Sox Machine 2019/20 Free Agent Pick’em Contest

Tonight is Game Seven of the 2019 World Series, and MLB Free Agency will begin five days starting tomorrow. During those five days, we will hear updates across the league in which contract options will be picked up or who will be released.

Just like last year, we will be having a Free Agent Pick’em contest. Just pick which team you think free agents will sign with for a chance to win (2) tickets to the White Sox vs. Royals game on March 28, 2020 (Opening Weekend). The tiebreaker is guessing how much Gerrit Cole and Anthony Rendon combined contracts will be. Bookmark this page to revisit the leader board standings to check how you’re faring against the competition.

Pick’em Standings

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Josh Nelson
Josh Nelson

Josh Nelson is the host and producer of the Sox Machine Podcast. For show suggestions, guest appearances, and sponsorship opportunities, you can reach him via email at

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What’s the deadline – the end of the 5-day window?

I always do embarrassingly bad at these free-agent contests, but nonetheless I will submit a form for your amusement.


Got busy and missed the deadline. Oh well.


That was fun, thanks Josh. Good luck Sox fans!




Too late to get in the contest, but here are my not-so-carefully-thought-out picks anyway.

Cole – Angels
Rendon – Rangers
Strasburg – Nats
Wheeler – White Sox
Chapman – Yankees
Martinez – Red Sox
Bumgarner – Twins
Grandal – White Sox
Donaldson – Nats
Ryu – Dodgers
Castellanos – Cubs
Ozuna – Reds
Gregorius – Twins
Odorizzi – Twins
Keuchel – Angels
Smith – Twins
Moustakos – Braves
Hamels – Braves
Puig – A’s
Garcia – Giants

The combined contracts of Cole and Rendon – $495M