Turner.

Long story short, the Cubs added Turner for Midwest League relievers Tyler Bremer and Jose Arias. About the only way you would have seen the latter two pitch was by taking in a Kane County Cougars game last year. Honesty compels me to admit that Turner may be broken beyond repair as far as being a solid MLB pitcher. The price for participating in the exercise was awfully cheap, however.

What is the strength of the Cubs system?

Again, an easy answer is "Kris Bryant, Addison Russell, Jorge Soler, and Javier Baez if he learns to hit the ball more."

However, I don't see that as the strength. The strength of the Cubs system, to me, isn't written on a lineup card. The strength of the Cubs system doesn't write out a line-up card. The strength of the Cubs system is why Jon Lester is contemplating coming to a team with a recent history of losing baseball games. The Cubs strength is why Joe Maddon and Dave Martinez preceded Ryan Dempster to the club.

The strength of the Cubs system is the system the Cubs have in place. It isn't magic-y goodness that decided Kris Bryant or Kyle Schwarber should be the Cubs' most recent top picks. The strength of the Cubs system is that the key people in the system broke down the key information and decided that a slugger third baseman/outfielder with no history of defensive excellence would be a good second overall pick in the draft. It's the same people deciding that an offensive player without an obvious defensive home would be a good fourth selection.

And, for goodness sake, it isn't just Theo Epstein. If it were, any bunch of dolts could push guys through a system and make players better. Epstein is very good at putting people in spots where they can succeed. And that they can help others succeed.

"Yeah, yeah. So what does this have to do with the Winter Meetings or the offseason in general?"

The Cubs are deep in prospects at the upper and lower levels because their executives and coaches seem to be able to elicit quality from players. At some point, getting players like Bryant and Schwarber in the draft might go away. What the team is flush with now is depth. There are more than a few teams that could plug someone from the Cubs second twenty into their top eight prospects. It would be a wise idea to use these resources wisely.

One of the current possibilities seems to be acquiring Miguel Montero from Arizona. Twitter rumors had "two A-level pitchers" as the potential return. While the reports didn't have instant credibility, these are the trades the Cubs really ought to consider.

No, I'm not Coo-Coo for Cocoa Puffs over Montero. However, if remote options like Daury Torrez can bring in major league talent, especially without denting the prospect supply very badly, those moves should be considered.

What is it teams want now? Reasonably good talent with team control attached. For instance, Billy Beane has apparently flipped Samardzija for Marcus Semien and two other prospects. Teams do funny things these days, especially to get cost controlled talent.

The Cubs have already upgraded their pitching this week by adding Jason Hammel. The plank is getting shorter for Edwin Jackson. Jon Lester could be the next player incoming and possibly without tacking on a seventh season to the deal. The Reds and Brewers will likely be in the rear view mirror rather soon. The goal should continue to be moves that are wise, not flashy. (Though wise moves that are flashy are better, admittedly.)

The Cubs front office has likely pegged eight or ten players they would like to trade for. "Like who? Who are they going to get?" I'd imagine in May 2013, two of the guys they were intrigued by were Jakes Turner and Arrieta. As time and circumstance permitted, they added them both. On the cheap.

Whether Montero was on that list, I don't know. However, as names are being bandied about, the Cubs are probably trying to get access to a few players their scouts really like. Not only is it illegal for them to mention what players are on 'the list' (tampering), it's also bad business.

An honest effort has been given toward adding Lester, as had been made with others before. The team's situation is making the case to come to Wrigley more compelling as time progresses. That should continue. I still expect another "They did it again" move this off-season. With more teams re-building, and the Cubs holding a horde of prospects, it's very possible.

The Cubs will be more competitive in 2015. Doubtless, some will cry "Not competitive enough." Last year, the team had plenty of question marks. This year, a couple fewer. Next off-season, the team will have fewer still, probably. As a desirable team has only a few question marks, they become a destination location for the best at those spots. This is about to get fun.

And even sooner if Jon Lester signs for a reasonable contract.