The first installment of the 2020 Wintrust Crosstown Series will kick off Friday at Wrigley Field as the upstart White Sox come to town.

This is not the same White Sox team that lost 89 games a season ago – they came into 2020 set on contending and have jumped out to a 13-11 start in the AL Central.

This is the first time in a while where both Chicago teams have eyes on the postseason heading into a Crosstown showdown and we took the opportunity to break down how the Sox and Cubs stack up against each other this season.

[Programming Note: Watch every Crosstown Series game on Marquee Sports Network with coverage continuing Saturday at 6 p.m. with Cubs Live!]

CATCHING

Andracki: Yasmani Grandal is a great two-way catcher and a really important signing for a young White Sox team. But the Cubs have the best catching tandem in baseball, in my opinion. (Is that opinion biased? Probably…)

Willson Contreras and Victor Caratini have split time between catching and the DH spot, working closely with the pitching staff. Contreras’ relationship with Jon Lester and Caratini’s dynamic with Yu Darvish have both proven successful in the early going. Neither Contreras nor Grandal have truly gotten going offensively yet this year, but that could very easily happen for both players this weekend.

Grandal was a thorn in the Cubs’ side last season as a member of the Brewers. He posted a .384 on-base percentage and hit 4 homers against Cubs pitching.

Martinez: You can pick either the White Sox or Cubs as having the better catching corps, but there’s no denying the best catching tandems in baseball reside in the Windy City. Grandal is arguably the premier great two-way catcher, but it’s easy to forget James McCann, who was an All-Star in 2019. 

The duo, plus Zack Collins, have combined to provide an .855 OPS for the White Sox behind the plate. Conversely, Willson Contreras, Victor Caratini and Josh Phegley have combined for a .792 OPS. 

Regardless of the offensive output, the Cubs catchers take the slight advantage, given they’ve caught and managed one of the best starting rotations in the game. Caratini and Contreras have been instrumental in their catching of Darvish and Lester, respectively. 

INFIELD

Andracki: This might be the toughest call to try to pick the best group between the two Windy City squads. Each team features a Big 3 at shortstop and the corner spots, with the trio hitting in the first few positions in the lineup for both teams. 

The difference right now is the level at which the stars are playing heading into the weekend. Tim Anderson has been incredible while Yoán Moncada and José Abreu have continued their typical production. For the Cubs, only Anthony Rizzo is really at that level. Javy Báez has been slumping offensively and Kris Bryant’s status for the weekend is currently unknown after he received a shot in his ailing left wrist. 

Martinez: On paper, this is arguably the hardest one to pick. The White Sox infield is a mixture of proven veterans, players on the rise and some unknown. 

Anderson is proving his AL Batting Title in 2019 was no fluke — he’s hitting .371 with a whopping 1.126 OPS. He’s improved defensively, too, this season, which one of the knocks on his game last year. While Báez has the longer track record and higher career numbers (Báez – .788 OPS, 113 HR, 17.0 WAR vs. Anderson .749 OPS, 69 HR, 9.7 WAR), Anderson has been outperforming El Mago this season. 

Abreu is a solid veteran and seems to be having another solid season. Rizzo, like Abreu, is a proven veteran and gives the Cubs solid production out of the 2-spot in the lineup. Bryant is a question mark for this series and Moncada is continuing his progression for the White Sox. 

Second base, which was a question mark for the Cubs entering this season, has been a bright spot with Jason Kipnis and Nico Hoerner having been stellar for the Cubs. The White Sox were hoping top prospect Nick Madrigal would step into the second base stop and run with it, but he went down with an injury and had to turn to Danny Mendick and Leury García to fill in the role. 

OUTFIELD

Andracki: In a year or two, it might be harder to pick the Cubs, but for this weekend – and 2020 overall – the North Siders have the better outfield. Luis Robert is only a month into his MLB career and has shown his tantalizing potential nearly every game and Eloy Jiménez continues to smack homers, albeit with little patience at the plate and questionable defense in left field. In right field, Nomar Mazara has been getting on base, but isn’t lending much slug to that lineup.

For the Cubs, Ian Happ has emerged as a bonafide star while Jason Heyward is having his best offensive season yet in Chicago. Kyle Schwarber is off to a bit of a slow start offensively, but I’d still take this Cubs outfield over the White Sox, even with Robert’s emergence.

Martinez: Jiménez and Robert are without a doubt exciting and seemingly have high ceilings. But at the moment, it’s hard to go against the trio of Happ (who has been performing at an incredibly high-level), Schwarber (who is hitting well) and Heyward, who is turning the corner offensively and plays right field at a Gold Glove level. 

Like Tony, in a year or two, this decision might be different, but at the moment, the Cubs have the edge. The Cubs have had an .896 OPS from their outfielders, compared to the White Sox output of .754.

STARTING ROTATION

Pitching probables for the weekend:

Friday – Jon Lester vs. Dallas Keuchel

Saturday – Kyle Hendricks vs. TBD

Sunday – Yu Darvish vs. Dylan Cease

Andracki: This is going to be a fun weekend to watch with the pitching matchups. Lester vs. Keuchel is lining up to be a great battle of savvy southpaws and Sunday’s finale promises some nasty movement between Darvish and Cease. 

The Cubs have the better rotation overall, even without former South Sider José Quintana (who is still working his way back from a thumb injury). That’s especially true this weekend, as the North Siders throw their trio of aces at the Sox.

Martinez: Lester vs. Keuchel should produce a very fine pitching duel. Now that both of us have pumped up the pitching matchup, the journalist jinx should provide a high-scoring game. But, on paper, Lester and Keuchel should attack hitters and produce a pitchers’ duel. 

Hendricks has been stellar all year and Darvish has been performing at a Cy Young Award level. This is the one spot on the rosters where the Cubs seem to have a clear, cut advantage and the White Sox will go straight into the lion’s den, facing the Cubs’ best three starters. 

BULLPEN

Andracki: The Cubs bullpen has been settling in lately but at the moment, the edge goes to the Sox here, as they’ve pitched well overall. Ross Detwiler (0.00 ERA, 0.35 WHIP) has reinvented himself as a reliever while Aaron Bummer is one of the most underrated relievers in baseball. Alex Colomé is steady as the closer and the Sox have received a boost from others along the way (Evan Marshall, Codi Heuer). 

One thing working in the Cubs’ favor here is they get Thursday’s off-day to rest all of their top relievers after playing 11 games in 9 days.

Martinez: Two or three weeks ago, heck even a week ago, the clear-cut upper hand would have been with the White Sox. Since then, though, the Cubs bullpen continues to find its groove and mojo. Ryan Tepera has proved himself as a dependable arm, Jeremy Jeffress is quickly becoming the ace of the bullpen and Craig Kimbrel is seemingly finding his old form. As he has reemerged, the bullpen has emerged, too. 

Bummer is quickly becoming one of the dominant lefties in the league and has a staggering 14.7 strikeouts per 9 innings. Colomé and Detwiler, coupled with Bummer, are showcasing the White Sox have the bullpen to contend in late September and in a potential postseason run. 

It’s a slight edge, but the White Sox take the edge. But check back back in a week, because the Cubs bullpen might’ve improved by then, too. 

DEPTH/INTANGIBLES

Andracki: The 2020 White Sox seem a bit like the 2015 Cubs to me. They’re a young and hungry bunch who brought in some proven veterans over the winter to help steer the ship toward contention. With 16 teams now in the postseason, I would be shocked if the Sox were not one of those, though I’m not sure they’ve yet ascended to the status of the game’s top teams. 

The Cubs have veteran leadership and are all pulling on the same rope this year as the David Ross Effect seems very much real and impactful for this team. 

The Cubs also have a bit more depth on their roster, but that has been tested this week with Bryant’s wrist injury, Tyler Chatwood’s back and Steven Souza Jr. now on the IL.

Martinez: The Cubs are fun. Whether it’s pumping it up and clapping when Rizzo or anyone else comes to the plate or having fun — socially distant — celebrations after wins, they’re playing with a swagger to them. They’re loose and playing good baseball, that’s a good combination for any team. 

The White Sox have been a bit of a roller coaster. They’ve gone on winning streaks with good moments (see: back-to-back-to-back-to-back home runs), but they’ve also shown moments of worry with losing streaks and Keuchel calling the team out. If they can put it all together, they’re a very, very dangerous team in the AL Central. 

FINAL VERDICT

Andracki: To me, the Cubs still feel like the big brother in the Crosstown Series, though that won’t necessarily always translate in head-to-head competition. With the North Siders throwing their three best starters and getting a much-needed day off Thursday to catch their breath after a wild stretch, I expect to see a fresh Cubs team claim the series victory at home over the weekend.

Martinez: The Cubs are still the favorites and on top of the proverbial hill. In a 3-game series, though, that doesn’t matter, as we’ve seen this season. The Cubs take the slight advantage this week, just because they are throwing their three best starters this series. It’s shaping up to be a fun series. With no fans inside the ballpark, it’ll be interesting to see the atmosphere on the rooftops. At the very least, we can expect some added energy when Rizzo comes up to bat in the 1st inning on Friday.