We’ve already looked at the Manny Machado trade from the perspective of the Orioles, who are shopping him pretty aggressively compared to what many people expected them to do heading into this offseason.
The White Sox are reportedly the most aggressive team in Manny Machado talks
Could they get him to flip him?


Right now, it looks like he’s going somewhere else before Opening Day, but it could also be that the Orioles take all these offers back to their Trade Cave and decide that they’re fine holding on to him for a few months of the season then see how their year goes before moving him.
The rumor
The current rumor comes from Ken Rosenthal of The Athletic, as many of them do during Winter Meetings, and it’s that the White Sox are currently the team most aggressively pursuing Machado as a trade target.
Why it makes sense for the White Sox
First, let’s clarify that the rumor in question could indeed mean that the White Sox are at the forefront in pursuing Machado, but it could also mean that right now they just have the best offer on the table. It’s all in the phrasing and which side, exactly, is leaking things from these discussions.
This would work for the White Sox though, and there are a few possibilities as to why. One is that they could acquire Machado for a few prospects and then flip him to the Yankees for a much better return than they gave up for him in the first place in order to continue their rebuild.
It’s like when a bar limits its massive specialty drinks to one per person, you get around it by having the designated driver order an extra one for you and hand it over. You only realize that’s a bad decision later on when everyone is mad at you, which is what would happen if Chicago hands Machado to New York after Orioles ownership specifically said it wouldn’t trade him there. It would be maddening.
The other option is for them to keep him for the year, and get rid of their current shortstop, Tim Anderson. If you aren’t familiar with Anderson, that’s a fine state to find yourself in. They could trade Anderson, who is signed through 2022 on a six-year, $25 million deal, and put Machado at short like he wants. Then they could either try to sign him long term or get a draft pick in compensation when he leaves.
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Why it makes sense for the Orioles
It’s because the White Sox have the prospects to make it happen. The Phillies have the assets to give the Orioles a good return for Machado, but right now it looks like they are reticent to give those up without a guarantee that they would get an exclusive chance to negotiate an extension with Machado as part of the trade agreement. Which probably isn’t happening.
If the White Sox don’t care as much about that, then they are a better trade partner that could offer the same level of return. The reason the Orioles are looking to trade Machado now (possibly) is for the return, so that’s what it is going to come down to.
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Rumor grade
C. This rumor, like others surrounding Machado, looks to have a time-sensitive nature to it. In another hour or seven, the Phillies could have the biggest trade package on the table, or the Cardinals could swoop in and take the lead as they’ve done in other situations.
There are so many offers heading the Orioles’ way for Machado that the action behind the scenes certainly seems unceasing right now. So while the White Sox could indeed be the current leader in negotiations, that could change in the blink of an eye.











