The most spoiled (and frustrated) teams (and fans) over the past 25 years

Some fans don't know how good they have it.

Earlier this week ESPN came out with another round of rage bait with their fan misery index, an attempt to measure which team’s fans have the most right to complain. In theory, I like the concept. Some fans are spoiled by their success of their teams and take it for granted, while others have not known a day of sports joy in years, and perhaps even decades, and have every right to be angry about it.

I just hated the results, mostly because they tried to tell me there were six fan bases in Major League Baseball that are more miserable than Pittsburgh Pirates fans.

Brother, that’s an insult.

Several of the teams that they concluded to be more miserable have won World Series titles in the past 20 years. By any definition those fan bases can not be more miserable than people stuck in Bob Nutting’s money stealing incompetence machine.

So I decided to take my own look at the most spoiled and miserable teams and fans across the four major North American sports leagues over the past 25 years.

Twenty-five years just seemed like a good time-frame.

It takes you back to the year 2000, a nice round year, and it’s a nice solid sampling of years.

Over 25 years there should be some reasonable expectation of seeing your team at least get close to a championship one time (or more), if not actually win one. Some teams win more over that time period. Other teams win less. Others win none at all.

It also covers a wide range of fandom. Older adults are far enough removed from the 1960s and 1970s where some teams (*cough* the Pirates *cough) found most of their success and it is no longer really relevant in the modern sports landscape, while young adults have had time to fully invest and go through the ups and downs of fandom. Everybody is living it right now.

It just covers a lot of ground to cut out recency bias, not overvalue things from 50 years ago (or more), and definitely not overvalue things from a time period where nobody has any memory of it or was even around for it.

My method uses a point system to try and add a level of objectivity to it and remove feelings and emotions. Everybody thinks their fandom is more miserable than everybody else.

My system gives teams 20 points for a championship, 10 points for appearing in a championship game/series, five points for reaching a semifinal/conference final/league championship series, three points for winning one round/game in the playoffs, two points for simply making the playoffs and losing in the first round/game, one point for a winning season that did not result in the playoffs, and zero points for a losing season.

I think this is a fair system. I think the results are fair.

Maybe you will disagree.

Maybe you will also have objections.

Championships get the most weight and should be weighted heavily. That’s the goal. Banners fly forever and all of that.

Appearing in a championship also has a lot of value. You get the experience and fun of going on that journey, and you do probably remember it, but you do not have the ultimate glory of experiencing the win.

Advancing in the playoffs is nice, but is easily and quickly forgotten if it does not produce a trophy.

This obviously does not take into account all elements of being a fan, like your general manager trading a beloved player, your owner being cheap or not doing more to win, the state of your stadium or arena or even actual big things like a team relocating (which is a very different level of misery). We are simply looking at team success here. Or a lack of team success.

Let’s start with the top-20 teams (out of 124 teams) on the spoiled side of the list.

The Spoiled Fans

1. New England Patriots: 183 points

2. Los Angeles Lakers: 146 points

3. San Antonio Spurs: 135 points

4. Golden State Warriors: 128 points

5. New York Yankees: 126 points

6. Miami Heat: 126 points

7. Boston Celtics: 117 points

8. Tampa Bay Lightning: 114 points

9. Boston Red Sox: 113 points

10. St. Louis Cardinals: 110 points

11. Pittsburgh Penguins: 107 points

12. Los Angeles Dodgers: 105 points

13. Kansas City Chiefs: 105 points

14. Houston Astros: 102 points

15. Philadelphia Eagles: 102 points

16. Pittsburgh Steelers: 95 points

17. San Francisco Giants: 90 points

18. Chicago Blackhawks: 84 points

19. Cleveland Cavaliers: 84 points

20. Baltimore Ravens: 83 points

Some thoughts on these teams at the top:

— Honestly, I think the system works. The Patriots are far and away at the top of the list, and with six Super Bowl wins and nine Super Bowl appearances over the past 25 years, they should be. I know they’ve stunk the past couple of years, but they could go winless the next five years and I still would not want to hear a single word of bitching out of anybody in their fan base. Frankly, that goes for the entire city of Boston and all of its sports teams. Boston has three of the top-nine teams here, and the Bruins are 24th. Seriously, if you ever hear a Boston fan complain about anything right now … well … I wouldn’t blame you if you closed a fist.

— The Lakers being in the No. 2 spot kind of surprised me, but I think that is where recency bias comes in given how mid they have been over the past decade. But with Shaq, Kobe and LeBron going back to 2000 they put four banners in the rafters of the Staples Center and played in two other NBA Finals. Championships matter. Same thing applies to the Spurs in the No. 3 spot. They might be going through it now, but for the better part of the 2000s and 2010s they were pretty much the Patriots of the NBA.

— The New York Yankees. Now we’re getting good. Nobody likes to tell you how tough they have it right now than Yankees fans because it’s been *checks notes* since 2009 that they won a World Series. Oh my God. The horror. THE HORROR. Let’s all pour one out for the long-suffering Yankees fans.

Here is the thing about the Yankees that makes them score so well here. While they may not have the championship success of some other teams (they still have two over the past 25 years — which is still a lot) they are ALWAYS good. They are NEVER bad. They are the only team in the big-four leagues that has not had a losing season over the past 25 years. They have made the playoffs 20 times in that stretch. Their longest postseason drought in this time frame is two years. It happened one time.

Going back further this team has not had a losing season since 1992. Not only do they always have winning records, not only do they almost always make the playoffs, they also generally advance in the playoffs when they get there.

There is a LOT to be said for being consistently good and competitive. If you are Yankees fan you know every April that you are still going to be invested and watching meaningful, important baseball through October. You are spoiled. You are not suffering. No baseball fan has had it better than you, consistently speaking, over the past 25 years.

Also there are 20 teams in Major League Baseball with a longer World Series championship drought than the Yankees at this current time. A 16-year wait is not that long. You only think it is because you are spoiled. SPOILED!

— The Cardinals just lurking there in the top-10 in a quiet, unassuming way totally tracks for their existence. I feel like nobody outside of St. Louis actually cares about them, but that team has played in four World Series, won two of them and appeared in six other NLCS over the past 25 years. An annoyingly consistent, successful franchise. I respect them, even if I hate it. And am jealous of it.

— Pittsburgh fans are going through it now because the Steelers have been consistently mediocre for a few years, the Penguins are into a rebuild and the Pirates are the Pirates. But from a big picture perspective, taking into account all teams, the past 25 years have been pretty damn good. The only other cities that have two teams appear in the top-20 here are Boston, Los Angeles and the bay area (San Francisco Giants and Golden State Warriors). The Steelers also kind of fall into the Yankees category of, yeah, YOU think your championship drought is a long time … but in reality, it is not. The playoffs have gone poorly, but every September you know the games in December and January are going to matter (even if you know the result) The Penguins rebuild is inevitable. Lean into it, trust the process and realize that for 15 years between 2005 and 2020 nobody in hockey had it better than you. Except for maybe Tampa Bay. Sometimes the piper has to be paid.

— Do we underrate the Miami Heat as a sports society? Maybe it’s because I’m only an NBA casual, but I feel like the Lakers, Spurs and Warriors all got their flowers over the years, but the Heat are right there with them in terms of overall dominance. That team has won A LOT. And won big.

— I honestly expected the Kansas City Chiefs and Houston Astros to be closer to the top-five, if not in it. But again … recency bias. Both teams have been the dominant team in their sport over the past eight years or so, but the years before this run were very thin for both franchises.

— The Cleveland Cavaliers! That is the LeBron James effect.

— The Chicago Blackhawks were so good and successful between 2008 and 2016 that it completely makes up for how bad they were from 2000-2008 and how incompetently awful they have been since 2016.

— The San Francisco Giants are a fascinating team here because they are a real quality over quantity team. Over the past 25 years they have made the playoffs just seven times. But those seven playoff appearances produced four World Series appearances and three World Series championships (all within a six-year span). They are the one team in the top-20 where I am not entirely sure of their placement. I almost feel like they could both be a little lower and a lot higher. I know the consistency is not there, but they had a legitimate mini-dynasty there.

Now, let’s take a look at the other side of this ranking and the most frustrated fans (as well as the full rankings for each individual league).