Are the Orioles the Biggest Losers Ever?

We need to talk about the Orioles. Yes, I’m stepping in to John’s territory here. As the Orioles beat was one he did not want anyway and this will be about how bad they are, and how good the Red Sox are, I don’t think he’ll object.

This post has actually come about because the Orioles are already 41 1/2 games behind the Red Sox. Tom wanted to know the furthest behind a team has ever been at the end of the season; naturally I (with the usual help from Baseball Reference) am going to oblige. This is incredibly unlikely to continue – the Orioles already won a game against Boston between when Tom first posed the question and now – which makes it all the more imperative that we answer the question before it becomes irrelevant. Are the Orioles on track to finish the most games behind in baseball history?

Before we get deep into the stats, there is an obvious answer, which some of you may already know. The 1899 Cleveland Spiders are notorious for being the worst major league team ever. With a record of 20-134, they finished 84 games behind the Brooklyn Superbas and posted the lowest winning percentage ever, .130.

There were extreme mitigating circumstances, which you can read about in plenty of places. The short version: the Spiders’ owners, brothers Frank and Stanley Robison, also bought the St. Louis Browns and traded all of Cleveland’s stars (including Cy Young, who may also be familiar to some) to St. Louis. The Spiders unsurprisingly went on to post that squalid record and their ineptitude even forced them to play the majority of the season on the road: because their attendance was so low, other teams did not receive enough money from ticket sales to cover expenses and refused to make the trip.

The Spiders therefore don’t really count, both for this reason and the fact that the American League didn’t even exist until 1901, and the World Series was first played in 1903. Pre-1900s baseball organisation was constantly in flux, with leagues and teams regularly created and destroyed, and poor regulation allowing for shenanigans like those of the Robison brothers. It’s also less interesting: even if the Orioles lost all of their games the rest of the way, they wouldn’t be as bad as the Spiders by winning percentage, and the Red Sox would have to be a 114 win team to put them more games behind.

We’ll instead focus on records since the American League was created. Fortunately Baseball Reference makes it particularly easy to find every team’s record since 1901. I then calculated the difference in both winning percentage and total wins for the best and worst teams every season.

The Orioles have a .284 winning percentage, putting them on pace for 46 wins, while the Red Sox are a .689 team, a 112 win pace. Let’s find out how they stack up. With a number of ways to slice this, given the repeated changes to baseball’s structure, there are a few different answers to the question. First up, the biggest difference regardless of league or division.

Biggest Difference, All Teams:

1909: Pittsburgh Pirates (110-42, .724) – Washington Senators (42-110, .276): .448 W% Difference, 68 games back

The 1909 Pirates are the third-best team of all time by winning percentage, winning the NL over the luckless 104 win Cubs, fresh off what would be their last World Series victory for 108 years. They followed through on that dominance by winning the World Series – just – against the Tigers, 4-3.

They were led by Hall of Fame shortstop Honus Wagner, who was worth more than 9 wins on the back of his .339/.420/.489 line, good for a 177 OPS+. That was only the fourth-best mark of Wagner’s career: the year before he put up a 205 on his way to 11.5 bWAR. This would be Wagner’s only World Series win; it’s much harder to make the Fall Classic when only the top team in each division gets in.

The Senators, who would become the Minnesota Twins over 50 years later in 1961, managed to lose 110 despite having one of the greatest pitchers of all time on the roster: Walter Johnson. The 21-year-old Johnson was not yet at the peak of his powers, with his true breakout coming the year after when he compiled 370 innings of a 1.36 ERA. Nonetheless, he was comfortably the best player on a woeful team.

Washington were bad on both sides of the ball but especially offensively, where they did not have a player of Johnson’s calibre, and scored a full run less per game than the league average. They finished with just 382 runs scored over their 152 games, 284 runs behind the AL-leading Tigers.

An honourable mention also goes to the 1904 Senators, who finished 68 games back of a different team, the 106-win New York Giants. They had an ever-so-slightly smaller winning percentage gap of .441.

How the Orioles and Red Sox compare: There is a 43 point gap in winning percentage now. With the two teams on pace to have a 66-win gap, they would finish two games behind the 68 wins here. The Pirates and Senators would have won 117 and 45 games respectively over a 162 game schedule, so that is a gargantuan 72-win difference, difficult for either to manage even with the current deficit.

Biggest Difference, Within League:

1906: Chicago Cubs (116-36, .763) – Boston Beaneaters (49-102, .325): .438 W% Difference, 66.5 games back

The 1906 Cubs even surpass the 1909 Pirates. They are the best team of all time by winning percentage and it’s not that close, beating the second-place 1902 Pirates by 22 points (Cubs and Pirates fans, get yourself a time machine and get back to the early 1900s). This Cubs roster was not short on Hall of Famers. Many students of baseball history will know the infield trio of Joe Tinker, Johnny Evers, and Frank Chance, immortalised in the poem “Baseball’s Sad Lexicon“. All were among the Cubs’ most valuable players that season, with Chance and his 158 OPS+ leading the way. This was a great team from top to bottom, with Chicago able to field almost an entire starting lineup and rotation of above-average players.

Ace of the staff Mordecai “Three Finger” Brown joined that infamous infield in the Hall. While this was not his most valuable season – both 1908 and 1909 surpassed it – the ERA was the gaudiest, at a jaw-dropping 1.04. Even for the dead-ball era, this was a stunning performance, still ranking eighth all-time by ERA+. The unheralded star of this team, however, was Harry Steinfeldt, a 28-year-old third baseman who had the best season of his career, almost matching Chance with the bat. Steinfeldt would never again reach the heights of 1906 and the Cubs would go on to lose the Series to the White Sox, a team 23 wins inferior. Both Steinfeldt and Chicago would make up for it with back-to-back titles in the subsequent years.

The Beaneaters (later the Doves, Bees, briefly the Rustlers and now much better-known as the Atlanta Braves) were just as hapless as their cross-town rivals the Americans, who would become the Red Sox just two years later. Both teams won just 49 games, although the Americans would lose three more and actually also finished 68 games back of the best record, saved from the first category on this list only by virtue of a slightly smaller winning percentage gap.

While the Beaneaters weren’t as bad as the 1909 Senators, they did have an even worse Pythagorean record than their actual performance at 45-106. They used Al Bridwell and his .548 OPS at shortstop almost all season, and they were essentially given no choice: the bench was even worse. The team also made 337 errors in the field, averaging more than two per game. Poor Gus Dorner was left to suffer for 273 1/3 innings at the back of the rotation, losing 26 games and posting the league’s second-worst ERA.

How the Orioles and Red Sox compare: The winning percentage gap looks a little more attainable at .438, 33 points ahead of their current margin. The 71-win gulf on a 162-game basis still makes it seem incredibly unlikely, though. The 1906 Cubs were a 124-win team over that many games, a number that is almost impossible for Boston to get to already. The Orioles, however, can certainly win less than the pro-rated 53 for the Beaneaters.

Biggest Difference, Within Division:

1998: Atlanta Braves (106-56, .654) – Florida Marlins (54-108, .333): .321 W% Difference, 52 games back

It might have become clear that everything so far happened a very long time ago. There are a lot of reasons for that, including more disparate resources and a lack of mechanisms to ensure greater parity. Once divisional play was introduced, there were fewer teams involved in the games back calculation, and some of those mechanisms had been introduced, such as the draft. Talent also flooded the game in myriad forms, from the breaking of the colour line to the development of farm systems and a much more comprehensive scouting network.

That’s a long way of saying that no teams have got anywhere near our leaders in the first two categories in the divisional era. The team that did fall far enough behind wasn’t the 2013 Astros, or the 2003 Tigers, but it was a team you might expect. It may well have been the team that you guessed: of course it’s the Marlins. Only the Marlins could come off a World Series win and post one of the worst seasons in history. It is the only time a team has won the World Series and finished last with 100-plus losses the following year.

It was Wayne Huizenga, not Jeffrey Loria, who instigated the fire sale following the 1997 Series win, trading stars such as Moises Alou, Gary Sheffield, and Kevin Brown. The new-look squad did not feature a single above-average starter, with a pitching staff that collectively produced a 5.18 ERA, 22 percent worse than league average, walking a batter every other inning and giving up 10 hits per nine.

The Braves could not have been more different: they led the league with a 3.25 ERA, a quarter of a run better than second place, with one of the best pitching staffs of all time. Greg Maddux, Tom Glavine, and John Smoltz carried the rotation to that stellar ERA, while Andruw Jones and Chipper Jones each put up seven-win seasons. Andruw was at the peak of his powers in the outfield as a 21-year-old, while Chipper mashed his way to a .951 OPS. Andres Galarraga launched 44 bombs and even catcher Javy Lopez got in on the act with 34 homers. This Braves team lost the NCLS to the Padres and somehow would only win one World Series title despite winning the NL East 14 times in 15 seasons from 1991 to 2005.

How the Orioles and Red Sox compare: They can do this! The margin even allows for a fair amount of regression the rest of the way. Boston could fall off to be a 100-win team, a winning percentage of .617, and Baltimore would still be the most games back of any team in the divisional era. If the Orioles significantly improved the rest of the way to a .383 clip (it sounds ridiculous to say ‘significantly’ but it is 100 points higher than their current record) to finish at 52-110, Boston would have to become the first team since the 2005 Cardinals to win 105 games in order to break the record.

Unlike the rest of the modern teams, in fact, the current gap does stack up well against those older, larger margins. The current winning percentage difference would rank eighth all-time, and if they stayed on the same pace that 66-win gap would be fourth-largest all time.

This is as much about Boston being excellent than it is Baltimore being terrible: the Orioles currently have the 15th-worst winning percentage since 1901, while the Red Sox are 16th-best. It takes two to make this record come together and despite the huge gap right now, they’re still not on pace to set the all-time record. All it takes is either team to regress back towards the mean a little and this will start to fall apart. Nevertheless, the Orioles are on track to lose a division by more than any other team in history, and it’s not all that close.

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