Ideal Trade Scenarios for the Cubs to Focus on Pulling off This Offseason

Linked to major free agents this offseason like Jon Lester and Russell Martin, the Chicago Cubs are expected to make a big splash this winter in one way or another. Signing free agents is surely a way to improve the team quickly, but teams can also do that via trade.

Even though it's hard to know which rumors to listen to, the Cubs have already been linked to trade scenarios involving Cole Hamels and Jordan Zimmermann (although the Zimmermann report was later discredited).

There are plenty of other trade possibilities out there for the North Siders to pull off before the offseason fun is over. These three trades in particular would make the Cubs considerably better without sacrificing the vision president Theo Epstein and general manager Jed Hoyer have worked over the last three years to create.

Dodgers: Carl Crawford

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Before getting upset that Carl Crawford would cost the Cubs too much money, realize the Los Angeles Dodgers are really desperate to move the contract of Crawford, Andre Ethier or Matt Kemp. That means they're going to be flexible on eating a large portion of the contract belonging to any player they trade.

According to Ken Rosenthal of Fox Sports on Twitter, the amount of money the Dodgers eat is contingent on the return they get. This makes sense. If they get a good package of prospects, they may eat a majority of the deal. If they don't get such a great prospect package, they're going to be less willing to eat much, if any, money.

Without the Dodgers paying any of the salary, the Cubs would owe Crawford $63 million over the next three years. Luckily for the Cubs, they have plenty of prospects to work with, and they may not even have to give up an elite prospect. However, only the Dodgers know exactly what they want in a trade, so it could take an elite prospect to get Crawford anyway. 

This talk isn't just conjecture, either. Bruce Levine of CBS Chicago says Crawford may, in fact, be on the Cubs' radar. As Levine notes in his piece, Crawford would give the Cubs a left-handed hitter, an outfielder and a leadoff hitter all in one. That's a pretty valuable package if he can stay healthy (big if).

If the Cubs can afford to package two very good, but not elite, prospects for Crawford, they should strongly consider it. Outfielder Billy McKinney and first baseman Dan Vogelbach are options to group together in a deal.

Both are young and left-handed, which has to be appealing to the Dodgers. By the time McKinney is major league ready, current outfielder Kemp will have likely moved on or been traded by then. With an aging Adrian Gonzalez at first base, having his replacement waiting in the wings makes sense for the Dodgers.

The prospect and money tradeoff is what it could come down to. If the Cubs can put together a package of prospects that brings down Crawford's annual cost to the team to between $10-12 million, they should pull the trigger.

Braves: B.J. Upton

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Often, when teams have struggling contributors that are locked up for multiple years, they will look to swap those players—if for no other reason than to give them a change of scenery. The Cubs and Atlanta Braves tried to do exactly that at the trade deadline when they discussed a possible swap of Edwin Jackson for B.J. Upton. 

Both teams are justifiably upset with their underperformers. Jackson, who posted a 6.33 ERA in 2014, is due $22 million over the next two years. Upton, meanwhile, is due around $15 million, $16 million and $17 million in each of the next three seasons, respectively, despite hitting .184 in 2013 and .208 in 2014.

Clearly, both players are overpaid, but each would be more valuable in the other uniform. The Braves could use pitching, especially if they lose starter Ervin Santana in free agency this winter. While he would cost a bit more than Jackson, Upton would provide an outfielder the Cubs need to bridge the gap between their current placeholders and up-and-coming prospects.

Since they're already tied to Jackson, swapping contracts wouldn't make the Cubs that much worse off. With the team hoping to sign free-agent pitchers this offseason, clearing space in the rotation is a must. Obviously, that starts with the worst guy there.

Really, the best-case scenario here is that Upton returns to form and becomes a contributor for a competitive Cubs team. In the worst-case scenario, he doesn't get back to form, and the Cubs pay $9 million more than they would have between 2015-16 and then an additional $17 million in 2017. 

Clearly, the 2017 portion of the contract is the riskiest. But by then, the team may have alternative options to replace Upton if he struggles. Those options would be prospects still on rookie contracts, so the $17 million owed to Upton wouldn't be as big since it would be for only one season.

Boston Red Sox: Yoenis Cespedes

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Once again, the Cubs could use an outfielder. Yoenis Cespedes fits the mold of what would fit into the Cubs' lineup. A few weeks ago, Nick Cafardo of The Boston Globe mentioned that the Boston Red Sox could make the Cuban outfielder available. Even though some reports now say the Red Sox would like to hold onto Cespedes, no player is untradeable. 

The trouble with this potential deal is that the Red Sox already have a lot of hitting prospects, so the Cubs may not be able to offer much that Boston doesn't already have. That's why, of all the potential trades on this list, this is the least likely to happen.

However, the option is intriguing. Surely, the Cubs would have to be assured he would sign an extension since he becomes a free agent next offseason.