Bryan Knowles did an anti-dynasty list on the old Football Outsiders website, and I decided to make a similar system for MLB.

• The vast majority of the data for this comes from Baseball Reference.

• I didn’t have write-ups for every team that were nearly as long as I envisioned. Partly because it’s hard to think of interesting things to say about terrible teams, and partly because I wanted to get this thing out before Opening Day 2024. But I reserve the right to edit this later and add more tidbits and thoughts about the teams as I develop them.

• I decided to make this list based on the American and National Leagues since 1901. My childhood addiction to Prime 9 brainwashed me into this standard; this standard will envelop the history of present-day AL teams, and most of the history of present-day NL teams; nobody really cares about 19th century baseball, and leagues were less stable back then; Negro Leagues were also often unstable and unbalanced, and it would feel bad to start making fun of NL teams.

• Every season a team finishes under .500 generates points equal to the number of games under .500 they finished. For example, in 2023 the Red Sox (78-84) earned 6 anti-dynasty points, while the Royals (56-106) generated 50.

• If you finish over .500, you earn negative points equal to twice the number of games over .500. For example, in 2023 the Marlins (84-78) earned -12 anti-dynasty points.

• There are four ways that an anti-dynasty can end.

  • If the running count of anti-dynasty points goes to 0 or below, the anti-dynasty ends.

  • If a team’s two-season W-L record equals .500 or better, the anti-dynasty ends.

  • Any LCS or World Series appearance immediately ends an anti-dynasty.

  • An anti-dynasty is determined to end whenever the running count of anti-dynasty points reached its peak. So if a team had accumulated 200 points, but then had an 84-78 season (-12 points), then a 76-86 season (10 points), then started winning, both of those seasons would end up getting cut off from the anti-dynasty, so as to maximize the total number of points that it ends up with.

Snubs

In order to make a top ten of a list like this, you really have to be horrible from just about every possible perspective. A few horrible seasons won’t be enough, and even being under .500 for a very long time might not be enough if you don’t rack up enough points in those years. And slipping up at all can interrupt an otherwise promising anti-dynasty. With that in mind, here are some categories of teams who you might have been looking for, but didn’t make this list.

Impressive Losing, but not sustained for long enough: ‘62-68 Mets (343 points), ‘98-07 Devil Rays (327), ‘09-14 Astros (208), ‘17-21 Orioles (202)

Bad for a long time, but not bad enough: ‘98-11 Orioles (286), ‘10-22 Marlins (252), ‘93-06 Brewers (238)

Interrupted by brief oases: ‘69-93 Indians (collectively 381 below .500 but the highest anti-dynasty is 208), ‘46-61 Senators/Twins (collectively 409 below, highest anti-dynasty is 238)

Just missed the cut: 1917-31 Braves (412), 1902-13 Cardinals (410), ‘30-41 Browns (407), ‘89-05 Tigers (379), ‘77-94 Mariners (374), ‘69-81 Padres (371) [These aren’t all of the teams that barely missed, but the top few and a selection of teams you might have been looking for.]

10. St. Louis Browns/Baltimore Orioles, 1946-1959 (414 points)

Total Record: 869-1,283-12 (.404, 66-win pace over 162 games)

Total Runs:

Five Worst Seasons: 1955 (57-97-2), 1954 (54-100), 1953 (54-100), 1949 (53-101-1), 1951 (52-102)

Five Best Seasons: 1946 (66-88-2), 1956 (69-85), 1959 (74-80-1), 1958 (74-79-1), 1957 (76-76-2)

Median Seasons: 1947 (59-95), 1948 (59-94-2)

Top Five Players in fWAR: Ned Garver (15.8), Bob Nieman (15.2), Gus Triandos (13.7), Connie Johnson (11.1), Billy O’Dell (9.4)

The St. Louis Browns were bad for almost all of their history, but they had just enough bright seasons here and there to avoid making this list multiple times (though they have a 407-point run and another, 320-point run).

9. Pittsburgh Pirates, 1993-2012 (422 points)

Total Record: 1,374-1,796-1 (.433, 70-win pace)

Total Runs: 13,566 scored, 15,552 allowed

Five Worst Seasons: 2008 (67-95), 1995 (58-86), 2009 (62-99), 2001 (62-100), 2010 (57-105)

Five Best Seasons: 2003 (75-87), 1994 (53-61), 1999 (78-83), 1997 (79-83), 2012 (79-83)

Median Seasons: 2000 (69-93), 2011 (72-90)

Top Five Players in fWAR: Jason Kendall (31.5), Brian Giles (28.8), Andrew McCutchen (19.5), Paul Maholm (14.7), Jason Bay (14.4)

When I think about the most painful losses in the history of sports, the 1992 NLCS often comes to mind for me. That’s based on the theory that a loss can be aggravated either in the moment, because it was known that a team’s window was closing, or in retrospect, once we know that a team did not recover from a loss for quite a long time. In this case, both of those factors were present. My understanding, at least, is that everyone knew the Pirates were on their swan song, though of course nobody could have predicted that they would not have a winning season for another two decades.

8. Kansas City Royals, 1995-2012 (430 points)

Total Record: 1,230-1,664 (.425, 69-win pace)

Total Runs: 13,216 scored, 15,228 allowed

Five Worst Seasons: 1999 (64-97), 2006 (62-100), 2002 (62-100), 2004 (58-104), 2005 (56-106)

Five Best Seasons: 2008 (75-87), 1996 (75-86), 2000 (77-85), 1995 (70-74), 2003 (83-79)

Median Seasons: 1997 (67-94), 2007 (69-93)

Top Five Players in fWAR: Carlos Beltran (24.9), Zack Greinke (23.8), Mike Sweeney (20.1), David DeJesus (19.8), Kevin Appier (18.6)

If you’re liking these modern teams, you’d better savor them! The Royals are not only the highest anti-dynasty which includes the 21st century, they’re the highest in the whole divisional era. They just don’t make anti-dynasty like they used to in the good ol’ days.

For some reason, I think these Royals tend to fly under the radar relative to the Pirates and Orioles in the same timeframe. Maybe it’s east-coast bias, or maybe it’s the fact that these Royals didn’t have a clean streak of losing seasons like the other two teams did (because of 2003 being slightly over .500).

7. Philadelphia Athletics, 1915-1924 (435 points)

Total Record: 528-963-12 (.355, 58-win pace)

Total Runs: 5,656 scored, 7,733 allowed

Five Worst Seasons: 1921 (53-100-2), 1920 (48-106-2), 1915 (43-109-2), 1919 (36-104), 1916 (36-117-1)

Five Best Seasons: 1917 (55-98-1), 1918 (52-76-2), 1922 (65-89-1), 1923 (69-83-1), 1924 (71-81)

Median Seasons: 1917 (55-98-1), 1921 (53-100-2)

Top Five Players in fWAR: Eddie Rommel (14.3), Tilly Walker (12.4), Rollie Naylor (11.8), Amos Strunk (10.5), Slim Harriss (10.2)

The A’s had won four of the last five pennants, but after losing the 1914 World Series, Connie Mack decided to burn the roster to the ground, starting a streak of 7(!) straight seasons in last place. That’s something nobody else in this top ten managed, even given that some of them were working with divisions with fewer than 8 teams. If this is a record, I’d have to imagine it’s close to an unbreakable one.

6. Chicago Cubs, 1947-1966 (440 points)

Total Record: 1,338-1,780-19 (.430, 70-win pace)

Total Runs: 12,663 scored, 14,747 allowed

Five Worst Seasons: 1949 (61-93), 1960 (60-94-2), 1956 (60-94-3), 1966 (59-103), 1962 (59-103)

Five Best Seasons: 1964 (76-86), 1955 (72-81-1), 1959 (74-80-1), 1952 (77-77-1), 1963 (82-80)

Median Seasons: 1950 (64-89-1), 1961 (64-90-2)

Top Five Players in fWAR: Ernie Banks (58.6), Bob Rush (39.5), Ron Santo (34.5), Billy Williams (25.7), Dick Ellsworth (21.9)

Much like the Pirates, the Cubs were bad for a very long time, although the quality of badness isn’t quite rich enough for them to crack the top five, compared to teams we’re about to see who would be averaging 100-loss seasons with a 162-game format.

Ernie Banks, Bob Rush, and Ron Santo are three of the top four players on this list as far as accumulated fWAR while playing for an anti-dynasty.

5. Boston Nationals/Doves/Braves, 1903-1913 (465 points)

Total Record: 597-1,062-29 (.362, 59-win pace)

Total Runs: 5,947 scored, 8,070 allowed

Five Worst Seasons: 1912 (52-101-2), 1905 (51-103-2), 1906 (49-102-1), 1911 (44-107-5), 1909 (45-108-2)

Five Best Seasons: 1904 (55-98-2), 1907 (58-90-4), 1908 (63-91-2), 1903 (58-80-2), 1913 (69-82-3)

Median Seasons: 1910 (53-100-4)

Top Five Players in fWAR: Fred Tenney (18.2), Irv Young (14.2), Bill Sweeney (12.6), Vic Willis (10.8), Hub Perdue (8.7)

The 1914 Braves’ turnaround is gobsmacking enough if you just consider the season itself. It would have come as even more of a shock, though, if you considered that these guys had finished double digits under .500 the year before… and that was their best season in over a decade.

In fact, if you paid attention to the snubs list, the Braves quickly got back off the mat and started another anti-dynasty which almost made the list (starting in 1917). So, the second half of 1914, and the two solid seasons which succeeded, was like the oasis in a desert of decades’ full of terrible baseball.

4. Philadelphia Athletics, 1934-1946 (509 points)

Total Record: 736-1,245-16 (.373, 60-win pace)

Total Runs: 8.334 scored, 10,786 allowed

Five Worst Seasons: 1940 (54-100), 1938 (53-99-2), 1936 (53-100-1), 1946 (49-105-1), 1943 (49-105-1)

Five Best Seasons: 1939 (55-97-1), 1935 (58-91), 1941 (64-90), 1934 (68-82-3), 1944 (72-82-1)

Median Season: 1942 (55-99)

Top Five Players in fWAR: Bob Johnson (40.4), Wally Moses (18.6), Jimmie Foxx (17.2), Frankie Hayes (15.0), Sam Chapman (10.5)

Slight spoiler for what’s coming next, but in this era, Philadelphia managed to have two brutally bad teams.

Every single one of their top five fWAR players in this stretch were hitters. The team’s AL ranking in ERA+ in this span, in chronological order: 7th-8th, 7th, 8th, 5th, 7th, 7th-8th, 8th, 8th, 7th, 8th, 3rd(!), 6th, 7th-8th. That’s bottom-two in the league 10 out of 13 times. Ouch.

3. Boston Red Sox, 1919-1933 (517 points)

Total Record: 881-1,398-11 (.387, 63-win pace)

Total Runs: 9,294 scored, 11,803 allowed

Five Worst Seasons: 1930 (52-102), 1927 (51-108), 1925 (47-105), 1926 (46-107-1), 1932 (43-111)

Five Best Seasons: 1933 (63-86), 1924 (67-87-3), 1920 (72-81-1), 1919 (66-71-1), 1921 (75-79)

Median Season: 1922 (61-93)

Top Five Players in fWAR: Howard Ehmke (14.4), Jack Russell (13.5), Jack Quinn (12.6), Ira Flagstead (12.4), Red Ruffing (12.3)

Harry Frazee has just seen his team win its second World Series with him at the helm, and the fourth overall in seven years. He knew he had a dynasty, so he looked 100 years into the future and saw that someone would be making an anti-dynasty list one day. He sold Babe Ruth hoping to kickstart an anti-dynasty, and boy did he ever.

2. Philadelphia/Kansas City Athletics, 1950-1967 (539 points)

Total Record: 1,140-1,683-13 (.404, 65-win pace)

Total Runs: 11,348 scored, 14,039 allowed

Five Worst Seasons: 1965 (59-103), 1964 (57-105-1), 1950 (52-102), 1956 (52-102), 1954 (51-103-2)

Five Best Seasons: 1963 (73-89), 1951 (70-84), 1966 (74-86), 1958 (73-81-2), 1952 (79-75-1)

Median Seasons: 1967 (62-99), 1953 (59-95-3)

Top Five Players in fWAR: Bobby Shantz (16.9), Alex Kellner (16.4), Eddie Joost (14.6), Ed Charles (14.2), Ferris Fain (12.0)

Yes, the Athletics have three anti-dynasties in the top ten, and each one was worse than the last.

What’s so anomalous about the A’s history is that while they have had these three all-time losing stretches, they’ve also had several dynasties (or close) of the good kind (the 1910s, the ‘70s, the Bash Brothers, the Moneyball team if you go by the regular season). That’s how the franchise has managed to win 14 pennants (third in MLB history) and 9 World Series (3rd-4th) despite a losing record (9260-9766) overall.

1.Philadelphia Phillies, 1918-1948 (1187 points)

Total Record: 1,752-2,941-27 (.374, 61-win pace)

Total Runs: 19,797 scored, 25,593 allowed

Five Worst Seasons: 1939 (45-106-1), 1945 (46-108), 1928 (43-109), 1941 (43-111-1), 1942 (42-109)

Five Best Seasons: 1925 (68-85), 1918 (55-68-2), 1946 (69-85-1), 1929 (71-82-1), 1932 (78-76)

Median Season: 1934 (56-93)

Top Five Players in fWAR: Chuck Klein (34), Cy Williams (28.4), Jimmy Ring (20.4), Ray Benge (16.0), Virgil Davis (14.6)

This is where the scary music drops. One team’s ride of ineptitude towers over everyone else’s, to the tune of more than twice as many points as their next competition. Talking about this anti-dynasty is impossible to do without listing a bunch of factoids and oohing and ahhing at them, so here we go.

• Over thirty-one seasons, the Phillies averaged a 100-loss pace in a modern, 162-game season.

• They never finished higher than fourth, and never within single-digit games of the pennant.

• The latest in the year they ever had a share of 1st place was May 3, 1920, with a 9-5 record.

• The most games they ever were over .500 was 6 (8-2 in 1918, 12-6 in 1944).

• Their longest winning streak was 8 (1929).

• There’s only one 6-fWAR pitching season in this 31-year stretch (Raffensberger ‘44).

• If you split this anti-dynasty into two, with 1932 breaking them apart: the first one would finish third on this list with 524 points. The second would finish… first. It would be #1, and by a wide margin, at 667 points.

• If you added up entire franchises’ under .500 scores since 1901, only five others (Orioles, Athletics, Braves, Twins, Pirates) add up to more than 1187. That’s to say that for every other franchise, you could literally take their entire franchise history (since 1901 at least), and cherry-pick just the seasons where they finished under .500, and they still would not amass enough anti-dynasty points to top the granddaddy of all anti-dynasties.

So, how unbreakable is the Fightless Phils’ record? Given how few teams are on this list from recent years? It’s a lock. Consider that the Marlins have been losing since 2010, but they still are sitting on only 240 points, nowhere near making the top ten yet (and their anti-dynasty is in danger after a winning 2023 campaign). After the Marlins, the next-best active anti-dynasty is the Royals, and they’re only at 196. Teams just don’t run up the losing score enough, or nearly consistently enough, to seriously threaten a record like this one. Even with how horrible Oakland’s 2023 false swan song was- the fourth-worst record in the 21st century- the A’s would have to repeat that season eighteen times to pass the Phillies given where their anti-dynasty currently is (104 points). For the record, these Phillies finished with a worse winning percentage than the ‘23 A’s no less than six times.

People often debate whether it’s worse to root for a team who is consistently good but can’t win the big one, or to root for a team who is never good enough to make the big one. While I have sympathies for those who think the bridesmaids are the most painful to root for, there’s something to be said about having a team be this atrocious for this long. If you’re a Phillies fan in 1947, you’ve had all of the glimmers of opening-day hope beaten out of you so thoroughly and so early in the year for so long, that you would have to wonder whether you would ever live to see a good ballclub you can root for, let alone a champion. That must have made it ever sweeter in 1950, when the Whiz Kids really were able to not only post a winning season, but capture the National League pennant.