What would you change?

Methodology

For a single season, a team's heartbreak score is broken down into three parts—their win-loss record, their DVOA, and their playoff run.

Win-loss record is easy: the more games you win in the regular season, the more painful it is to not come away with a championship. Teams earn points based on how far above .500 they were in any given season, with a perfect season getting 100 points and an 8-8 year getting 0. Specifically, it's (win-loss percentage - 0.5 * 200). Last year's Bengals went 10-7 for a win percentage of .588, giving them 17.6 heartbreak points. The 13-4 Packers got 52.9, the 9-8 Eagles got 5.9, and so on and so forth.

DVOA is easy—the better your team was, the more painful it is to not come away with a championship. That, too, is simple. We take a team's positive DVOA, capped at 50%, and multiply it by 200. Last season's Bengals actually had a slightly negative DVOA, but we don't penalize them for that. There are no negative heartbreak points as that would imply that a team would be pleased for some reason that they didn't win a Super Bowl. But the league-leading Cowboys' DVOA of 30.9% earned them 61.8 heartbreak points; a dominant regular season leads to more pain when you eventually collapse. For 1950 to 1980, we use Andreas Shepard's Estimated DVOA, and for 1920 to 1949, we use SRS-to-DVOA conversions.

Playoff run points are more complicated. They are based on two assumptions. First, losing deeper into a playoff run should hurt more. All things being equal, it hurts to lose a Super Bowl more than it hurts to lose a wild-card game. Secondly, it hurts more to lose a close game than a blowout. Bills fans are pained more by Scott Norwood hooking his field goal wide right than they are from the Cowboys blowing them off the field two years later.

Teams thus get points for how deep they went in the postseason, modified by how close the game actually was. A Super Bowl loss is worth between 100 and 200 points, a conference championship loss is worth between 50 and 100, a divisional round loss is worth between 30 and 50, and a wild-card loss is worth between 0 and 20. You get the full value if you lose by one point or in overtime. You get the minimum if you lose by more than 20 points. A more accurate system would take into account if the losing team had the ball with a chance to score at the end of the game, or if they padded the point differential with garbage-time points and so on and so forth, perhaps taking into account average win probability over the course of a matchup, but the play-by-play data needed to do that simply isn't available for the majority of NFL history. To keep everything on a fair playing field, we're just linearly sliding down by margin of defeat. The Bengals earn 180 heartbreak points for their 23-20 loss in the Super Bowl, which gives them 197.6 heartbreak points for 2021 when combined with their other points. By comparison, the Cowboys' wild-card exit only earned them 14.0 heartbreak points. So even though they were the better team than the Bengals for the regular season, their 2021 only picked up 117.0 heartbreak points. Playoff failures are what stick in the memory and are the most important part of any heartbreak rankings.

The perfect season would earn 400 points—an undefeated regular season, a DVOA over 50.0%, and the closest possible loss in the Super Bowl. That has never happened, but the 2007 Patriots managed to score a 390 when the Giants knocked them off in Super Bowl XLII. That comes out as the most painful individual season in this system, joining the 1942 Bears, 1968 Colts, 2001 Rams, 1948 Cardinals, and 1990 Bills as the only seasons worth 300 points or more.

But we're not interested in single-season heartbreak. It sucked for Patriots fans that they lost in 2007, but they won Super Bowls on both sides of that loss. The Bears won plenty in the 1940s, the Colts rebounded from Super Bowl III to win Super Bowl V, and so on and so forth. While those seasons sucked in the moment, we have to take into account all the success that happened around them in order to truly judge how painful an era was. Even the most painful Super Bowl defeat is somewhat soothed by a full trophy collection.

Each championship a team wins radiates out heartbreak-soothing rays, diminishing the pain of any lost years around them. One year removed from a Super Bowl win in either direction knocks off up to 400 heartbreak points. Two years away removes 200 points, three years 100 and four years 50. Those stack, too—the 2002 Patriots season, bookended by three Super Bowls, has a 1,000-point penalty, because no one feels bad that New England didn't win four out of four Super Bowls. With these penalties included, the 1990 Bills season becomes the most painful in NFL history; all the other notably painful years had championships around them which counteract some of the heartbreak.

Yes, this means that a season can become less painful retroactively, but I think that makes sense. If the Bengals win the Super Bowl in 2022, 2021 will be looked back at as a building year and a learning year, and an important step on the way to their eventual glory. If they don't, it's a horrendous missed opportunity, but only time can provide the proper context!

To calculate a team's score over multiple years—which is how we're ranking them here—we use a weighted system. A team's run starts the first year they would earn points before the championship penalty. It ends when they either have back-to-back non-scoring seasons (either a losing record, or a .500 record with a negative DVOA) or they win a championship. Their total score is computed by summing 100% of their heartbreak score for their best season, 95% for their next-best season, and so forth. This prevents a team from just compiling wild-card losses and pretending that's as bad as a Super Bowl loss, a way of balancing both breadth and depth of heartbreak.

That leaves us with 44 Heartbreak Dynasties, 44 runs of teams that earn at least 400 points. We're going to spend the next couple weeks counting them down and celebrating, and at the end, we'll declare which team in which era caused the most pain. We're keeping the final list secret until the end because we're not making distinctions between quantity and quality at this time around. I have a sneaking suspicion certain fan bases may be able to predict the names at the top.