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5 Biggest Offseason Decisions The New York Yankees Need To Make

The New York Yankees are going to win the 2020 World Series and no one can tell me otherwise.

The American League is wide open next season. The Houston Astros are about to get the death penalty for becoming an Orwellian Surveillance State.

JD Martinez just opted into his stupid contract which means Boston is about to foolishly ship off their perennial MVP candidate, Mookie Betts, for scrap parts like Gordon Gekko purchasing BlueStar airlines.

[Insert joke about whatever team in the AL Central that’s supposed to be good next season]

The 2020 World Series is the Yankees to lose but in order to solidify their place at the top of the mountain, this organization has some important roster moves they need to think about.

Here are the 5 biggest offseason decisions the New York Yankees need to make:

1.Gio Urshela or Miguel Andujar?

miguel andujar

Gio Urshela will be the third baseman on opening day next season. He earned that right. My man hit .314 with 21 bombs and 74 RBIs last year.

He was one of the only consistently productive players on the team and that’s without even mentioning how astronomically better at defense he is than Miguel Andujar.

That being said, Andujar led the team in hitting in 2018. We cannot pretend like he didn’t outhit the NL MVP, Giancarlo Stanton. That happened. We were all there.

You don’t just turn that player into a bench guy. The obvious answer is to trade him which is easier said than done. Not sure how many teams are in a hurry to acquire a guy coming off season-ending shoulder surgery who has no idea how to field a ground ball.

We’ll get to other positions later but it’s not impossible to move him to first base or throw him in the outfield. He’s young enough to learn a new position. There’s also a DH position available. Whatever you do to give him 3 at-bats a night.

But third base belongs to Gio Urshela.

2. Do you give Gerrit Cole whatever he wants?

This should probably be a no-brainer. Outside of Jacob deGrom, Gerrit Cole is the most valuable pitcher in baseball. If he asks for stock in the Yankees you start divvying up shares to Mr. Cole.

But nothing in the Yankees recent history should make you believe that they are willing to give Cole whatever he wants.

They desperately needed Dallas Keuchel last season and they lowballed him. The Astros signed him and they went to the playoffs. They lowballed Patrick Corbin last season. The Nats signed him and won the World Series.

Brian Cashman does not—and has never—valued starting pitching. The Yankees could lose in the ALCS every year and Cashman will shrug and say ‘welp, we tried our bestest. I’m going on vacation’.

3. Who’s on first?

luke voit

I have no reason to believe that Luke Voit is walking into Spring Training as the starting first baseman of the 2020 New York Yankees. Kid couldn’t even make the postseason roster over Tyler Wade.

But Luke Voit isn’t trash. re-read that sentence. That’s not necessarily praise. BUT, Voit had a 42-game on-base streak last season. He was in the top 10 of wRC+ before suffering a hernia in London.

It’s highly probable that Voit shows up healthy as hell and returns to smashing doubles and snapchatting ‘u up?’ to 12 different girls at 1 am.

There aren’t any real free agent options at first base. Maybe Justin Smoak but is that really a huge upgrade? Seems like a waste of money when Voit is set to make around $600k.

And let’s not forget that Greg Bird is playing winter ball in a third world nation right now ready to comeback with super strength and a mullet like when Superman returned after Doomsday murked him.

4. Is Jordan Montgomery ready?

new york yankees

I’ve already mentioned Cashman’s insistence that starting pitching doesn’t matter as much as having a roster full of designated hitters but someone has to pitch all of these innings.

A young man, Masahiro Tanaka is not. CC Sabathia is gone. JA Happ shouldn’t be on a Major League roster. Luis Severino and James Paxton is very much still around but this starting rotation needs depth.

You cannot run your bullpen out there to start every fifth day. It doesn’t matter how strong your bullpen is when they’re required to pitch every single day. There’s no way those arms make it into October.

Jordan Montgomery hit the ground running in 2017 starting 29 games and finishing with a solid 3.88 ERA. Then after just 6 starts in 2018, his elbow exploded and he is only now returning from Tommy John Surgery.

If/when Cashman offers Gerrit Cole $4 a year and Cole turns it down, Montgomery will be key.

5. Clint Frazier Time?

clint frazier jacoby ellsbury, new york yankees

Alright, enough playing around with this mentally frail child. It’s time for the Yankees to commit to Clint Frazier or trade his needy ass. We have no idea who Cashman is targeting yet somehow the first and only story coming out of this Yankees offseason is that they’ve already been in talks to bring back Brett Gardner.


I’m not a Clint Frazier fan. I think he’s an overly sensitive weirdo who stinks defensively and has done absolutely nothing on a baseball field to warrant the amount of attention he believes his ‘cool’ cleats deserve.

Frazier hit 12 homers and 38 RBIs in 69 games (nice). He clearly has a bat that is better than a AAA player. The New York Yankees need to decide who will be playing left field this season.

Regardless of what they decide, the 2020 New York Yankees probably won’t have to worry about Houston stealing their signs ever again.

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Written by TheLesterLee

Created Deadseriousness after being fired from every job I've ever had. One faithful night I drew the conclusion that if I was going to be unemployed, I might as well write articles that will guarantee I am un-hireable going forward. This website is the equivalent to a face tattoo.

E-mail to talk directly about all Deadseriousness related stuff or if you just want to talk about like, the Yankees or Marvel comics or whatever.

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