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A Cubs fan’s guide to the World Series

Are you cheering for the Rays or the Dodgers?

MLB: NLCS-Atlanta Braves at Los Angeles Dodgers
Mookie Betts stealing home runs
Kevin Jairaj-USA TODAY Sports

Since the Cubs were eliminated from the Postseason my rooting interests for the World Series have generally leaned towards underdogs. I wanted the Rays to beat the Yankees (and they did) I wanted to Padres to beat the Dodgers (they did not).

After two thrilling Championship Series that both went to game seven the stage is set for the Fall Classic and today I’ll cover the three biggest questions I see ahead of tonight’s Game 1.

Can money buy a championship?

You basically cannot field two teams more different in terms of money than the Dodgers and the Rays. The Dodgers have the second-largest payroll in baseball behind only the Yankees. The Rays have the fourth-lowest payroll in baseball, ahead of only the Marlins, Pirates and Orioles. There are good arguments for or against either team here, but the difference is still stark.

The Dodgers side of this equation is basically an argument that top players should be paid. They should get large, long-term contracts and those contracts should be rewarded with wins. The Dodgers paid Clayton Kershaw, Mookie Betts and Kenley Jansen. They should be rewarded for investing in their team with a championship.

The Rays side of this equation is the thesis of Moneyball — for small market teams to win championships they need to identify market inefficiencies and capitalize on those. The Rays have developed talent from within their system and where they have excesses they’ve traded shrewdly to add players like Randy Arozarena who have overperformed their projections.

I’m honestly torn on this point — the pro-player/labor side of me wants the Dodgers to win here and the stats nerd analytics side of me would love to see the Rays triumph.

Starters and bullpens and closers, oh my!

The Dodgers have a traditional rotation built around aces. Kershaw may struggle in the postseason but he’s a first ballot Hall of Famer and an ace. Walker Buehler only threw 36⅔ innings in the regular season, but his career ERA of 3.15 with a K/9 of 10.34 profiles more than favorably as a No. 2 starter. After that Dave Roberts can go with rookie sensation Dustin May or Julio Urías, both of whom profile as more traditional starters, although their innings totals are low.

The Rays do not have a Kershaw, but they do have a Blake Snell, a Tyler Glasnow and a Charlie Morton, all of whom match up favorably with the Dodgers rotation. Plus this is postseason Kershaw, the Rays may actually have a better rotation than the Dodgers.

But honestly, both Dave Roberts and Kevin Cash have quick hooks - sometimes too quick, so maybe what really matters is the bullpen. Here too, it’s a tight race between the two teams. The Dodgers have the third best bullpen in MLB by fWAR with 3.5, the Rays have the best bullpen in MLB by fWAR at 3.6. Both teams closers have struggled at times. The pitching situation in this year’s World Series should be a photo finish.

Whose fans deserve it more?

This is a Cubs blog and this absolutely awful tweet notwithstanding (more on that later today) Cubs fans understand long-suffering. I will never forget heading to Fenway to see the Cubs play in 2011 and having a guy on the green line tell me before I got off at the park “Hey, we hope you’re next.”

There is something that binds together long-suffering fan bases as nothing else can - the question is, which fan base has suffered more?

The Dodgers have not won a World Series since the series where Kirk Gibson hit one of the most ridiculous walkoff home runs in the history of sports. I’m going to put that video here because it’s awesome and you should watch it again:

Yes, it’s more than nine minutes long. Yes, you should watch the whole thing. That’s Vin Scully, after all.

Incidentally, that home run was 32 years ago. It’s a fraction of 108, but it’s still multiple decades. There are still a decent number of Dodgers fans who have never seen their team win a World Series.

And then, we get to the Rays. They are only 23 years old, so while they have never won a World Series, that title drought is still a bit less than the Dodgers. Additionally, outside of sabermetric corners and the baseball obsessed it’s not entirely sure the Rays have fans (I’m sorry, Ashley, I’m sorry). This is the team that MLB proposed spend half their season in Montreal in order to boost attendance.


I think I’m still cheering for the Rays, but I had to think about it for a few minutes before typing that sentence. I almost talked myself into cheering for the Dodgers after watching that Kirk Gibson home run. Then I think of the Rays collection of guys only the biggest baseball fans have ever heard of and I love the idea of seeing them win it all. The best part of this series is with the Cardinals, Astros and Yankees all eliminated there are really no bad answers here.

The pandemic World Series starts tonight at 7:09 p.m. CT on Fox.


Who are you rooting for in the World Series?

This poll is closed

  • 11%
    (20 votes)
  • 77%
    (140 votes)
  • 11%
    (21 votes)
181 votes total Vote Now


The winner of the 2020 World Series will be...

This poll is closed

  • 2%
    Dodgers in four games
    (3 votes)
  • 10%
    Dodgers in five games
    (14 votes)
  • 22%
    Dodgers in six games
    (31 votes)
  • 8%
    Dodgers in seven games
    (12 votes)
  • 0%
    Rays in four games
    (1 vote)
  • 3%
    Rays in five games
    (5 votes)
  • 28%
    Rays in six games
    (38 votes)
  • 22%
    Rays in seven games
    (31 votes)
135 votes total Vote Now