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The Cubs currently have a 12.3 percent chance to win the World Series in 2016. That’s according to BP’s own playoff odds report (POR), which runs one million simulations of the season-to-come, and reports the percentage of those simulations in which a certain outcome (in this case, the Cubs winning the World Series) occurs.

As it turns out, a 12.3 percent chance of winning the World Series is really good. Just two teams—the Indians and Dodgers—have better chances in 2016, according to the model, and there’s a three-point drop from the Cubs to the next-best team on the rankings (the Mets, at 9.4 percent). The POR thinks that the Cubs are about 3.7 times more likely to win a championship than you would expect them to be if such things were left entirely up to chance.

But is this the best shot the Cubs have ever had at winning the World Series? Of course not. Seven times since 1945, the Cubs have made the playoffs but not advanced to the World Series. Surely, on at least some of those seven occasions, there came days when the North Siders’ chances of finally quenching a decades-long thirst were higher—in some cases, quite a bit higher—than they are right now.

How much higher? When were those moments? Let’s find out, with as much precision as we can. Let’s find seven moments where the post-War Cubs were as close as they’ve ever been to winning the World Series. The were probably other moments worth discussing in non-playoff years, of course, but limiting ourselves to seasons in which the team actually made the playoff significantly limits the number of assumptions we have to make. And, as you’ll see shortly, there’s more than enough here to talk about.

We’ll proceed in order, starting in 1984.

***

35.5 percent — October 4, 1984. Cubs up 2-0 in the NLCS.
Here’s what actually happened in 1984: The Ryne Sandberg-led Cubs won 96 games under first-year Chicago manager Jim Frey (he’d managed parts of two seasons in Kansas City earlier in the decade), and advanced to the National League Championship Series—then, best of five—to face the 92-win San Diego Padres, led by Tony Gwynn and Kevin McReynolds. The Cubs went up 2-0 in the NLCS on the back of strong pitching by Rick Sutcliffe and Steve Trout, but then lost the last three games (all in San Diego) to drop the NLCS.

So where did their chances stand on the morning of Thursday, October 4th, when they had yet to lose Game Three (or Four or Five)? To work that out, we have to work out (a) the Cubs’ chances of winning any individual game in the series, and then (b) the Cubs’ chances of winning the series, given those game chances. If you don’t like #GoryMath, please feel free to skip ahead to the end of this section—but be warned, the techniques we use here are the ones we’ll use throughout.

We can find part (a) by using a tool developed by (who else?) Bill James, known as log5. Log5, in a nutshell, calculates the probability of any given team winning a game, given only its winning percentage and that of its opponent. Of course, in a real game situation, a lot is dependent on that night’s starting pitcher and a million other factors, but this is a reasonably good estimator for our purposes.

One twist: Instead of plugging the actual winning percentage into log5, let’s use the pythagorean win percentage reported by Baseball-Reference (here, for example, for the 1984 Cubs). It’s a blunt tool, and there are better ones—including here, on our site’s Adjusted Standings page—but it does go back to 1984, and allows us to use a better estimator of a team’s true talent level than winning percentage.

Plugging the Cubs’ (.565) and Padres’ 1984 (.537) pythagorean win percentages into my log5 calculator, we can estimate the Cubs’ chances of winning any individual game in the series at approximately 52.85 percent. What did that mean for their chances of winning the NLCS, after they’d won the first two games? Here we turn to a wonderful tool built by Steve Saude over at The Hardball Times, which estimates a team’s chances of winning a series of any length based on their chances of winning any individual game—which are exactly the chances we now have.

Plugging the Cubs’ 52.85 percent chances of winning any individual game into a five-game series, with games one and two set at 100 percent (remember, the Cubs won them!) gives the Cubs an 89.5 percent chance to win the NLCS in San Diego, and therefore advance to the World Series. And what were their chances there? Repeating the log5 process for the Cubs and the 102-win Tigers (the eventual AL champions), we get Cubs' chances of 45.27 percent for winning any individual game in the World Series that year. Plugging that into Saude’s tool gives the Cubs a 39.7 percent chance of winning the World Series, had they got there.

Multiply 39.7 percent by 89.5 percent, and you get overall chances of 35.5 percent, on the morning of October 4th, 1984, that the Cubs would win the World Series in 1984. Which is a lot higher than zero, which is how many games they won that year from that point forward. Bummer.

Game Chances vs. SDP

Series Chances vs. SDP

Game Chances vs. DET

Series Chances vs. DET

0.5285

(G1: 1.000)

(G2: 1.000)

0.895

0.4527

0.397

19.3 percent — October 7, 1989. Cubs tied 1-1 in the NLCS.
In 1989, the Cubs returned to the NLCS (which by this time had been extended to a best-of-four series), this time to face the 92-win Giants, led by Will Clark and Kevin Mitchell, and managed by Roger Craig. They split the first two games at Wrigley, then proceeded to drop all three at Candlestick Park and head home disappointed yet again. When were their chances best that year, and how high were they?

As it turns out, the Cubs’ odds were best at some point during Game Three. The Cubs’ true talent that year was .556, and the Giants’ .568, which gave the Cubs just a 48.75 percent chance of winning any individual game. Over the series, that translated into a 47.3 percent chance of advancing to the next round, and after splitting the first two games the Cubs' chances of advancing had improved slightly to 47.7 percent. So the Cubs’ best chance that year must have come during Game Three sometime.

Unfortunately, Fangraphs’ game charts don’t run back to the 1989 postseason, so we can’t pinpoint the exact moment the Cubs’ chances were highest during Game Three, and will have to settle for “the morning of October 7th” as our best answer. But we can add in their chances against the AL-champion A’s (45.58 in any individual game) to get a probability of winning the World Series (had they made it) of 40.4 percent. Combine that with the 47.7 percent chance of advancement we just found above, and you get a 19.3 percent overall shot to win the Series in 1989. Which is not damn bad, when you think about it, and still better than the 12.3 percent we have right now.

Game Chances vs. SFG

Series Chances vs. SFG

Game Chances vs. OAK

Series Chances vs. OAK

0.4875

(G1: 0.000)

(G2: 1.000)

0.477

0.4556

0.404

2.2 percent — September 30, 1998. Cubs about to play the NLDS.
In 1998, after a summer for the ages (remember how much you liked Mark McGwire and Sammy Sosa back then?) the Cubs beat the Giants in a one-game playoff to advance to the NLDS against the 106-win Braves. They were, predictably, swept, and the best Yankees team of any of our lifetimes won the World Series.

This makes sense. Given the Cubs’ Pythagorean W/L, their chances of winning any given game in the series against the Braves were just 36.84 percent, and their chances of advancing any further just 26.4 percent. Had they advanced, they’d have faced the 98-win Padres, where their NLCS chances were 39.2 percent, and if they’d won that, their World Series chances against those 114-win Yankees were just 20.9 percent. Multiply them all together, and you get just 2.2 percent chances of winning the World Series, on September 30th, when they had yet to play a game.

All of which is to say, when you’re going up against two 100-win teams in a given postseason—including maybe the best team of our lifetimes—you have very little chance of success. The Cubs have better odds now, which is sort of counterintuitive, but also makes sense: it’s probable they’ll make the playoffs, and face much poorer opposition when they do.

Game Chances vs. ATL

Series Chances vs. ATL

Game Chances vs. SDP

Series Chances vs. SDP

Game Chances vs. NYY

Series Chances vs. NYY

0.3684

0.264

0.4503

0.392

0.3556

0.209

34.5 percent — October 14, 2003. One out in the top of the eighth, NLCS Game 6.
Ah, 2003. I’m guessing you don’t need me to tell you what happened here, but I will anyway, because I guess I’m just kind of mean. On October 14th of that year, the Cubs were playing Game 6 of the NLCS. They’d won three of the first five games of the series, and were thus a win away from advancing to the championship round for the first time in nearly 60 years. With one out in the eighth inning, they were up 3-0 and, as I’m sure you’ve heard before, “five outs away.”

Then, disaster. An eight-run inning—highlighted by an Alex Gonzalez error—put the Marlins ahead for good in Game Six, and the Fish would go on to win Game Seven 9-6, and the World Series against the Yankees’ later on. But how good were the Cubs’ chances of winning it all after Mike Mordecai flew out to start the Marlins’ half of the eighth?

Pretty darn good, I’m sad to say. Fangraphs estimates the Cubs’ chances of winning the game, at that point, at 95.6 percent, which was the highest mark of the contest. Combine that with a 48.76 percent Chicago chance of winning Game Seven (derived using the usual log5 method), and the Cubs, at the time Mordecai flew out, had a 97.7 (!) percent chance of advancing to the World Series. Once there, they’d have had a 35.3 percent chance of defeating the 101-win Yankees, thus giving them, at that very moment, a 34.5 percent chance of reaching the promised land in 2003. Which is quite good. Not as good as 1984, but more devastating, given the circumstances.

Game Chances vs. FLA

Series Chances vs. FLA

Game Chances vs. NYY

Series Chances vs. NYY

G6: 0.956

G7: 0.4876

0.977

0.4315

0.353

8.5 percent — October 3, 2007. None out in the top of the third, NLDS Game 1.
In the first year of Lou Piniella’s turbulent reign in Chicago, the Cubs surprised just about everybody—including, probably, themselves—when they secured a National League Central division title on the backs of a relatively middling 85-win campaign. As it turned out, their troubles were for naught. The Soriano/Ramirez/Lee-led Cubs were swept 3-0 in the NLDS by the Diamondbacks, and retreated to Wrigley to lick their wounds for the winter (we’ll get to 2008 shortly).

As it turns out, despite the Diamondbacks being pretty bad themselves (a .488 Pythagorean W/L), the Cubs never had much of a shot in 2007. Their chances against the Diamondbacks were pretty good—59.2 percent to win the series, coming into it—but against the Rockies (45.3) and Red Sox (31.3) they were in a much worse position, leading to an overall chance to win the World Series of 8.4 percent.

But we can be kinder to the Cubs. Their chances in each individual game against the Diamondbacks were pretty good, as we said—54.93 percent, by log5—but at one point in Game One (which they ended up losing) their chances were even better than that. Once Carlos Zambrano had doubled to lead off the third (remember how he could hit?), FanGraphs put the Cubs’ chances of winning the game at 56.6 percent. Plug that into Saude’s model, and you get a slightly better NLDS chances of 59.8. Multiply that with the chances of the Cubs winning the NLCS and the World Series, and you have overall chances of a title—as Zambrano stood on second, that October night—of 8.5 percent. Small, but it counts.

Game Chances vs. ARI

Series Chances vs. ARI

Game Chances vs. COL

Series Chances vs. COL

Game Chances vs. BOS

Series Chances vs. BOS

0.5493

(G1: 0.566)

0.598

0.4786

0.453

0.4120

0.313

24.2 percent — October 1, 2008. None out in the bottom of the fourth, NLDS Game 1.
The Cubs returned to the NLDS in 2008 a much better team than they had been the year before, winning 97 games and pacing the National League in most offensive categories. It didn’t make much difference in the end, though, as they went three and out against the Dodgers in the NLDS, and returned home early for a second straight series. This was somewhat surprising, as they were favored in every series they might have played that year: 63.5 percent against the Dodgers, 57.8 against the Phillies, and 59.1 against the AL-champion Rays.

But, again, we can be kinder to the Cubs here than just looking at the pre-Game One odds. In that game, the Cubs were briefly up 2-0 on the back of a Mark DeRosa homer, and their odds of winning shot as high as 77.9 percent after Casey Blake lined out to end the Dodgers’ fourth. Plug that value in for Game One, instead of the normal 57.28 chances for the other games, and you get a 70.9 percent chance of the Cubs winning the NLDS against the Dodgers. Run together with the numbers we already have for the Phillies and the Rays, and you get an overall shot at winning it all, on that Chicago night, of 24.2 percent. This one is much higher than you might expect, given the Cubs didn’t advance, but it speaks to the strength of that Cubs team.

Game Chances vs. LAD

Series Chances vs. LAD

Game Chances vs. PHI

Series Chances vs. PHI

Game Chances vs. TBR

Series Chances vs. TBR

0.5728

(G1: 0.779)

0.709

0.5358

0.578

0.5420

0.591

27.0 percent — October 17, 2015. None out in the top of the fifth, NLCS Game 1.
I’m not even going to break it down in detail, because the memories are too raw. Here are the facts: the Cubs beat the Pirates in the Wild Card Game, beat the Cardinals in the NLDS, and then fell 4-0 in the NLCS to watch the Mets advance. In Game One, though, the Cubs had as much as a 59.1 percent chance to win the game, after a fifth-inning Starlin Castro double that tied the game at one. Combine that with the Cubs’ 50.62 percent chances to win the other games, coming into the series, and you get a 54.0 percent chance to advance to the World Series.

Once there, the Cubs would have faced the Royals, against whom they’d have been projected dead even—50 percent—chances to take home the title (both teams had pythagorean W/L’s of 90-72—though, in fairness, the Royals would have had home field, a factor we opted not to consider in these maths). Multiply the two together, and you get last year’s chances: 27.0 percent to win the World Series, at exactly the moment in time that the Cubs’ soon-to-be-departed hero stood on second, and the game stood tied at one. How depressing.

Game Chances vs. NYM

Series Chances vs. NYM

Game Chances vs. KCR

Series Chances vs. KCR

0.5062

(G1: 0.591)

0.540

0.5000

0.500

***

Phew. We finished. I encourage you, again, to check out my log5 calculations here, though please remember that I used the pythagorean, not actual, win percentages to run the numbers. Once you have those, you can easily check my math on the series projections using the second calculator Saude developed, here. But enough of that. Let’s get to a summary:

Year

Furthest Round

WS Chances

1984

NLCS

35.5 %

2003

NLCS

34.5 %

2015

NLCS

27.0 %

2008

NLDS

24.2 %

1989

NLCS

19.3 %

2007

NLDS

8.5 %

1998

NLDS

2.2 %

I suppose there are two surprises here. The first is that 2008—when the Cubs never made it past the NLDS—rates above 1989, when they did, but the difference here is that the 1989 Cubs would have had to face a very good A’s club in the World Series, whereas the 2008 version had a somewhat easier time of it with the Dodgers, Phillies, and Rays. More the point, the 2008 team was much better than the 1989 club, and that plays into things quite a bit.

The other surprise is that the Cubs’ chances in 1984 and 2003—seasons which have been remembered very differently by the fanbase—rate as essentially identical in this analysis. Part of the discrepancy between the numbers and the perception is the dulling effect of time on memory, but part of it is that the two clubs reached their chances in very different ways.

The 2003 Cubs had a very good chance of winning one game, and then a poor chance of winning the next series. The 1984 version, meanwhile, had a very good chance of winning one game out of three, and then a poor (but somewhat better than ‘03) chance of winning the next series. I suspect that, because the 1984 chance was distributed over three games rather than one, it feels less bad, even though the Cubs should equally have closed things out then (and didn’t). There’s also that a fair number of Cubs fans today weren’t born in 1984, and so don’t remember that one as painfully. An 8-year-old in 1984 is 40 today.

The last thing worth talking about is this: the Cubs’ chances of winning the Series, on at least five different occasions, were better than the 12.3 percent chances we give them right now. It's hard to feel more optimistic about a Cubs roster than many do about this one, and yet: As Sam Miller pointed out in his piece on this site last week, there's a scenario in those POR simulations in which the Cubs lose a lot of baseball games next year. There's another where they lose somewhat less than that, but still a lot more than they’d like to. And all of those bad simulations combine with the good ones to come to a World Series win percentage that's right around 12.3 percent. There's fewer bad projections for the Cubs than there are for most other teams, but there are still a lot, because we don't know what's going to happen yet.

In each of the years the Cubs made the playoffs we considered, we knew what had happened for the vast majority of the season. In 2003, for example, Cubs had won enough games in the regular season to get themselves to a point where they stood five wins away from a title. We didn't have to project out the probability that they'd lose those regular season games (a probability which was not insignificant, before they’d played them). They'd already won them. And being able to build that certainty into the model made all the difference.

The point? 12.3 percent World Series odds are very good, at this point in the season. But nothing beats actually having won the games to get there. And that’s why they play them, year in and year out. This year, the Cubs will try again.

Thanks to Harry Pavlidis and Rob McQuown for assistance.

Thank you for reading

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tomshipley75
3/28
Alternate title: Break Another Little Piece of My Heart. This is a Cliff's Notes for what's like to have been a Cubs fan for that past 30+ years. Can't wait for the installment on the Cleveland Browns.
rianwatt
3/29
Coming soon!
cubsker
3/28
goddamnit
rianwatt
3/29
Sorry :/
quackman
3/28
I was an 8 year old in 1984, and it is a far more painful memory than 2003. Maybe my emotion has to do with having been at game 4 when bleeping Garvey homered, but I think the bigger factor was that the Cubs hadn't been close in so long. By 2003 there was practice at disappointment, but in 1984 it was new.
shorvat
3/29
So, putting it all together, the Cubs had only a 17% chance of *not* winning the Series in any of those years. Impressive.
rianwatt
3/29
Man. This is a disappointing (and correct) way of putting it.