Division play started in 1969, introducing a series to qualify for the World Series. So by 1998, when the Yankees started their run of winning consecutive Pennants, they were actually playing in a tournament and the old World Series (WS) had become the MLB finals. The 1998-2001 Yankees are the only team in the division era to win four consecutive Pennants. The first three also won the WS. Oakland is the only other division era team to win three consecutive WS: 1972, 1973, 1974. These three-peat teams will be compared.
Before divisions were created in 1969 the chances of a team winning the pennant as league champion were 1 in 8 before modern expansion, then:
1961-1968 AL: 1 in 10
1962-1968 NL: 1 in 10
So the chances of winning the WS:
(1/8)/2 = 1 in 16 or 6.25%
(1/10)/2 = 1 in 20 or 5%
Numbers for each year are multiplied to get a total in BOLD. For readability that number is multiplied by 100,000 in the simple column to the right.
In the same 8 team league, obviously winning 5 consecutive World Series is more difficult than winning 4. The lower final number means it's more difficult.
1998 through 2001 a team had a better chance of reaching the tournament but then had to win THREE series. AL divisions 1998-2001:
East: 5
Central: 5
West: 4
The three division winners and the best second place team qualified for the tournament. That's 4 of 14 or 28.6% of teams qualified. But then three 1 of 2 chances to advance:
1903-1960 a team's chances of winning the WS: 6.25%
1998-2001: 3.57%
When Oakland won the WS 1972, 1973, 1974 there were only two AL divisions of six teams each and no wild card. So the chances of reaching the playoff: 1 of 6 or 16.6% compared to the 1998-2000 Yankees 28.6%. But the Yanks had to win three series to be champs and Oakland only two series. The lower final number means it was more difficult:
The 1998-2000 Yankees had a more difficult task winning three consecutive World Series than the 1972-1974 Oakland As.
But if here we're looking at only winning the pennant, i.e., reaching the WS:
1903-1960: 12.5%
1961-1968: 10% in AL
1998-2001: 7.14%
The 1960-1964 Yankees had more than twice the difficulty winning their five consecutive pennants than the 1998-2001 Yankees winning their four. This was a difficult call. If the Yankee odds 1961-1964 had remained 1/8, that team would have had a simple number of 3.05 compared to the 1998-2001 Yankees 2.60, which would have had a more difficult task. It's worth noting that the expansion Angels in year two, 1962, finished third in the AL, so they weren't pushovers at 86-76; and 82-80 in 1964.
Here are all six teams with their rank of difficulty, one being the most difficult.
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