The Kings of Pain

Some seasons are more painful than others. (via John LaRue)

Much was made of baseball’s championship droughts in 2016. That was the case all season long because of the Chicago Cubs’ success, but the drought discussion doubled down when Cleveland sprinted through October to face the Cubs in the World Series. For most baseball fans, one significant drought or another has been in the national psyche for all of their lives. First, it was the Red Sox prior to 2004, then the lesser-known White Sox drought through 2005, followed by the Cubs and Cleveland.

That’s a lot of pain to go around for fans. I want do the impossible. Let’s quantify that pain, and put a number on it. Perhaps a reductionist approach can soothe some of the torture. And then we can determine which teams’ fans have endured the most pain during their respective droughts.

First, let’s establish some ground rules for how fan pain is going to be interpreted. Let’s begin by asking “How many more games did a team need to win to finish the season as World Series champion?” A team that lost in six games in the World Series needed two more wins. A team that lost in Game Seven of the League Championship Series (or Game Five prior to 1985) needed five more wins. A team that got swept in the League Division Series needed 11 more wins. And teams that finished three games out of first place prior to the Wild Card era needed 11 more wins (1985-1994) or 10 more wins (1969-1984). Before the LDS began in 1969, any team within six games of first place in its league can claim that it could have won a World Series by amassing between six and 11 more wins.

Using those criteria, points — pain points — are assigned based on how many more wins were needed. The idea is simply that the closer you get without sealing the deal, the more it’s going to hurt. Getting swept in the World Series is bad, but that particular team was really never close to actually winning it. Losing in the decisive seventhh game, however, means you were 27 outs or less from bringing home a winner, a much more painful scenario. Here is how the point system breaks everything out:

But there’s more to fan pain than postseason failure. Any season that ends outside of the playoffs is going to accrue pain. There’s an inverted U in fan pain by my logic, based on the number of games back your team finishes. Finishing close is more painful because it evokes a woulda-coulda-shoulda longing. Finishing further out is also more painful, as it comes with a side dish of shame and embarrassment. In the middle, in the 10 to 19.5 games back level, there’s only mediocrity — frustrating, to be sure, but not as painful as the other extremes. With that in mind, I’ve used the following math to quantify your pain:

There are a few other conditions that can incur pain. After all, not all postseason failures are created equally. Here are some other conditions:

Losing a decisive final game of a series is doubly painful, so more pain points are awarded when that happens. Losing Game Seven of the World Series gets you three additional pain points on top of the 11 that you already earned by falling one win shy of a championship. Losing Game Seven (1985-present) or Game Five (1969-1984) of the LCS earns you two points. And losing Game Five of the LDS is worth one point.

There are also teams that have lost one-game playoffs to reach the postseason. That’s worth a little pain — 1 point, in fact. It’s not going to incur too much stress, as you still needed to win between four and 11 more games to become World Series champ had you won the one-game playoff. But it’s still worth a little pain. I’ve opted to treat the recent Wild Card game in this same way, with equal pain for a loss as you would get from a one-game playoff loss.

And last but not least, you get two points of pain if you lost a playoff series in which you held a two game lead. That’s an especially tough situation because you had started to brace yourself for a series victory, especially in the three-games-to-one lead scenario, only to see it evaporate over two or three days.

Once your team wins a World Series, your pain clock resets to zero. All of the painful moments you witnessed prior to the title suddenly morph into a merit badge. “I endured Buckner and Bucky Dent to get to this moment.” And then the pain begins anew. The same holds true for a franchise that moves. Very few Nationals fans have followed the franchise all the way from Montreal, nor do O’s fans still feel the burn of the franchise failures when they were the St. Louis Browns. Once a team moves, the pain ends in the old city and it begins at zero in the new city.

Plugging all of the numbers in for every franchise, let’s look at the 10 franchises that subjected their fans to the most pain before a World Series victory or the franchise mercifully moved, ending the anguish.

No. 1: Philadelphia Phillies, 311.3875 Pain Points, 1903-1979

Before the Curse of the Bambino, before the billy goat and Bartman, before the famed droughts in Cleveland and Chicago’s South Side, there was an epic drought in Philadelphia. And using our formula, it takes the top spot by a resounding 55 points of pain. And our point system doesn’t even acknowledge the 1964 collapse. The stretch from 1938 to 1945 was particularly cruel to Phillies fans. The franchise drought was punctuated by seven finishes of more than 50 games back from 1903 to 1979, including every year from 1939-1942, plus 1945 for good measure. It also had 10 more finishes between 40 and 49.5 games back during the 77 years. The cherry on the sundae was two World Series losses and back-to-back-to-back NLCS defeats from 1976 to 1978.

What made this drought especially frustrating for fans wasn’t the postseason failure. In reality, none of the postseason losses by the Phillies were especially close, which minimized the pain. In fact, prior to 1980, the Phillies had won just three postseason games since the inception of the World Series in 1903. The bulk of the pain for Phillies fans comes from just plain ineptitude. Congratulations, Phillies fans 50 and older. You endured more pain than any other franchise.

No. 2: Boston Red Sox, 255.995 Pain Points, 1919-2003

Unlike the Phillies drought, the bulk of the pain in Boston comes from postseason failure. And not just run of the mill postseason failure, but failures at the most painful levels. The Red Sox lost four decisive World Series Game Sevens, including one that saw them blow a two-game series lead. They also lost a decisive Game Seven in an ALCS, lost two one-game playoffs, and absorbed five other postseason failures along the way. The Sox peppered their postseason failures with 10 finishes of 40 or more games back, with three of those (1927, 1930, and 1932) crash-landing at 50 more more games back.

The pain amassed by older Red Sox fans was truly a rich tapestry, with virtually every kind of pain merit badge imaginable foisted upon them. It would have been far too difficult to objectively capture specialized ignominy like the Ruth trade, the massive success of their rivals, Bucky f’in Dent, Enos Slaughter’s mad dash, or Bill Buckner, across all franchises. But those events add significant fuel to the Sox drought. In other words, as painful as the Sox’ 255.995 pain points were, it was even more painful in reality.

No. 3: St. Louis Browns, 246.725 Pain Points, 1903-1953

This drought didn’t so much end as it received a mercy killing when the Browns took off for Baltimore for the 1954 season. In at least one way, it’s the most impressive pain threshold on this list because it all occurred in an extremely compact time frame. The Phillies took 77 seasons to reach their total, and the Red Sox had 85. The No. 4 Cubs needed 107 years. For the poor Browns, it was merely 51 years. Amazingly, they reached only one World Series in that time, and had only two seasons in which they were 11 wins or less away from a championship. The Browns were one of just five teams total to crack the 4.0 pain points per year barrier during a drought of 20 years or more:

The Browns’ 246.725 points of pain is almost exclusively gained from massive ineptitude. One out of every three seasons for the Browns ended 40 or more games back. They racked up 50 games back or more six times. The most memorable franchise moments were Eddie Gaedel’s at-bat and Grandstand Manager’s Day, which should probably tell you everything you need to know about the quality of the product on the field.

No. 4: Chicago Cubs, 245.1875 Pain Points, 1909-2015

Had Cleveland won Game Seven this year, the Cubs would have rocketed up to No. 2 on the list. Something tells me Cubs fans are perfectly okay with missing out on that experience. The Cubs have the longest drought by far on this list, enduring 107 seasons in between championships. Their pain point total was suppressed by a lack of World Series pain since 1945, avoiding the highest levels of postseason pain.

Additionally, of the franchise’s 14 postseason trips during the drought, eight ended with one postseason victory none. They didn’t give themselves many opportunities for postseason glory, and the few that they had still left them almost as far away from a title as a team that didn’t make the trip in the first place.

The Cubs pain is also suppressed by a lack of truly awful seasons. Unlike the Phillies, Browns and Red Sox, the Cubs never finished 50 or more games back, and have only two seasons finishing more than 40 games behind.

As with the Red Sox, however, a significant amount of frustration can’t be captured objectively. The 1984 and 2003 squads famously added pain by blowing a two-game series leads in the playoffs, but that doesn’t account for the way they blew those leads — Leon Durham’s error in ’84 or the 2003 meltdown in Game Six. Additionally, a certain level of misfortune comes with the statement “We haven’t won a World Series since the Ottoman Empire existed” or 70 years without even reaching the World Series.

My objective measures show the St. Louis Browns with more pain, but I would understand if Cubs fans wanted to rank their pain higher.

No. 5: Brooklyn Dodgers, 217.825 Pain Points, 1903-1954

The Dodgers’ drought is most comparable to the modern Red Sox drought, nearly matching the Red Sox’ diversified portfolio of pain move for move. In the 52-year drought, the Dodgers exposed their fans to seven World Series losses, two World Series losses in a decisive Game Seven, two one-game playoff losses, nine seasons of more than 40 games back, and four seasons more than 50 games behind. The only difference between the Red Sox and the Dodgers is the lack of a blown two-game series lead in Brooklyn.

It all mercifully came to an end with their seven-game victory over the Yankees in the 1955 World Series, but the wound was permanently ripped back open just two years later when the franchise departed for Los Angeles. Perhaps most impressive about the Dodgers’ drought is that, as with the Browns and a few others on this list, it came in such a compact time frame. Those 217 points of pain represent a lot of suffering for a stretch of five decades.

No. 6: Chicago White Sox, 196.165 Pain Points, 1918-2014

The Pale Hose didn’t struggle as much as their Windy City neighbors, but their 87-year drought ranks as the second longest in major league history. It surpasses even the infamous Red Sox stretch. A lack of World Series appearances (only two from 1918 to 2004) kept the White Sox away from serious postseason frustration.

There also weren’t very many LCS or even LDS losses in between World Series titles. The White Sox’ entire postseason appearance list during the drought includes 1919, 1959, 1983, 1993 and 2000. None of those appearances featured a decisive Game Seven (or Game Five), nor did they blow a 2-game series lead.

The bulk of the White Sox pain derives from two years of 50-plus games back, seven years with 40-plus games back, and a giant bucket full of playoff-free seasons. The missing pain in this equation is obviously the Black Sox scandal and the banishment of Joe Jackson from the Hall of Fame. That said, I’m not sure how much a White Sox fan in 2004 was suffering over Shoeless Joe and the Black Sox.

No. 7: Cleveland Indians, 159.9675 Pain Points, 1949-Present

We finally find our first active streak on the list, fresh off of the most painful season ending — in terms of our pain points — in franchise history. Most of this drought has been fairly harmless for Cleveland. Of the 68 years in the drought, 20 fall in the 10-to-19.5 games back category. Only three seasons eclipsed the 40 games back barrier, cresting at 47 games in 1969.

That said, Cleveland baseball fans have been pummeled since the mid-1990s. Their four most painful seasons in franchise history have happened since 1995 (1995, 1997, 2007 and 2016). In fact, 30 percent of all the pain has happened since 1995. They’ve played in six World Series and three have been since 1995. Two ended in Game Seven losses, this year featuring the bonus of a blown two-game series lead. For perspective, if the Indians’ last championship had been in 1990 — meaning the current drought points had accumulated only since 1991 — they would rank fifth among all active drought points, with Cleveland’s total collected in just 26 years.

No. 8 Philadelphia Athletics, 137.06 Pain Points, 1931-1954

The A’s represent the second team on the list to end the fan suffering by moving, in this case to Kansas City for the 1955 season. The A’s won back-to-back championships in 1929 and 1930, and a year later were a win away from becoming baseball’s first three-peat champs. Then the bottom swiftly fell out. But in a 13-year span from 1934 to 1946, the A’s never finished better than 17 games back. From 1936 to 1939 was an especially woeful stretch, with finishes of 49, 46.5, 46 and 51.5 games outof first place.

The first and last seasons of the drought made for painful bookends. It began with a loss in a decisive Game Seven in the World Series. It ended with the A’s saving the worst for last, finishing a whopping 60 games back in their final season in Philadelphia. That stretch for the A’s is one of just five droughts of 20 years or more to crack the 4.0 pain points-per-year barrier, including three other teams on this list. In fact, the A’s drought is the only one to crack 5.0, registering the highest at 5.71. (see previous graph from the Browns section)

No. 9: Washington Senators, 136.595 Pain Points, 1925-1960

Here’s another franchise whose drought ended only because the franchise moved, with the Senators shipping off to Minnesota. The streak featured two World Series losses, including one in a decisive Game Seven after the Senators had a two-game series lead in 1925, the drought’s first year.

But the bulk of pain came from finishes of 40 games back or more. These Senators averaged a finish of 40 games out or more every five years during the 36-year drought. Their best finish in the last 15 years of that run was 17 games back. From 1934 to 1960, the Senators finished fewer than 10 games back just once. There’s a reason the Senators were the lost cause benefiting from a Faustian deal in Damn Yankees. This drought firmly established them as the nation’s lost cause.

No. 10: Boston Braves, 135.0875 Pain Points, 1915-1952

Our top 10 rounds out with yet another team whose torture of its fans ended in a move, this time to Milwaukee. The Braves won their only Boston World Series in 1914, ending an extremely painful stretch. The 10 years prior to that 1914 championship had seen seven finishes of 50 games back or more, good for 99.95 pain points in one awful decade of baseball. Then the franchise inflicted another 135.0875 pain points on its before departing for Milwaukee.

The core of the 1914 champs — Johnny Evers, Rabbit Maranville, Red Smith, Joe Connolly — finished a respectable seven and four games back, respectively, in 1915 and 1916. Then the core began to dissolve and the Braves quickly sank to the bottom of the standings. From 1917 until 1947, they never finished better than eight games out of first place. The most shame was amassed during a 1935 season that placed them 61.5 games back. Thanks to six other 40-plus games back finishes and a six-game World Series loss in 1948, the Braves climbed these rankings before putting Boston fans out of their misery and moving to Milwaukee.

Active Droughts

Since October 2004, the three most famous droughts in recent baseball history — Boston and the two Chicago franchises — have ended. That leaves Cleveland as the only team with an active streak in the top 10, making that franchise the current King of Pain.

However, a few more franchises are slowly creeping up the list. Houston registers 121.65 pain points, good for the 11th longest streak of all time. The Astros are a World Series Game Seven loss away from reaching the top 10. The Padres have the third highest current drought at 100.125, but their slow burn pace makes them unlikely to reach the top 10 any time soon.

From there, it falls off rather quickly to Milwaukee (89.295), Texas (83.885), Pittsburgh (81.2725), Detroit (77.775) and Seattle (75.55). The Brewers, Rangers and Mariners are still seeking their first World Series championship to eradicate their aggregate pain. In Detroit and Pittsburgh, it’s been 32 and 37 years respectively since tasting champagne and each team has populated its drought liberally with stretches of awful baseball and a few torturous near-misses.

Still, barring a 20-year stretch resembling what Cleveland has gone through since 1995, none of those five teams is likely to crack the top 10 any time soon.

References & Resources

• Baseball-Reference