The Cubs Playoff Problem - The Riddler

J. Westin
October 1, 2016
This is my solution to the Five-Thirty-Eight Riddler Cubs World Series Classic problem. The problem is as
follows: The Cubs and the Red Sox are in a best-of-seven playoff round (i.e. first to four wins is victorious).
You are taking even (double or nothing) bets on each individual match. Construct a betting strategy in
which you will always have a net profit or loss of $100, depending on who wins the entire round.

Answer

Here is the proper strategy you should follow in order to win $100 if the Cubs win, and lose $100 if the Red
Sox win.
If, at any point, a team has three wins, keep betting the difference between your current money and $100.
For example, if the current standing is WWLW for the Cubs and you have $75, bet $25. If you lose youll
have $50, and you should bet $50 on the next match. If you lose again youll have $0 and you should bet
$100 on the last match. If the Red Sox have three wins, bet the difference between your net loss and -$100.
In all other situations:
On the first and second match, bet $31.25 on the Cubs
If one team won both of the first matches, bet $25 on the Cubs in match 3.
If both teams won one of the first two matches (WL or LW), bet $37.50 on the Cubs in match 3.
If neither team has three wins, bet $37.50 on the Cubs in match 4.
Similarly, if no team has three wins, bet $50 on the Cubs in match 5.
After five matches, one team has to have three wins. At this point, simply follow the advice from before.
Also follow this advice and ignore steps 4 and/or 5 if somebody has won three matches at any point.

Working

So where does this strategy come from? There are a few things to notice about the betting process.
First, your betting strategy has to be based on your past wins/losses. The only logical basis for adjusting
your strategy is the win/loss history.
Second, you should treat inverted win/loss sequences the same. If the first three matches have a WWL
result or a LLW result, you should bet the same amount on match 4 in both cases. Strategically, you should
consider WWLWL and LLWLW the same, but WWLL and LWLW different. By treating wins and losses
symmetrically like this, youll end up profiting or losing the same amount of cash depending on who wins.
If you bet and get a WWL, you profit k dollars, and in a LLW situation you lose k dollars.

Third, if at any point a team has won three matches, you have to constantly bet with the expectation to
round off to $100 next match. If you have $40 and the Cubs have won three games, you have to bet $60 in
case they win again. You also have to set this up so that when the score is 3-3 in wins, you have a net profit
of zero dollars. This way you can bet $100 on the last game, and youll end up with $100, depending on
who wins (which is what you want).
Heres an example of how we can use the third fact. Suppose the Cubs win the three first games (i.e.
WWW). You now have $k. You have to bet $100 $k on the fourth match in case they win. If they do,
then cool. Mission accomplished. If not, you now have $2k $100 because you lost. On the next match
youll have to bet $2k $200. If you lose, youll have to bet $4k 400 on match 6. If you lost, you now have
$8k $700. Since the score is WWWLLL, the next game is deciding so youll want to have $0. Therefore,
8k 700 = 0 k = 700/8 = 87.5. k is the amount of cash we had after match 3, so we want that to be 87.5
dollars. So if we bet A, B and C dollars on matches 1, 2 and 3 respectively, we want A + B + C = 87.5
Similarly, if a team wins its third match in match 4, youll need to have $75 at that point. If nobody wins
three matches until match 5, you need to have $50 after match 5. After match 5 its guaranteed that one
team will have won three matches.
There are ten distinct ways in which both teams can win three matches. Here they are, listed assuming the
Cubs win three matches first. There are ten similar situations for the Red Sox. W and L stand for
a Cubs win and a Red Sox win, respectively. The letters A - J stand for different amounts of money you
should bet on the next game, depending on the win/loss history. In game 1, you should always bet A dollars
since there is no history yet. In game 2 you should bet B dollars, since a win and a loss count the same
(see the second point above). If the first two games were won by the same team, bet C dollars on game 3.
Otherwise bet D dollars. The sign indicates whether you won or lost your money.
W
A
W
A
W
A
L
A
W
A
W
A
L
A
W
A
L
A
L
A

W
+B
W
+B
L
B
W
+B
W
+B
L
B
W
+B
L
B
W
+B
L
B

W
+C
L
C
W
+D
W
+D
L
C
W
+D
W
+D
L
D
L
D
W
+C

W
+E
W
+F
W
+G
L
E
L
F
L
G
W
+G
W
+E
W
+F

W
+H
W
+I
W
+J
W
+J
W
+I
W
+H

(1)

As described before, the first equation (A + B + C) should add up to 7/8 of 100 dollars, or 87.5 dollars. The
second, third and fourth equations should add up to 75 dollars. The rest of the equations have a right hand
side of 50 dollars. This leaves us with ten linear equations and ten unknowns, A through J. We can solve
this.
If we solve this system, we get that A and B are 5/16 of 100 dollars, or 31.25 dollars. This means that we
should always bet 31.25 dollars on the first two matches. C and D are 25 dollars and 37.5 dollars, respectively.
2

This means we need to decide between these two amounts on match 3 depending on the win/loss history.
E through G are all 37.5 dollars, meaning we should always bet that much on match 4, assuming nobody
has three wins yet. Similarly, H through J are all 50 dollars, so we should bet 50 dollars on match 5. And
thats all I have to say about that.