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Would You Rather? How winning a weird World Series could change each MLB contender's narrative

Hannah Keyser
·12-min read

Now that we are officially In The Thick Of Things with postseason baseball, there are enough dynamic plays and impactful decisions to unpack that it almost feels like this is all happening under normal circumstances. When you’re watching well-matched teams duke it out between the lines, the stakes and the motivations seem simple, one and the same: to win it all. The season at this point starts to look like a straightforward foot race to snag the championship, no baggage or bulls--- about asterisks.

Your team (or the team you hate) is so close to putting the weirdest summer behind it in a way that makes it look worth it. But to do so is to hurl themselves headlong into a whole new set of storylines! Winning doesn’t erase the narrative; if anything it cements it!

Right now, you — the fan, and also the team — think you know what you want above all else: a World Series title. But in this economy? Really? In an effort to not-quite-quantify but qualitatively evaluate how satisfying a 2020 championship would be to each team and fanbase, and for the sport at large, I present to you a series of Would You Rathers for the four remaining contenders. It won’t tell you anything about the game, but it might tell you a little something about yourself.

ARLINGTON, TEXAS - OCTOBER 07: Clayton Kershaw #22 of the Los Angeles Dodgers reacts as he walks to the dugout during the sixth inning against the San Diego Padres in Game Two of the National League Division Series at Globe Life Field on October 07, 2020 in Arlington, Texas. (Photo by Tom Pennington/Getty Images)
Is it worth risking another disappointment for Clayton Kershaw and the Dodgers core to try to break their World Series drought in a non-pandemic year? (Photo by Tom Pennington/Getty Images)

Los Angeles Dodgers

The Choice: If you are a Dodgers fan, would you rather guarantee that they win the World Series this year, but are cursed to not win again for at least five years, OR that they fail to win this year and forgo any guarantee at all, leaving it up to the consistently disappointing combination of talent and luck. In other words: Have the past seven years been so disheartening, so traumatizing that you’d take the sure thing even if it came in a shortened season?

The paradox here is that the current Dodgers are undoubtedly talented enough and deep enough to dominate in any regular season, to break the franchise’s drought in a normal World Series at home in front of the L.A. faithful — or at the very least, on the road in a full stadium after hosting part of the series. And that talent is sustainable enough — Mookie Betts is signed through 2032 — that fans can reasonably expect the team to be playing in many Octobers to come. They don’t need a fluke season to fall their way. If anything, winning a world championship in the same year that a team without a home stadium on opening day, one that didn’t even finish 60 games, and the Marlins all made the playoffs feels like an insufficient monument to what the Dodgers have built.

But, I don’t have to tell you that great Dodgers teams don’t alway lead to happy offseasons. If you’re my age, you’ve seen the Dodgers play in 13 Octobers and never gotten to go to a championship parade. I mean, I don’t know if you would get to go to one this year, but I bet they’d do a caravan or something like that. Clayton Kershaw has been good this year. He’s not getting any younger. Don’t you want this for him now? Can he handle another disappointment?

The Dodgers are proof that building a dominant team doesn’t guarantee you anything except that when it breaks your heart, you’ll be all the more blindsided. And every failed season puts you back at the starting line, along with 29 others, where something could go wrong. Careful if you start to think making it this far should be taken for granted.

But would one championship even be enough if it’s overshadowed by the pandemic and accompanied by the inevitable asterisk of a short season? Could you live with yourself knowing that they will play the next five seasons in vain? Would it help if you didn’t bother to get your hopes up?

Dodgers fans should take heart that the reason this hypothetical even works is because the team has dynasty potential. But not too much heart, because it’s reasonable to think they might mortgage the next half decade just to ensure they don’t go down in history as the best team to never bring it home.

My pick: I say you gamble without a guarantee. Another early exit or failure on the biggest stage would only heighten the pressure, but even that’ll be worth it if they ever break through in a non-pandemic year.

SAN DIEGO, CA - OCTOBER 09:  Randy Arozarena #56 of the Tampa Bay Rays takes a lead off first base during Game 5 of the ALDS between the New York Yankees and the Tampa Bay Rays at Petco Park on Friday, October 9, 2020 in San Diego, California. (Photo by Alex Trautwig/MLB Photos via Getty Images)
Upstarts like Randy Arozarena sometimes beat the Yankees' highly paid stars, but is it what you want to pin your hopes to every season? (Photo by Alex Trautwig/MLB Photos via Getty Images)

Tampa Bay Rays

The Choice: If you are a Rays fan, would you rather guarantee that your team wins the World Series this year, OR loses this year but starts spending like the Yankees next year?

This year, the Rays had the third-stingiest payroll in baseball. Their division rival Yankees had the largest, nearly four times as robust and full of name-brand stars. Stop me if you’ve heard this one before.

The Rays faced that disparity head-on all season — repeatedly, and ultimately dramatically, trouncing their rich neighbors to the north. Now they’re one win away from their second Fall Classic appearance, gunning for their first championship since the team’s inception as the Devil Rays in 1998.

It’s a pretty likable group of guys they’ve got going this year, too. I mean, how can you pass up a chance to secure an unprecedented World Series win for the likes of Tyler Glasnow, Randy Arozarena, Ji-Man Choi and Mike Brosseau?

Especially because I think some Rays fans (there only are some Rays fans, but stay with me) are protective of that chip on their shoulder.

The Rays’ reputation as crafty upstarts, perpetual underdogs, analytical darlings (turned anti-labor paradigms) is part of their hard-won identity. And they are good at making the most out of a little. Rooting for the suits to cut corners successfully is a strange sort of fandom from my perspective, but one that certainly exists. There’s pride in being the team that takes its shallow packets all the way to the top. Besides, if anyone is going to win a World Series this year, it might as well be the one that’s better loved on television than in person anyway.

On the other hand, don’t get too attached to any of the undervalued talent making this possible if owner Stu Sternberg keeps crying poor and looking for international handouts in the form of a fancy new stadium. The Rays don’t actually need magic Would You Rather bucks to be able to retain some of their players past team control and even swing for top-tier free agents, but as a fan you should want whatever it takes to get them to start spending competitively.

You can be proud of the largely anonymous roster that eliminated a team that spent more on Gerrit Cole than your entire roster combined. But having Gerrit Cole on your team seems pretty cool if you’re into baseball. And also maybe those other guys should be paid more.

Ultimately this comes down to whether you want the team to prove it can do without, or to lose that identity entirely in favor of deeper pockets.

My pick: I probably tipped my hand a little heavily on this one, but I think you gotta go for Yankees-level payroll. Of course, that’s because I’m less a fan of the Rays and more a fan of growing the game and rewarding the labor. And in fact, the former option of winning the World Series now, while seemingly unrelated to economics, could create a blueprint for cheap success that would take an even firmer hold throughout the game as successful front office tactics tend to do and suppress payrolls around the league.

The players themselves shouldn’t be penalized for cheap management that’s already costing them (literally). I just want these guys to get paid, and then get back to October.

Atlanta Braves' Max Fried pitches against the Washington Nationals during the first inning of a baseball game Saturday, Sept. 5, 2020, in Atlanta. (AP Photo/John Amis)
Could Max Fried form a new triumvirate of aces in Atlanta with Mike Soroka and Ian Anderson? (AP Photo/John Amis)

Atlanta Braves

The Choice: If you are a Braves fan, would you rather guarantee that your team wins the World Series this year, OR that Mike Soroka, Max Fried, and Ian Anderson pitch together for 10 years as perennial Cy Young contenders?

The tension here comes from the historical parallels. The Braves enjoyed a rotation of three Hall of Famers who pitched together for a full decade and sent the team to the postseason basically every year during that stretch. And in that time, they only won one World Series — in what was also a shortened season with a newly expanded postseason.

So Braves fans who remember the entirety of the ‘90s are working with some lived experience to draw on. Is an abnormal championship satisfying or will it leave you slightly disappointed? How much did you enjoy the years of historic shutdown pitching that didn’t end in a ring?

This is similar to the Dodgers’ deal in that both ask fans how much they value the immediate triumph of a team that seems well-situated to aspire for more, after learning intimately how even the best can’t bank on being back next year.

This time, there’s no guaranteed failure. Maybe you choose the World Series win in 2020 and the trio of young pitchers still grow into worthy successors to Greg Maddux, Tom Glavine, and John Smoltz. Maybe you opt for the sustained pitching success and that leads to multiple championships starting this year.

The choice this time is between which unsaid occurrence you feel more confident could happen without your magical guarantee. And, in both opposition and conjunction, which guarantee would be sufficiently satisfying if the other options falls apart. Would the memory of a 2020 World Series championship be enough if the pitching potential is never fully realized? Would you curse the year they came so close if the dominant rotation is wasted over the next decade?

My pick: Give me the incredible narrative gift of a Braves team boasting another Big Three.

I’m starting to realize that not being a lifelong, diehard fan of any of these teams makes the decision to punt on a championship all too easy for me. Someone will win this year and that will be fine but I want to know what else can happen.

I’m extrapolating a whole lot about a trio of very promising but very inexperienced arms by projecting them as potential Hall of Famers. But that’s sort of the point. So far this October, the Braves have demonstrated — even without Soroka available to contribute — the incredible watchability of a reliable top of the rotation. Pitchers fall short of their ceilings — either because they just never seem to put it together or because they’re plagued by injury — all the time and the story becomes one of dehumanizing declining value. Even if they never win a World Series, I want to see the young talent grow into superstars.

Houston Astros Carlos Correa rounds the bases after hitting a solo home run Tampa Bay Rays relief pitcher Peter Fairbanks during the sixth inning in Game 2 of a baseball American League Championship Series, Monday, Oct. 12, 2020, in San Diego. (AP Photo/Gregory Bull)
Astros shortstop Carlos Correa has asked what fans would say if the scandal-plagued team keeps winning in 2020. (AP Photo/Gregory Bull)

Houston Astros

The Choice: In this scenario, you are not an Astros fan and the team does win the World Series this year. Would you rather find out later that they were still cheating in some way OR know beyond a shadow of a doubt that they were not?

Now is a good time to remember that this is a fun and silly story rife with hypotheticals. As far as I know and as far as you know, the Astros are not cheating. I don’t think they’re cheating! This is not about that.

Rather, I’m curious if the other 29 fanbases could handle having to hand it to Astros.

We’ll never know if the 2017 team could have won a championship without stealing signs. The truth is they were not all evil and no talent, and making it back to the postseason in the years since proves that. But for fans who haven’t yet had the chance to boo and bang trash cans when baseball’s unambiguous villains come through town, that’s unsatisfyingly nuanced.

Now imagine if they spent all next season as the reigning champions. After they didn’t seem all that sorry! The players would be rightfully smug. And you, fan of any other team, would seem stuck in the past, a sore loser even, if you kept harping on the time they were outed as cheaters.

Under those circumstances, would you sacrifice some of the sanctity of the game, undoubtedly undermining some of its future vitality, for the sake of retaining the moral high ground? You never trusted that Manfred guy anyway. And you knew there was something up about the buzzers. Wouldn’t it be just a little fun to do it all again after everyone turned on the team anyway? Without a pandemic to put it all in perspective and keep you from tormenting them in real time.

Of course how could you call yourself a fan after wishing for the degradation of the game? These are real people’s lives — both the winners and the losers deserve satisfying closure. The sign-stealing scheme was wrong, but the reaction that followed bordered on dangerous.

So, do you want believably fair baseball, or do you want a Marvel universe with clear-cut bad guys?

My pick: I’m not sure baseball can survive if those publicly outed as cheaters prove to be both unrepentant and impossible to police. The Astros winning fair and square is enough of a storyline even if it muddies the narrative. Honestly, they’re probably not cheating. They’re competitive, motivated, and talented. They might win and then we all will, in fact, have to hand it to them.

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