Outside of the four times they play every summer, the White Sox and the Cubs don’t usually pair up for very much. The two teams have only made a crosstown trade 23 times since 1946, but only once in the last 11 years. 

There are certainly a few that stick out. The Cubs trading Ron Santo in 1973 for Steve Stone, Ken Frailing and Steve Swisher. The Sox trading a guy named Sammy Sosa for George Bell in 1992. And then there’s the Cubs dealing future World Series champion Jon Garland to the Sox in 1998 for Matt Karchner. 

Those are definitely some interesting trades, but I wouldn’t call any of them blockbuster deals. 

Through one month of the 2017 season, with the Sox in the first steps of a long rebuild and the Cubs trying to repeat as World Series champions, there is already chatter of a potential Sox-Cubs trade on the horizon. And it all hinges around pitcher Jose Quintana. 

It has seemed like a foregone conclusion that the White Sox will move Quintana at some point this season. Rick has been adamant that he’s going to wait for an equitable deal that gives the Sox a sizeable return for what they consider an ace pitcher. Quintana is talented and cost-controlled, so plenty of teams in need of pitching are sure to come calling around the deadline. But could a deal come sooner, and closer to home? 

The Cubs have gotten off to a slow start to the 2017 season. Although any overreaction from Northsiders is incredibly premature, it’s apparent that the World Series honeymoon is pretty much over. 

The Cubs need help with their starting pitching. The Sox have Jose Quintana. The Sox need more offense in the system. The Cubs have some really good hitting prospects. 

It’s a match made in hell. 

The two teams’ needs definitely line up well. The problem is, in my opinion, a mismatch in asking price. You’d have to assume Rick would initially ask for a league-ready guy like Baez or Schwarber as a headliner. But I think Theo nixes that offer right away. I don’t think the Cubs are eager to deal any of this current core, especially to the White Sox. So if that isn’t an option, what does Rick Hahn do? Does he absolutely have to get an MLB-ready guy in return for Q? Or is a haul of top prospects an acceptable return at this point? I’m not sure. 

I played “Sox-Cubs trade machine” earlier and landed on this: two of Happ, Jimenez, Candelario plus one or two additional fringe prospects would be good enough for me to send Quintana to the Northside of Chicago. I’d personally take Jimenez over Happ at this point. The White Sox have a huge need in the outfield, and won’t have a need at 2B for much longer. Jimenez would fill the need in the OF, and Candelario would fit a need at the plate and at third as well. 

With a deal like that the Sox would get two great offensive prospects (two of the top three in the Cubs’ system), and the Cubs would shore up their starting pitching with controlled cost for the next few years. 

But it’s important to remember that the Cubs aren’t the only option the White Sox have here. Teams like the Yankees, Astros and Rockies have pieces (some would argue better pieces) that could make a deal work. Rick has also been very open about how the Sox are gonna let this come to them and not jump the gun on a Quintana trade. Of course there’s some risk to that, but it’s also the smartest course they can possibly take. The Sox hold all the cards.

I’m also skeptical about how much the Cubs are really concerned about their starting pitching. You’d think Theo could probably fix the problem in-house and not have to make a trade. Also, that lineup is too good to be slumping like this for the whole season. The World Series hangover is real, but to think the Cubs can’t turn it on and win with this roster in 2017 is foolish. 

The one thing we haven’t addressed yet is the stigma that would come with a crosstown trade. There’s obviously no love lost between these two fanbases. Make no mistake, any trade between the teams would be huge news. Everyone and their mother would have a take on it, good or bad. 

When it came out this winter that the Sox weren’t interested in dealing Chris Sale to the Cubs, the wide response chided them as being bitter and dumb. Fast forward to right now, where Rick Hahn has been very open about… being open to dealing with the Cubs this time around. Barstool Chicago’s Dave Williams (whitesoxdave) gave his take on the Quintana trade frenzy, saying that the notion that Hahn wouldn’t deal with the Cubs is B.S. 

Comparing a Sale deal to the Cubs with a Quintana deal to the Cubs is like comparing apples and oranges. The optics are different. Dealing the face of the franchise (Sale) to your direct competition for eyeballs, the Cubs, right after their World Series frenzy would have been a terrible look for the Sox. It definitely plays right into the White Sox inferiority complex, but it’s also very true. They would have gotten a haul of a return (which they did anyways), but at the same time it would have looked like further conceding a piece of the pie.

It’s now a whole different ballgame with Quintana. He’s not the face of the franchise, the Sox have already chosen their lane, they won’t be aiding the Cubs efforts to break the “curse,” and back in the winter the Cubs’ need for starting piching wasn’t as high as it is now. They’re suddenly a really viable trade partner. 

But you also have to wonder if the pendulum has swung the other way. Does Theo want to deal with the Sox at all? What are the optics of sending two of your top three prospects across town to the White Sox? Could that come back to bite the Cubs down the road? Does Theo even care about optics if he can make his team better and win more championships? Who knows. 

The only known here is that Quintana is a great cost-controlled pitcher who could definitely help the Cubs, and the return for him would also greatly help the White Sox as they get this rebuild off the ground. But history tells us to not hold our breath waiting for a crosstown deal.