Cespedes or Bust for White Sox?

Photo Credits: Jon Durr, Getty Images

Photo Credits: Jon Durr, Getty Images

When the White Sox traded three of their best prospects for star third baseman Todd Frazier last month, it was evident that the Sox engaged in “win now” mode. In order to bring Frazier to town, the Sox had to part ways with three of their best prospects – Trayce Thompson, Frankie Montas, and Micah Johnson.

Heading into the offseason, the Sox had a lot of holes on their roster that needed to be filled. Those holes were primarily in the infield, and they were all immediately addressed. As mentioned above, Frazier was traded for to upgrade third base; and the holes at second base and catcher were patched up with the additions of Brett Lawrie, Alex Avila, and Dioner Navarro.

Many baseball analysts will tell you that the Sox, as their roster stands now, are one upgrade away from being considered a legitimate playoff contender. That upgrade, that Sox fans have been desperately longing for since last month, is needed in the outfield.

With three of the four big name free agent outfielders (Jason Heyward, Justin Upton, and Alex Gordon) now off the market, Yoenis Cespedes is the lone wolf in the elite level outfield market.

Cespedes will not come cheap. He will likely require a contract of at least five years and at least $100 million which leaves the Sox with the debate of whether or not they should go to such lengths to sign the 30-year-old.

It has been reported by multiple sources that the Sox are not willing to extend an offer to Cespedes beyond three years. Sure, such limitations make perfect sense from the White Sox perspective. At age 30, Cespedes likely has 2 or 3 more years left of above average performance in his tank. The Sox also have a nice 2-3 year window with Frazier, Lawrie, and Melky Cabrera all under contract through 2017, and David Robertson under contract through 2018.

But obviously, there are two sides to each deal. From Cespedes’ perspective, why would he want to enter free agency again at age 33? The back end of a five or six year deal that he could sign this offseason would likely pay him a lot more money than what he would earn beyond 2018 if he signed a new deal three years from now.

If the Sox manage to find a way to sign Cespedes this winter, their roster would be primed for a playoff push. Their lineup would instantly become one of the best in baseball. If you accompany an already productive pitching staff with a lineup that features Jose Abreu, Frazier, and Cespedes at the 3-4-5, there is no reason to believe that the Sox can’t win at least 90 games.

The downside of signing Cespedes to a long-term deal is that paying him around $18-$20 million in his age 33 and 34 seasons (2019 and 2020) could become a huge liability. What if the Sox didn’t have the money to lock up Carlos Rodon, Tim Anderson, or Carson Fulmer three years from now because they have so much money still on the books with an aging Cespedes?

All things considered, I think that presenting a 5-6 year offer to Cespedes makes more sense than standing pat. As mentioned above, the Sox made it clear that they want to win now when they traded for Frazier. They have two superstars in Chris Sale and Jose Abreu who are in the primes of their careers. They have a top-5 third baseman in Frazier. They have a top-10 centerfielder in Adam Eaton. They have a top-25 pitcher in Jose Quintana as their #2, and an emerging Carlos Rodon as their #3.

Have you ever heard a Little League coach tell one of his players, “If you’re gonna swing, SWING!” when the player is indecisive at the plate? Well, I couldn’t think of a baseball-related metaphor that is more fitting for the White Sox offseason.

Jerry Reinsdorf, Rick Hahn, if you’re gonna swing, SWING!!!