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Here’s a fun game to help New York Yankees fans get through the boring part of the offseason and to Spring Training 2019.

Aaron Case

The New York Yankees’ first spring training game is 43 days away, which feels like an eternity at this point in the offseason. With the Bombers dragging their feet in free agency, all fans can do is wait for some action.

They’ll wait to see if Troy Tulowitzki will really be Didi Gregorius’s replacement. Wait to see if Gary Sanchez and Greg Bird can rebound from their horrific 2018 performances. Wait to see if the Yankees can overtake the Red Sox in the East.

All this waiting is like watching paint dry. It’s like a long, boring road trip.

I don’t know about you, but I need a distraction to keep from going insane. I’d like to play a little game of Bombers-style “Would You Rather.”


In case you’re not familiar with the game, here’s a quick rundown: you choose two terrible situations and then debate among your friends about which option is the most tolerable.

Let’s start with something lighthearted.

Would you rather wear this garish Yankees hat or this comically retro Bombers sweater?

I recently took a deep dive into Yankees news, and I came up with one of the most cringe-worthy pieces of apparel I’ve ever seen:

If the tacky bejeweling isn’t bad enough for you, just take a look at the $530 price tag. Call me uncultured, but this cap is the definition of garish.

Imagine a dude topping his head with this thing to take in a frosty October playoff game at Fenway Park. There’s no way that would end well.

The only person who can get away with wearing a hat like this is Yankees president Randy Levine. He recently found out he’s a descendant of French queen Marie Antoinette, so a jewel-encrusted Yankees crown almost makes sense for him.

Another bit of Bombers gear recently made the news. The TV series “Antique Roadshow” valued a sweater worn by Yankees first baseman Wally Pipp (played for the Bombers from 1915 to 1925) at $77,500:

I understand the historical significance is pretty cool. However, unless you want to look like Mr. Rogers after he let a toddler draw the Yankees’ interlocking NY in crayon on his chest, I’d recommend keeping this sweater on display.

So, here’s the question: if you could choose just one of these two pieces of Yankees garb to wear on every trip to the stadium, would you rather have Gucci’s abomination or Pipp’s outdated sweater?

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My answer is the Gucci hat because maybe I can rip off a few of the jewels and convince a stadium vendor to let me trade them for beers. The Pipp sweater’s value would probably drop by about $77,000 as soon as I put it on, which would leave me with an ugly sweater that wouldn’t even make sense at Christmas.

Would you rather sign Bryce Harper or Manny Machado?

Admittedly, that last bit was kind of silly. Don’t worry, though. This one and the next are all about baseball.

Deciding whether you’d rather have Manny Machado or Bryce Harper on your team is like holding your nose to vote in a lesser-of-two-evils situation.

Now, I’ve been beating this dead horse like it’s Floyd Mayweather Jr. versus Tenshin Nasukawa. Both guys have a history of selfish, childish behavior on the field.

From Machado throwing his bat into left field to Bryce Harper’s temper tantrums, there’s just too much unsightly behavior to ignore:

Sure, they’re young—both only 26 years old—and super talented. However, I can’t help but wonder if their career trajectories will play out like that of a typical Disney child star. Either one could get bored with all the success and money and then turn into the MLB version of Lindsay Lohan, going off the deep end in terms of productivity.

With that in mind—and with my nose held tight—my answer to this would-you-rather question is Manny Machado.

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Even after considering Harper’s lefty swing, crazy-high OBP even in off years, and 50-HR potential, I have to go with Machado’s consistency.

Harper hit below .250 twice in the last three years, and he’s missed more than 40 games in three of his seven seasons. Machado’s lowest games-played total in the past four years is 156, and he’s only hit less than .270 two times in his seven-year career.

Would you rather trade Sonny Gray but have Jacoby Ellsbury start in left field, or trade Ellsbury but have Gray start 30-plus games?

Sonny Gray and Jacoby Ellsbury are probably the two least-wanted players on the Bombers’ roster.

Gray as a Yankee is 15-16 with a 4.51 ERA and a 1.40 WHIP. Jacoby Ellsbury missed all of last year due to injury. I don’t think anyone missed his average of 7.66 homers the past three years in a stadium known for a short porch in his pull field.

Still, when it comes to choosing one as a full-time contributor, I have to go with Ellsbury, and I think my reasoning holds up.

The Yankees have an offense that can cover up a weak hitter; their rotation is far from the same.

CC Sabathia’s right knee, Masahiro Tanaka’s right elbow, and pretty much every part of James Paxton’s body are a few reasons. Luis Severino’s horrible ending to 2018 is another.

You might want to argue that Ellsbury’s high price tag makes Sonny Gray the better option. I would counter that an Ellsbury trade will return a similarly bad deal (see the Ellsbury for Robinson Cano rumor), so it’s really just about the impact on the field. Gray’s impact as the starting pitcher in 30-plus games could be extremely detrimental.

Let these three questions trigger your own game of Yankees-themed Would You Rather. By the time you’re done bickering about the questions you devise, you’ll have arrived at your destination: Spring Training 2019.

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