The Chicago White Sox might get another chance at Manny Machado in 2023

Championship Series - San Diego Padres v Philadelphia Phillies - Game Four
Championship Series - San Diego Padres v Philadelphia Phillies - Game Four / Matt Thomas/San Diego Padres/GettyImages

We all remember the 2018-19 offseason that had one of the craziest free-agent frenzies of all time. The Chicago White Sox were heavily involved and came up short when it came to all of thier goals. They are still feeling the effects of it here in 2022-23.

The thing that made that off-season so unique is the fact that there were two mega free agents at the age of 25. There are big free agents all the time but none of them are ever that young. Bryce Harper ended up going to the Philadelphia Phillies and Manny Machado ended up with the San Diego Padres.

As mentioned before, the White Sox were in on both but they were clearly way more interested in Machado as he fit a big need for them. They also signed Jon Jay and Yonder Alonso who are close with Machado. That technique failed for them as Machado hit the west coast.

It looked like it wasn't that big of a deal for a while but it is clear that it set the White Sox back. They were willing to hand out all this money for the first time ever but it never came to light. Now, it would be really nice to have one of them.

The Chicago White Sox missed on the biggest free agents in 2019.

Both Machado and Harper have made deep playoff runs with their teams. They have both been in MVP conversations. Both have been incredible signings that neither team would take back if they could. It is rare that free-agency works out this well. Neither has won the World Series yet but they are close.

On Friday, however, we learned that Manny Machado might be on the market again soon. According to Jon Heyman of the New York Post, the San Diego Padres anticipate that Machado will opt out of his contract following the 2023 season.

That would send shockwaves across the entire league as all 30 teams would try to get him. He is too good to pass up. Of course, getting him at 30 will be a lot different than at 25 but we just saw what Aaron Judge just got at roughly the same age.

The White Sox should be all over this. Some big money is coming off the books after this year and this might be their chance. Alonso and Jay are both out of the picture now but it would be nice to still see them go for something like this.

We don't know how this season is going to go for the White Sox but landing Machado after it would be a lot of fun. The fact that we are having this conversation is really interesting. You just never know.

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