First of all, there’s a reason this is the boldest prediction of the offseason because there’s close to zero percent chance of it actually happening. I mean, look how this is framed by MLB.com’s Anthony Castrovince, who made this list of bold offseason predictions.

Because baseball/people/the world will surprise you, I find it important to throw out one truly bonkers prediction. If I’m wrong, at least it’s not the first time, and the world will move on. If I’m right, I will be heralded as a clairvoyant. Or in this case, a Colevoyant.

Mainly just sharing this because it’s fun, so stop complaining. I also wanted to point out some of Castrovince’s reasons that don’t really match up when it comes to why Gerrit Cole could end up signing with the White Sox. Again, there’s a reason why this is the boldest prediction of the offseason.

So, Cole to the White Sox? Via MLB.com.

“But Cole wants to pitch for a West Coast team!” you cry.
We said the same thing about CC Sabathia before he signed with the Yankees.
“But the White Sox aren’t contenders yet and have never given a contract this size!” you reply.
Eh, we said basically the same thing about the Padres before they signed Manny Machado.
This is going to be a financial decision, not a sentimental one — or couldn’t you tell when Cole threw on that Boras Corp. hat like 20 minutes after the World Series ended? While I know the Second City isn’t Cole’s first preference and I’m well aware that the White Sox have avoided deals of this magnitude, they
have the makings of an American League Central contender and have less than $20 million in salary commitments in each of the next five seasons. This would be like when the Cubs signed Jon Lester prior to the 2015 season and brought further legitimacy to a team on the verge of becoming a real title threat.
I figure there’s about a 1.6 percent chance of this happening … the same percent chance the Nats were given of winning the World Series when they were 19-31!

The premise isn’t wrong. The White Sox, with a few big additions this offseason, should be ready to compete in a weak AL Central and top-heavy American League. They have a whole bunch of money available before they even sniff the luxury tax, which MLB owners could not be more scared of.

So it makes sense. The White Sox need a starting pitcher to fortify their rotation, have money to spend and one of the best free agent starters in the past decade is available.

HOWEVA! We’re talking about Jerry Reinsdorf’s White Sox.

Hmmm, I wonder why CC Sabathia signed with the Yankees despite preferring to go out West? Maybe it was because the Yankees offered him a seven-year deal, worth $161 million, the biggest contract for a pitcher in MLB history at the time.

The point about people being surprised at the Padres signing Manny Machado to a $300 million contract because they had never signed a huge deal before just isn’t true. In 2018, the Padres signed Eric Hosmer to an eight-year, $144 million deal. And although it wasn’t a nine-figure contract, in 2015 the Padres signed James Shields to a $75 million deal over four years. The closest the White Sox have had to a big free agent signing was Jose Abreu’s six-year, $68 million contract.

So yes, this is going to come down to money and here is a reminder of the richest free agent contracts the White Sox have ever agreed to.

The biggest free agent deal for a pitcher was in December 2014, when the White Sox signed closer David Robertson to a four-year, $46 million contract. The biggest free agent starting pitcher the White Sox have ever signed was Jaime Navarro in December 1996, a four-year contract worth $20 million.

The White Sox were in on Machado all the way to the end last offseason, but they felt content offering him less money than the Padres and saw him sign in San Diego.

Gerrit Cole is projected to get close to $250 million this offseason.

So yeah, it would be quite the bold move if the White Sox actually stepped up and signed the number one free agent this offseason when they have never shown to go above and beyond in free agency.