Does a Manny Machado trade to the White Sox make sense?

The White Sox are reportedly interested in Manny Machado. (AP Photo/Gail Burton)
The White Sox are reportedly interested in Manny Machado. (AP Photo/Gail Burton)

The 2017 Winter Meetings were mostly a bust, but at least fans got a taste of one completely bonkers trade rumor before they were over. Turns out, the most aggressive suitor for Baltimore Orioles third baseman Manny Machado is the … Chicago White Sox?

Ken Rosenthal of The Athletic reported that the White Sox have emerged as the “most aggressive suitor” for Machado. Shortly after his article, other reporters confirmed Chicago was in the running for the star third baseman.

The news was met with collective shock from the baseball world. Despite vast improvements to their farm system, the White Sox are thought to be a couple years away from contention. While Machado is a superstar caliber player, the 25-year-old is slated to be a free-agent at the end of the 2018 season.

The move doesn’t make sense. Why would the White Sox give up members of their farm system for a guy who won’t be around when they are ready to win? While Machado is great, he couldn’t carry a team slated to start Charlie Tilson, Leury Garcia, Nicky Delmonico and Dylan Covey to the postseason. Optimistically, he helps the team get to 78 wins and then leaves for a massive free-agent deal.

But that won’t stop people from trying to make sense of the rumor. Thus far, two narratives have emerged: Either the White Sox want Machado now because they believe they can get him to agree to an extension, or they want him so they can flip him to another team in a more lucrative deal.

Both scenarios require you to bend logic in order to buy in. The idea of the White Sox convincing Machado to sign a giant extension just months before he hits free agency is highly unlikely.

There are plenty of reasons for this. Players who hit free agency tend to get paid more than players who agree to extensions. It’s easy to figure out why that’s the case. Players are more likely to receive more money when 30 teams are bidding against each other, as opposed to limiting the bidding to just one club.

Let’s say Machado just loves Chicago and completely buys into the team’s future. Even then, players like him don’t pass on free agency. Since 2012, there’s only been one player who signed an extension over $60 million with a new club as free agency approached: Rick Porcello. He agreed to a four-year, $82.5 million extension with the Boston Red Sox in 2015 after being traded to the club in the winter.

The optimist might look at that as a reason this could work, but keep in mind Porcello ain’t Machado. Before signing his extension with Boston, Porcello was a below-average pitcher throughout his career. His ERA+ from 2009 to 2014 was just 97 — three percent below the league-average. Machado might be coming off a down year, but he’s still a top-15 player in baseball. He’ll make three times as much as Porcello next winter.

There’s also a question of whether the White Sox would even spend the money. Despite playing in Chicago, the White Sox are one of a handful of teams to have never handed out a contract in excess of $100 million. They’ve shown a willingness to take on questionable deals in trades, and even ran a decent payroll at times during the mid-2000s, but have never made a huge splash on the market. It’s possible they are willing to finally do that now, but the lack of track record is another thing working against them with Machado. After never exceeding $100 million, are they suddenly going to hand out a $300 million deal?

That makes the second option — trading for Machado so you can flip him to another team in a better deal — more believable. The New York Yankees are said to be interested, and still have a strong farm system, but the Orioles may hesitate to deal Machado to a division-rival. Perhaps the White Sox could swoop in, help New York and somehow come out richer.

That type of trade would require meticulous planning, behind-the-back negotiations and assurances that everything would go perfectly. It’s a galaxy brain-level deal — a plan so convoluted you’d expect it to come from a Bond villain. It’s also the type of deal that happens in fantasy leagues, not in the major leagues.

That’s the common theme here. In order for this move to make sense, the White Sox would have to have another trick up their sleeve. And while that’s not impossible, it’s highly unlikely considering all the factors.

You can daydream about a perfect scenario where Machado becomes another key clog in the White Sox’s rebuilding effort. But at a certain point, logic has to win out.

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Chris Cwik is a writer for Yahoo Sports. Have a tip? Email him at or follow him on Twitter! Follow @Chris_Cwik