The Cubs just finished up what will go down as one of the more memorable seasons in recent franchise history. Yes, it ended at the hands of the hated New York Mets (again), but don’t let that take anything away from what this team did this year. Did anyone honestly expect the Cubs to make the playoffs? Maybe, maybe not. Did anyone think they’d win 97 games? Absolutely not. Yet they did, and they went on to win the NL Wild Card game and then the NLDS. There’s no way that this season can be viewed as anything less than encouraging and a sign of what may lay ahead of us down the road.

Looking down that road, it’s pretty clear that the Cubs need to add to their current roster if they truly want to contend for a World Series championship. And lucky for them, this offseason’s free agent class is pretty jam packed with star players.

Without being completely unreasonable, here’s a look at the top five players the Cubs may target this winter in order of importance.

1. David Price: Price is one of the game’s best left-handed starting pitchers, and if it wasn’t for Clayton Kershaw, he’d likely be the best. While his career postseason numbers are less than ideal, his talent and ability to dominate any and every game make him possibly the number one free agent pitcher this offseason. The Cubs, without any doubt, must add another quality starter to their rotation. Their lack of starting depth is one reason why they were swept by the Mets. Having a 1-2-3 punch of Arrieta, Price, and Lester would be huge and scary. Add in that Price has made some comments in the past about possibly wanting to join the Cubs and reunite with Joe Maddon, and this scenario is far from unlikely.
2. Zack Greinke: No one was expecting Greinke to be a free agent this winter, but he is after opting out of the remainder of his contract with the Dodgers. You may be asking why he isn’t ahead of Price on this list, and the reason for that is his age (Price is two years younger) and money. Greinke is likely to sign for a higher dollar amount than Price given what he just did this season, and the Cubs aren’t going to want to pay that amount if Price is still a possibility. Otherwise, they’d likely go for Greinke first. One thing is certain, however, and that is that the Cubs will not sign both Price and Greinke. If they lose out on one, they’ll pursue the other. If they sign one, they’ll give up on the other. The Cubs will go after a starting pitcher, likely one of these two, before anyone else.
3. Dexter Fowler: Fowler is set to become a UFA, and many believe he played himself into a big contract this season. Depending on what the market becomes for Fowler and the numbers of years and dollar amounts being thrown around are, the Cubs may or may not try to re-sign him. They’ll need to sign a center fielder one way or another, whether it’s Fowler or not. They would like to bring him back, but won’t overpay him to do so.
4. Jason Heyward: This is a tricky situation. Odds are that Heyward will get more money than Fowler, but Heyward brings a bit more to the table too. He’s not a natural center fielder, but can play the position. Whether the Cubs choose to go this route before the Fowler route remains unknown. Like Fowler though, the Cubs will not overpay for Heyward. If he’s asking for a ridiculous contract, you can count the Cubs out. It all depends on whether or not Theo Epstein and Jed Hoyer believe Heyward can be a full time center fielder, and an effective one. Another thing to think about with Heyward is if the Cubs go after him over Fowler, they are now without a lead off hitter. There’s positives and negatives to Heyward.
5. Jordan Zimmerman: It isn’t out of the question that the Cubs could potentially sign Price or Greinke, as well as Zimmerman. He likely pitched himself out of a huge deal this year (3.66 ERA and a career high WHIP), so his price may be more affordable now than say a year ago. Signing him along with one of the two previously mentioned pitchers would give the Cubs a formidable rotation and one that could be deadly in the playoffs. If the Cubs can sign Price or Greinke, a potential Zimmerman signing could be the key offseason acquisition.

Starting pitching is one hundred percent the first area the Cubs will address this offseason. Once they sign a quality starter, they’ll likely shift their focus to a center fielder, and then back to another starting pitcher. If the Cubs are able to sign any of the three guys I listed above, that will be big. If they can sign two or even three of them, that’ll be massive. I wouldn’t rule out signing three of them either as long as the money involved isn’t an astronomical amount. Epstein, Hoyer, and Ricketts are determined to bring a World Series championship to the franchise, and they’ll go to extreme, but reasonable, measures to do so.

This should be another fun offseason for the Cubs, and it’s only the beginning.