Winter baseball in Chicago usually revolves the debate between Cub and White Sox fans on whose team has better players or a better chance to win next season.
The Cubs path has been in a disappointing decline. The White Sox path has been rebuilding but stalling on development of starting pitchers.
A side by side comparison of the current 40 man roster players (2019 WAR). (*= injury year; R = Rookie Year).
SP1: Giolito (5.6) v. Hendricks (3.9)
SP2: Kopech (0.1*) v. Darvish (3.0)
SP3: Cease (-0.2) v. Lester (1.7)
SP4: Lopez (0.5) v. Quintana (0.7)
SP5: Rodon (0.1 *) v. Mills (1.0)
Giolito was clearly the best starter in Chicago. Kopech and Rodon were injured. Cease disappointed (but he may have been rushed to the majors). Hendricks and Darvish had good years. Lopez and Quintana are nearly wash. Lester is on the twilight of his pitching career. If you were going to give anyone an slight edge (3 to 2), it would be the White Sox with youth and potential vs. Cubs you saw what you have season. Rodon has experience Mills does not.
C: McCann (3.8) v. Contreras (3.1) McCann has a very quiet but better season than Contreras, who is now the trade bait rumor of the day.
1B: Abreu (2.4) v. Rizzo (3.9) Rizzo had to grind away to get his normal stat season; while Abreu surprised as an AL RBI machine with league leading 123.
2B: Sanchez (2.1) v. Hoerner (R) Sanchez won a gold glove and the Cubs second base position has been a black hole.
SS: Anderson (4.0) v. Baez (4.8) This is closer than people think, but the nod is still to Baez for his dynamic running ability and defense.
3B: Moncada (4.6) v Bryant (3.6). Moncada had a quiet monster season for the White Sox, significantly better than Bryant.
The infield selection yields in favor of the White Sox by a 3 to 2 margin.
LF: Jiminez (1.4) v. Schwarber (2.3) Schwarber had his best full season in LF, but he is still compared to Adam Dunn. Jiminez still has more potential. Both are not good defensively. It is almost a wash, but based upon last season the edge goes to Schwarber (who also may be trade bait).
CF: Robert (R) v. Almora (-1.0) It is not often that an unproven rookie would get the nod, but Robert is projected as a serious 5 tool stud. Almora has been terrible in his opportunities to win the CF spot.
RF: Garcia (1.6) v. Heyward (2.0). This position currently stands as almost a wash, but if you have to chose, Heyward for his defense.
The Cubs outfield squeaks out the nod. But both teams will have to address their weak outfield positions.
Closer: Colome (1.0) v. Kimbrel (-0.5) The White Sox did not trade their closer at the deadline even though he had value. He will have more value with a better team as the White Sox project in 2020. Kimbrel has been terrible. He was beyond rusty; he was bad. But the Cubs are stuck with him.
Overall, both bullpens are going to churned by both teams so you cannot gauge how it will turn out into after spring training.
In the current state, the Cubs and White Sox appear pretty even. The Cubs could continue to decline and the White Sox could rise to meet as .500 clubs in 2020. That would not be surprising.