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Sporcle Saturday: The richest free agent deals in White Sox history

Show me the money!

Albert Belle

Unless you’ve been away from the internet the last few days, you’ve no doubt heard the rumors swirling about regarding a possible trade between the Orioles and the White Sox involving superstar Manny Machado. This seems unlikely to happen, but even if it did, it will likely be just a one-year rental. With some of the largest free agent deals in MLB history likely to occur next offseason, Machado’s best interest is to test the waters and eschew an extension, barring something beyond formidable.

With that said, let’s forget about Machado, take a step back and use today as an opportunity to review some of the White Sox’ largest free agent signings in franchise history. Your assignment, should you choose to accept it: name the players who have received the largest free agent contracts from the White Sox (at least 4 million dollars) AND have reached the major leagues (for the Sox or another team). That’s 32 names in all. Good luck!

A couple of notes before we get started:

  • This includes free agent signings only. No extensions, so pacts like Mark Buehrle’s extension are off the table.
  • There’s no single best place to obtain free agent signings for a team that I could find: MLB Trade Rumors has a great transaction page, but it only goes back to 2006. Likewise for Cot’s (2009), and while Baseball Reference has good salary data, it doesn’t make it easy to tell when there was a player/club option, any extensions that occurred to bump up the salary, and so forth. Therefore, I had to compile this list by hand, double-checking some of the older signings from Newspaper Archive and Historic New York Times. If I missed anybody, let me know down in the comments and I’ll add them to the list.

Quiz Parameters

  • As always, last names are accepted, in addition to both first and last.
  • You’ll have ten minutes to attempt completion.
  • For hints, I’ve provided the date of the signing and the contract value.

Data from a combination of Baseball Reference, MLB Trade Rumors Transaction Tracker, the New York Times archive, and

Direct link here