I’m the classic big-headed Chicagoan, aren’t I? Yes, I am fully aware Illinois has had way more governors thrown in prison than World Series titles in the past century. I am aware that the city of Chicago consists one baseball team who refuses to spend money and another that apparently refuses to spend wisely.

But yet, at least until pitchers and catchers report in February, the Windy City is going to be the center of the baseball universe. And it starts with the team you would least expect.

The White Sox, and owner Jerry Reinsdorf, have been historically awful at spending money to improve their baseball team. Awful. The largest contract the White Sox have ever signed was a 6-year, $68 million contract with Cuban 1B Jose Abreu, one which he opted out of half way through. However, as I have discussed before, that’s about to change.

As he’s getting older, Jerry wants another ring. He approved an intelligent rebuild of both the Sox and the Chicago Bulls, something which seemed unfathomable just five years ago. Now, as the White Sox turn the corner and head towards the improvement part of their rebuild, they need a catalyst to start that process.

Reinsdorf and general manager Rick Hahn realize this. The White Sox are following the Cubs model, and they feel like this is their time to make their equivalent to the Jon Lester signing. They want a high impact superstar to be donning the black pinstripes and sometimes that awful uniform Chris Sale tried to cut up.

“No one should be surprised about seeing us involved with potential impact names that although given where we’re at right now in our rebuild, 2019 might not be the moment of greatest impact impact for all these players, we may be able to pick up some players via trade or free agency that align with what we’ve accumulated and make sense for us in the long term.” – general manager Rick Hahn (via NBC SPORTS CHICAGO)

While he clashes with the hustle-first mentality of manager Rick Renteria, Manny Machado is that guy. While Reinsdorf is willing to spend, I still have trouble believing that he is going to shell out the half a billion dollars I’m expecting Harper to get. Machado isn’t represented by Scott Boras, and that’s a massive part of the reason the Sox are going to be after Machado more aggressively than his outfield counterpart.

I wouldn’t put it past the Sox making a massive trade either. While they aren’t going to be trading top prospect Eloy Jimenez or top pitching prospect Michael Kopech, I wouldn’t be surprised to see the Sox deal some prospects for a huge name. Dylan Cease is going to be the next great pitcher, so he won’t be moved either, but I wouldn’t be shocked if the Sox part with Dane Dunning, Blake Rutherford, or Zach Collins if they get a big name guy.

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That “big-name guy” won’t be any of Cleveland’s pitchers, but very well could be a guy like James Paxton. The Sox need a big-name starter, and Paxton will be available for relatively cheap now that Seattle has initiated their fire sale. It would cost at least one of the aforementioned prospects, but in many ways, those guys are superfluous to the South Siders’ plan.

On the north side of town, it’s an unwelcomed change. All of the media speculation is that the Cubs, despite the riches they get from both TD Ameritrade and the money-printing machine that is the baseball organization, don’t want to spend big this offseason. We are yet to see if this is actually true, but if it is, it could lead to a lot more chaos.

The trio of Ian Happ, Albert Almora, and Kyle Schwarber will not be all be gracing the Wrigley Field outfields this year. I don’t see any scenario in which none of them is traded this offseason.

Cubs President of Baseball Operations Theo Epstein seemed fed up with his team’s lack of hitting during their abbreviated postseason run. I would be extremely surprised if the Cubs don’t make a big name trade, including at least one of their major league bats.

“It’s time to stop evaluating in terms of talent and start doing it in terms of production.” – Cubs President of baseball operations Theo epstein

The Cubs need a late-inning reliever, along with another consistent bat. While this is a lot easier said than done, the Cubs are going to be going hard after those kind of players this offseason. They may look in free agency, if their “crying poor” is just a ploy to get guys for cheaper, but we do not know whether or not that is the case.

If they do look for the trade route, just like the Sox, Seattle makes a lot of sense. It would cost a lot to make Seattle part with star closer Edwin Diaz, but the Cubs are going to look that route. Seattle would ask for a lot more than Ian Happ if they were to part with Diaz, but the Cubs have some highly regarded prospects such as C Miguel Amaya that could move the other way.

There are other teams looking to move big name relievers, such as the Diamondbacks with Archie Bradley and possibly the Reds with Raisel Iglesias, as well. As Epstein and company always do, expect the Cubs to cast a wide net, in both free agency and trades.

And that wide net is precisely why any business this offseason is running through Chicago. More than any other team in the league, the Cubs are going to be in on everyone. Quite literally every major trade chip. You are going to hear the Cubs name thrown around about almost everyone available, in any capacity, this offseason. Even the starting pitchers, where they don’t have a need.

Get ready for the grueling winter, baseball. You are headed through the bone-chilling winter in the Windy City.

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