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Rays Betting Series: MLB Dream Bracket Pool

An oasis in the desert

Sports Betting In Delaware Photo by Stan Grossfeld/The Boston Globe via Getty Images

In case you missed it, yesterday I posted a massive overarching preview of what I think is one of the coolest things MLB has done in a long time: The MLB Dream Bracket. (Here’s a link to my preview yesterday, and here’s a link to’s introduction to the event, which kicks off tomorrow.)

One of the best parts of this idea: sports betting is back! And not just the random soccer leagues in tiny Eastern European nations that you were relying on for the past month while the world came to a halt. Real, live sports betting!

Well, not totally live. This is a simulation after all. But it’ll have to do for now, and it should be plenty of fun breaking down just exactly what kind of trouble sports bettors can get into with the betting surrounding this bracket.

Where to Bet

DraftKings has partnered with MLB for this undertaking, and they are providing some cool betting options. The premier offering is a Free to Play Pool with 13 questions regarding the bracket. Let’s take a look at them:

1) Who will win the Tournament?

Options: Red Sox, Cubs, Astros, Dodgers, Yankees, Phillies, Nationals, Any Other Team

This one blew my mind. If you checked out my preview yesterday, you know that neither of the top two teams I had in those rankings is listed as a choice here (the Giants and the Negro League All-Stars). Given that fact, along with how crazy simulations get, and the fact that everyone and their uncle is going to be on the Yankees/Red Sox train, I don’t see how the best play is anything other than “Any Other Team.”

(By the way, I find it hilarious that they included the Nationals here as if someone was following baseball for only one year and was like, hey they’ll probably win this thing too!)

2) Which league will the winner be from?

Options: American League, National League

This one is a lot closer, and is one of those classic pool picks that’s basically a coin flip. Going by those power rankings I did yesterday, I can really only see 11 teams winning this, and given that six of those 11 are in the AL — including two of the top three — I’ll lean slightly that way.

3) Which team will advance further?

Options: Yankees, Red Sox, Eliminated Same Round

This is a fun one for haters of both teams, and maybe even closer than you’d think given that the Yankees first two opponents (Mariners and Negro League AS) are superior to the Sox competition (Rangers and the winner of Twins/Blue Jays). In fact, let’s use that to our advantage, along with the fact that a lot of people will go the other way, and it’s always good to zag in these pools when there’s an edge to be had.

4) Which team will advance further?

Options: Cardinals, Cubs, Eliminated Same Round

This is a layup in my mind. Cards, easy.

5) Which team will advance further?

Options: Phillies, Nationals, Eliminated Same Round

Well, one franchise has been around for 137 years, and the other for only 52, that being said, I’m actually going Same Round here, as I like the Nats as a potential upset special in the first round, and it’s not as if the Phillies were stockpiling talent in a lot of those years.

6) Which team will advance further?

Options: Dodgers, Giants, Eliminated Same Round

I’m reallllly hoping this is the NL final — that would be legitimately fun to watch play out on Twitter. I’ve put my eggs in the Giants’ basket. Gotta keep them there now.

7) Who will win the American League?

Options: Red Sox, Astros, Royals, Twins, Yankees, Any Other Team

One thing to keep in mind with these Free to Play pool games is you’re going against about a trillion other people, so you’re going to have to A) take a unique approach, and B) stick to that approach if you want to win anything. (Well, that’s assuming you want to go-big-or-go-home, if you just want to finish in the 52nd percentile, you can go ahead and diversify your answers.) Since I already locked in an “Any Other Team” in the first answer, I’ll stick with it here, with the added bonus of getting the two-seed Oakland A’s, who are shockingly missing from the favorites list.

8) Who will win the National League?

Options: Cubs, Dodgers, Phillies, Cardinals, Nationals, Any Other Team


9) Will any player during the Tournament hit a Grand Slam?

Options: Yes, No

These are 31 best-of-seven series, which means around 175 games, and there were 141 Grand Slams hit over the course of the 2430 or so games in 2018, for a rate of one every 16.5 games. Even if the ball was rather friendly in 2018, it’s hard to imagine the whole tournament going without one.

10) Will any player/team during the Tournament pitch a no-hitter?

Options: Yes, No

The odds on this are obviously far lower than a Grand Slam, but there are going to be 150 or so of the greatest pitchers of all time in this tournament, so it’s really tempting to say Yes. However, I think that temptation is going to draw in more folks than it should, when Occam’s Razor (and I) say no.

11) How many series in Round 1 will go 7 games?

Options: 1-3 Series, 4-6 Series, 7 or more Series

I could see Cleveland vs. Negro League AS; Houston vs. Baltimore; Chicago (NL) vs. New York (NL); and Pittsburgh vs. Arizona going seven, but that’s just about the max. I think it’s far more likely only one or two of those do.

12) How many games will the Finals series be?

Options: 4 games, 5 games, 6 games, 7 games

Check out this Ben Lindbergh piece for this question. I said six. Honestly, this one is the least dissectible.

13) Who will the MVP of the Tournament be?

Options: Retired Player, Current Player

This one is more of a layup than you think: Retired.

Further Betting

Since we’re already 1,000+ words in, let’s keep this brief. There’s another pool on DraftKings, focusing on Day 1 of the simulation, which will be the entire first round on the left side of the bracket (American League + Negro League AS).

Brief picks (submit yours in the comments and we can compare how wrong we all were later!)

  • Minnesota over Toronto: Thanks to their Senators’ history, the Twins roster is sneaky stacked, led by The Big Train, himself.
  • Chicago (AL) over Kansas City: The White Sox roster is pretty bleh, but the Royals lineup lacks the pop to win a round in this thing.
  • Oakland over Tampa Bay: :(
  • Houston over Baltimore: The Killer B’s — along with the far less noted Killer C’s of Correa, Cruz, and Cedeno — have enough to power past the O’s in an alphabet spectacular.
  • Boston over Texas: Varitek and A-Rod re-animate the glove swat.
  • New York (AL) over Seattle: Gahhhhh, I wanted this Seattle team to go on a run, so bad; if I had any stones whatsoever, I’d pick them here.
  • Negro League AS over Cleveland: I’m really hoping the sim does the Negro League AS team justice, because if so, they should win it all.

I’m going to see what the general reaction is to these pieces here on DRB, since they’re not really Rays specific. Please let me know in the comments section whether there is actually interest in sustained coverage of this as the tournament goes along. No worries if not, I’ll slide the coverage over to my Medium page, which can be found here.

In the words of Tobias Funke: Let the great experiment begin!