As many (including myself) have noted, this year marks the 100th anniversary of the last Cubs team to win it all. A century of futility—that’s about as pathetic an “accomplishment” as you will ever see in the sporting world.

When looking at that dismal record, it’s natural to wonder what were the biggest botched moments in that period. One way to do it would be endless personal pontificating. I’m pretty good at that, but today I want to try a different approach. Let’s do things more a classically sabermetric way and run a study.

Better yet, how about someone else run a study for me? Elsewhere on this crazy little thing called the internet is a website called the Replacement Level Yankees Weblog currently run by SG. Among his other talents, SG has constructed one of the most fun databases on the planet. He can plug in 28 teams from any year in baseball history and run 1,000 season simulations for them. It just takes him a few days.

Fortunately for me, he thought the idea of doing 1,000 sims of the best Cubs teams since 1908 sounded interesting, and he agreed to do it. He just needed me to pick the 28 teams. It turns out, much to the surprise of some of you I’m sure, that yes, there really have been more than 28 good Cubs teams in that time. They were actually a very good franchise until WWII, and have had some occasional moments since then.

The obvious approach would be to go with the best winning percentages. Clearly, won-loss record is by far the No. 1 factor coming into play here, but it’s not the only one.

While it’s impossible to avoid some redundancy when tabbing 28 seasons out of 100, I want to represent the different eras as best I can. I’d rather have their best season from 1947-66 rather than their worst of the 1930s, even if the latter is a bit better. The last batch of seasons is just to fill out the bracket of 28, so let’s spice up the selection.

###### The teams

With that in mind, here are the teams I submitted:

The 1909, 1910, 1911, 1912 and 1913 Cubs: As noted, it’s impossible to avoid redundancy here. These are the Tinker-Evers-Chance Cubs. They won the pennant in 1910, but got trounced in the Series. The won 104 games in 1909, but the Pirates won 110. They remained good, but in decline, afterwards.

The 1918 Cubs: Won the pennant in a war-shortened season but got run over by a Boston Red Sox rotation led by Babe Ruth.

The 1923 Cubs: This was their best team with Pete Alexander pitching full-time. Better seasons are left out, but this one is bit more distinctive.

The 1928, 1929, and 1930 Cubs: The McCarthy Era in Chicago. They had probably the best outfield in team history with Riggs Stephenson, Kiki Cuyler and Hack Wilson, who had 191 RBIs in 1930. The won the pennant in 1929 and lost two games in the World Series in heartbreaking fashion.

The 1932, 1935, 1937, and 1938 Cubs: There isn’t a really significant break between any Cubs team from 1928-38. Then again, only Gabby Hartnett and Charlie Root survived the entire period. Bill Lee and Lon Warneke were the main pitchers in the 1930s. The outfield gradually broke up, with new bats like Billy Herman aiding the team.

They won the pennants in 1932, 1935, and 1938. They faced historic dynamos in the ’32 and ’38 Fall Classics, but the 1935 team frankly should have beaten the Tigers. The 1937 squad actually had a better winning record than the 1932 or 1938 editions.

The 1945 and 1946 Cubs: They won their last pennant in 1945, and stretched the World Series to seven games. The 1946 Cubs had the franchise’s last winning season for a very long time.

The 1952, 1959, and 1963 Cubs: By winning percentage, none of these teams belongs, especially the 1959 Cubs, which actually had a losing record. These were the most interesting squads in their two decades of torpor between WWII and the Vietnam war.

Rather sadly, the 82-80 1963 Cubs were the best team in that stretch. The 1952 Cubs went .500 led by Hank Sauer‘s big 37-homer season. (Once upon a time, kids, that was an impressive achievement). The ’59 Cubs are the 28th team in this bunch. They’re here to get a season from Ernie Banks‘ prime in.

The 1969 and 1971 Cubs: The ’69 squad led almost all year before the Mets blew them away down the stretch. According to Win Shares, the 1970 team. .. well, apparently I confused them with the 1970 squad, which had a fantastic starting rotation. That’s a mortifying error, but either way, it’s just a team filling out the bracket.

The 1977 Cubs: Going purely by winning percentage, they don’t deserve to be here as they went 81-81. However, the Little Blue Machine actually played at a frantic 61-41 pace into late summer. Then Bruce Sutter‘s arm gave out. And that, ladies and gents, is how the 1970s fireman started becoming the modern closer.

The 1984, 1989, and 1998 Cubs: They all went to the postseason. They are also three of the only five squads with winning records the franchise put together from 1973-2000. It’s been a long century. Here are the clubs I remember. Purely based on my own personal beliefs, I’d say the 1984 squad was the best, and 1998 the least talented.

The 2003 and 2004 Cubs: Well, after 30-plus years, 1969 is no longer the great “What if?” moment in Cubs history. The 2003 team came achingly close to the pennant, and the 2004 squad was probably even more talented.

The 2007 Cubs: Despite starting the year 22-31, they rallied and won a postseason berth. Incredibly, five of the last nine Cubs teams with winning records have made the postseason. Not-so-incredibly, those nine good seasons have come over 35 years.

###### The results

That’s the teams. How about the results? To make it easier to read, I’ll break it into two divisions: up to 1938 and since then. This gives their record, average runs scored and allowed, and also how many times each squad had the best record in the simulations. Due to ties, that number isn’t always an integer. Finally, you’ll have their highest win total in a simulation.

So … what was the best team of the last 100 years? Here are the older teams:

```Team          W        L      RF      RA       #1     High
1910          93      69     712     589     348.5     116
1909          89      73     624     553     116.3     108
1912          87      75     671     617      65.5     107
1935          86      76     682     621      55.5     105
1929          85      77     674     633      46.3     102
1911          83      79     634     603        33     104
1930          83      79     636     612        27     105
1937          82      80     676     662        11     103
1918          81      81     584     566        14     102
1913          81      81     700     691      10.3     100
1928          80      82     594     593       6.8      98
1923          78      84     657     680       3.3      99
1938          77      85     601     629       0.7      95
1932          76      86     562     601         2      95```

```Team           W       L      RS      RA       #1     High
2004          88      74     636     586     114.2     110
1945          86      76     639     585      66.2     106
2003          84      78     599     590      34.3     106
1998          82      80     670     686      16.3     106
1989          81      81     679     671        15      99
1984          79      83     658     681         4      96
2007          79      83     596     611       4.8      99
1952          77      85     588     625         1      95
1969          77      85     616     656         1     103
1977          76      86     583     664       1.3      95
1946          75      87     630     686         1      92
1971          75      87     621     685         0      94
1959          74      88     581     652         0      95
1963          74      88     593     663       0.5      97```

So the 1910 Cubs came in first. Well, like all Cubs teams from that era, they did a fantastic job preventing the other team from scoring. Three Finger Brown had one of his best seasons, going 25-13 with a 1.86 ERA while leading the league in saves.

While the staff allowed the fewest runs in the league, the offense scored more runs per game than any other team in baseball. Not bad considering they played in a pitcher’s park. None of the hitters had a great season, but pretty much everyone had a good season. That’s classic Cubs ball from back then. Of the 11 with at least 100 plate appearances, nine had an OPS+ of 100 or better. The low was 88.

In the World Series, the A’s battered them. The Cubs led for about five innings while getting outscored 35-15. It wasn’t so much the Cubs underachieving as it was that good an A’s squad. They won three titles and four pennants in five years. That’s the best stretch Connie Mack ever had.

The 2004 Cubs are the best squad the team has put together since the days of Johnny Evers. That’s not terribly surprising. Sure, Kerry Wood and Mark Prior combined for only 43 starts, but Carlos Zambrano had what’s still the best season of his career, as did Matt Clement. Their other starter was some guy named Maddux. Meanwhile, almost every regular position player gave them a good season.

There are many reasons to be mournful for that team’s failure down the stretch. I’ll just point to one. Late in the year, Prior came off the DL and pitched up to his lofty potential. In his final three starts, he allowed two runs in 24.2 innings. In his last game, he struck out 16 in nine innings while allowing only four base runners.

Had they made the postseason, they would’ve had a dangerously effective Mark Prior on their side. They didn’t and he has never been as good since then.

What’s also surprising at these results is how poorly the 1932 and 1938 pennant winners did. Well, the 1938 team isn’t so surprising. They were a team that took it when no one was that good in the NL. I have no perfect explanation for 1932, accept to note that they did exceed their Pythagorean record by four games.

###### The other half: the worst teams

Maybe it’s the masochist in men, but I’m also curious to see what the worst Cubs team over the last 100 years was. Fortunately, SG wasn’t doing anything else with his super simulation machine so…

I used the same basic guidelines to choosing teams. There is increased redundancy because the 1947-66 era dominates the terrible years like no other stretch in the previous simulation. Plus they’ve had sustained periods (long, long ago) of very good teams. Here are the squads:

The 1916, 1921, and 1925 Cubs: These are the only really bad teams prior to the Homer in the Gloamin’. The 1925 season was their only last-place finish from 1876-1947.

The 1940 and 1942 Cubs: The former was their first losing season in almost 20 years. The latter was their worst year of the WWII era.

The 1948, 1949, 1950, 1951, 1953, 1954, 1956, 1957, 1960, 1961, 1962, and 1966 Cubs: Describing each one of these teams would be as boring as they were bad. Let’s put it this way, in 130-plus years of frequently forgettable baseball, the Cubs have only had 16 seasons where its winning percentage was worse than .418. 10 came in this period. Plus they went exactly .418 in 1950, and .422 three years later.

The 1974, 1980, and 1981 Cubs: The worst years in the late Wrigley period. In one 162-games stretch from June 6, 1980 to June 4, 1981, they went 52-110. That’s their worst period ever.

The 1983 and 1985 Cubs: The former actually nearly scored as many runs as they allowed, but still lost over 90 games. The latter was in first place in June, but then their entire starting rotation went down with injury.

The 1994, 1997, 1999, 2000, 2002, and 2006 Cubs: Sure, any team can have a bunch of bad seasons with a low payroll, but the Tribune-era Cubs have actually spent a decent chunk of money turning out terrible teams. That’s a mark of distinction.

Let’s get it over with. Twos wrinkles: the column on the right gives their fewest wins in any sim, and will rank them from worst to best. Here are the biggest blechs of the blighted. Older half:

```Team          W       L      RF      RA       #1  Fewest
CHN21         75      87     610     654       1      54
CHN49         76      86     576     619       3      57
CHN51         76      86     589     626       1      55
CHN25         77      86     638     673       1      57
CHN48         79      84     601     618       4      59
CHN50         79      83     620     635       5      61
CHN56         79      83     586     601       4      59
CHN53         81      82     645     653       9      58
CHN57         82      80     619     620      15      64
CHN42         83      79     695     664      16      66
CHN60         83      79     637     622      31      61
CHN54         85      78     639     606      34      66
CHN16         88      75     738     673      81      69
CHN40         90      72     692     602     183      68```

Not as old:

```Team          W       L      RF      RA       #1  Fewest
CHN66         74      88     645     698       0      57
CHN81         76      86     631     674       2      56
CHN97         76      86     601     650       2      55
CHN62         77      85     610     646       1      57
CHN99         77      85     621     654       2      56
CHN00         80      82     635     645       7      58
CHN80         80      82     635     647       3      62
CHN74         81      81     686     689      10      57
CHN85         83      80     697     699      14      64
CHN06         83      79     631     624      15      65
CHN94         83      79     633     626      19      64
CHN61         85      78     679     647      35      64
CHN83         90      72     748     667     164      71
CHN02         93      69     682     588     339      80```

The 1966 Cubs do the worst. Makes sense, as they lost 103 games in real life. It gives one a whole new depreciation for the 1921 squad as well.

###### Summing up

One interesting thing is that the Cubs never really had a sure-fire squad in all this time. They had plenty of very good teams, but never one real “A-ha!” they that should have done. Their best came along at bad moments. The 1909-10 teams had better Pirates and A’s teams to contend with. Sure, the 2004 squad should have made the playoffs, but the Cards won 105 and the Red Sox were baseball freaking demigods in the World Series.

Alternately, while they’ve had their troubles, they’ve almost never been truly gruesome. The franchise has lost 100 games only twice.

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