5.) Who plays center-field?
Dexter Fowler played center for the Cubs in 2015, and earned $9.5 million for his efforts. Fowler hit the ball well in the leadoff spot, and gave the Cubs a .250/.346/.411 line with 17 home runs and 46 RBIs. He also topped 20 stolen bases for the first time since 2009. Fowler was a good captain of the outfield, and handled the tricky Wrigley Field winds well. The Cubs did not surround Fowler with the most outstanding defensive corner outfielders, but he compensated nicely. Fowler will get a bump in salary and a multi-year deal, but most likely with a different team.
That leaves the Cubs in need of a center fielder. Austin Jackson, who the Cubs traded for in August, is a possibility. Jackson’s market in free agency will not be as robust as Fowler’s. The Cubs may even be able to get him back on a two-year deal. Fowler and Jackson are very similar players (Fowler is actually Jackson’s number one comparable player according to Baseball-Reference’s similarity score — 956 is pretty darn similar). Jackson is coming off a weaker year than Fowler, and has now played for four teams in the past two years. Jackson would be an unexciting re-signing for the Cubs.
A more interesting name to consider is Javier Baez. The middle infielder could be converted to center-field with a little practice. He’s open to the idea, and is on record saying so. Baez is athletic enough to learn the outfield. It may not be the prettiest thing in the world the first few months, but it can’t be any worse than Alfonso Soriano. Wrigley Field is not huge, and a converted infielder with enough athletic ability should acquit himself well tracking down flies.