We’re t-minus 23 days and counting until the trade deadline with little activity other than speculation and rumors — much of which are surrounding White Sox pitcher Jose Quintana. The latest scuttlebutt has Milwaukee jumping into the mix for the 28-year old lefty’s services.

A deal between the last place Sox and  first-place Brewers makes a lot of sense on many levels. Despite his mediocre 4.45 ERA and 1.32 WHIP this season, Quintana’s extremely team-friendly contract makes him attractive to any ball club, but especially for a smaller market like Milwaukee who may have a brief opportunity to capitalize on a what has been a surprising down year for their NL Central division rival Chicago Cubs.

The White Sox would undoubtedly covet some of the top prospects in the Brewers’ consensus top-5 farm system, but would also delight in the chance to spite their crosstown rivals—the aforementioned Cubs.

Infamous for his blind hatred of the North Siders, it’s not hard to picture White Sox owner Jerry Reinsdorf  laughing maniacally as he signs off on a deal that helps stick it to the defending World Champs. Even more telling of the organization’s irrational disdain for a team they face only four times a year is the reported insanely high asking price GM Rick Hahn gave Cubs President Theo Epstein when inquiring about Chris Sale last year.  While they would otherwise be an obvious match to be trade partners, talks were about as brief as it gets between the two because of Hahn’s outrageous demands:

“We had a really quick conversation about Sale,” Epstein told The Score’s Mully & Hanley Show. “It lasted about 30 seconds based on some of the names involved that he would want. And not prospects, but big league players.”

While Hahn publicly denies dealing with the Cubs any differently than the other 28 MLB franchises, his actions say otherwise. The fact that the return for Sale he eventually obtained from the Red Sox included only prospects and no big leaguers speaks volumes. With Sale under contract until 2019 in a similarly team-friendly deal, Hahn wasn’t in a a position to have to settle for anything. Acquiring top prospects was always his only goal and he achieved that. Cleary, his demands from the Cubs were purposely ludicrous so that deal—and potentially any future deal—could never be possible. It’s a shame too, because a reasonable deal for Quintana could help both clubs immensely.  But the Sox’ illogical fear of doing anything that might be perceived as helping the Cubs is obviously a factor despite going against their own self-interest.

So with the Cubs eliminated as a potential trade partner yet at the forefront of the Sox paranoid collective mind, if a Quintana to the Brewers deal does actually materialize, Sox fans shouldn’t be too surprised if the return is a bit underwhelming. The difference will be made up for in spiting the Cubs. Hope that helps you all sleep at night.