Dan’s Totally Informationally-Backed 2020 Free Agent Predictions

Dan Schmuldt
Nov 6 · 5 min read

Well, I’m sitting at Nashville International Airport awaiting my flight back to Chicago and while I have some time to kill, I figured I would take a crack at predicting where the top 5 free agents will land for the 2020 season and beyond. I say 5 now, but hell, depending on how I’m feeling I might do more. Let’s roll.

First off I would like to thank you all for asking how my trip was. I know you were all very curious when you read I was in Nashville for the weekend a couple of sentences ago. I’ve been here a few times, great town. Anyways, here are the guys I’ll be looking into:
Gerrit Cole
Anthony Rendon
Stephen Strasburg
Zack Wheeler
Madison Bumgarner

Okay, FINE. I’ll do a few short and quick ones too. Those will be:
J.D Martinez
Yasmani Grandal
Josh Donaldson
Nicholas Castellanos
Didi Gregorius

Without further ado, let’s jump into these 100%-confirmed, insider-approved, definitely-not-hot-take MLB free agent predictions.

Gerrit Cole:
Cole put up a huge season in 2019 (6.8 WAR, 20–5, 2.50, 0.895 WHIP) and added extra value to a HUGE payday with a pretty dazzling postseason performance. Just short of a World Series ring, Cole really came into his ultimate “first overall pick” form in Houston. Wether it be a change of scenery and a change to play for a real competitor or just the Astro Magic, (def a real thing) Cole is going to earn big time. If you read my blogs before, you’ll know I love WHIP and the fact that Cole not only posted a sub 1, but a sub .900, is incredibly impressive. No one hits the man, and the man walks no one.

As far as suitors go, I really like him out in LA with the Dodgers. Originally I thought an Astro reunion would be in the works, but after a pretty sour ending in 2019 when he wasn’t used to lock down the final 8 outs of the World Series, Cole might be looking for big bucks elsewhere. Houston has a plethora of big deals coming their way with their core of Altuve, Bregman, and Springer becoming arbitration and free agent-ready. Cole is from LA and the Dodgers are going to be able to spend big time without landing either Harper or Machado last Winter. Coming off of a pretty disappointing postseason run and watching a declining Clayton Kershaw, the Dodgers may have their 1–2 set for many years to come with Cole.

Anthony Rendon:

Rendon made a huge case for himself in 2019, and again on the biggest stage in the 2019 playoffs. Slashing .319/.412/.598, Redon posted an OPS over 1.000, and showed that his ability to come up clutch is second to none. While I really liked the Nationals to begin with, their commitments may lie elsewhere with Stephen Strasburg’s choice to opt-out.

While Washington does seem way more interested in bringing back Rendon than they did Harper, I think we’ll see Rendon elsewhere, and possibly somewhere that isn’t even a contender. With a new stadium opening in 2020 that will likely drive ticket sales, I think Rendon will move closer to his Texas roots and sign with the Rangers. Texas has made some small steps forward every year and looked pretty solid in the first half of 2019. Mix that with some smaller pick-ups and the Rangers may have something cooking for 2020 in beyond in the West.

Stephen Strasburg
The World Series MVP is coming off of a career year where he pitched some of the best baseball of his life. 18–6 with a 3.32 ERA, 251 Ks in 251 IP and a WHIP just over one, Strasburg opted out of his additional four years with the Nationals, but I don’t have him going anywhere. Winning the Nats their first World Series in franchise history after pretty much being the franchise since he came up, I got a feeling the Nats will pay Strasburg just about anything to keep him in the nation’s capital until he’s done pitching in the bigs.

Zack Wheeler:
Wheeler is a pretty solid 3–4 guy for just about any club looking to add an above average starter to their rotation. Pitching to a tune of 11–8 with an ERA just below 4 and a WHIP around 1.2, Wheeler won’t command big money, but will be able to pick from his suitors.

Up front I think anyone on the edge of or in contention will be looking into Wheeler so teams like the Mets, Nats, Braves, Cubs, Angels, Yankees and Twins could be a solid fit. With Joe Maddon coming aboard and a some jobs on the line in 2020, I think the Angels are really going to make a run at some starting pitching to give the club some legs for a full season in 2020. I like this for Wheeler. Don’t rule out the Yankees though, as they’ve needed SP since last year.

Madison Bumgarner:

After trade rumors swirled around him all off season and near the trade deadline, MadBum has finally hit free agency. Bumgarner is a workhorse SP, but had a bit of a down year in his walk year. Going just 9–9 with a WHIP sitting near 1.1 and an ERA at 3.90.

Despite a less than stellar showing, Bumgarner is still a champion in his core, and can pitch like one for any team in contention. His services will be sought after, but at the end of the day I have the Yankees coming out on top with a 3–4 year deal for the big lefty. Their future suits his pedigree well, and if the career Giant doesn’t come to terms with San Francisco, I wouldn’t be surprised to see him on his way to the Bronx to chase yet another ring.

Okay, time for some quick hits. I’ve been going too long here and I need some food here we go:

J.D. Martinez: Originally when writing this I liked the White Sox, but he’ll be staying Boston as he chose not to opt out of his deal with the Red Sox.

Yasmani Grandal: Shit, this one’s tough but I like him heading to a contender who lack a bit of catching. The Astros have my vote.

Josh Donaldson: I think if he chooses not to sign back with Atlanta, and the Cubs make some real moves and deal away Bryant he could end up in Chicago. That’s it. That’s the tweet.

Nicholas Castellanos: My favorite player to watch in 2019, I think Castellanos stays in Chicago with the Cubs for the next 4–5 seasons.

Didi Gregorius: Mets. That’s all I got there.


Follow me on Twitter @DanSchmuldt. I tweet about everything in the MLB, live Cubs updates, and anything else pertaining to Chicago’s North Side team.

Dan Schmuldt

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Writer. Editor. Social Marketer. Baseball fan. Avid gamer. Follow me on twitter @danschmuldt

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