Which MLB teams have wasted the most money since their last successful trip to the playoffs?

Recently, several of MLB's longest suffering franchises have ended long playoff droughts. The trend started somewhere around the time when the Reds got into the post season in 2010. Two years later the Orioles made it to the October dance as a Wild Card winner. Then the Pirates ended a string of 20 consecutive losing seasons in 2013 by kicking off a run of three straight trips (and counting) to the Wild Card play in game. The following year, the Royals ended the longest post season drought in North American professional sports and went to the World Series, and then this season the Blue Jays, Mets, Astros, and Cubs all smashed rather lengthy spans of futile baseball by making it to at least the LDS.

These results have turned the baseball world on its head. The combination of revenue sharing, regional TV deals, the importance of young players, and scouts' ability to better recognize future talent at an earlier point in the development process have resulted in an era of baseball where more teams can legitimately dream of winning the World Series in the near future than ever before.  In many aspects, this really has become the golden age of baseball.

But even in this remarkable period of baseball parity, there are still some clubs who just can't seem to get out of their own way, and in the process have spent hundreds of millions of dollars without seeing any playoff success. Let's identify them.

Below I have created two very similar tables. The first is a list of teams ordered by the total amount of money they've spent since they last won a playoff game. The reason I phrased it like this is because while MLB considers making the Wild Card play in game and losing a trip to the playoffs, there are many fans who make a pretty big distinction between a playoff trip that involves losing that game (and only that game) and getting to at least play in a best-of-five LDS.

So far, this playoff system has been in place for four seasons, giving us eight losers of these Wild Card games: the 2012 Rangers, the 2012 Braves, the 2013 Reds, the 2013 Indians, the 2014 Pirates, the 2014 A's, the 2015 Yankees, and the 2015 Pirates. That group of teams as a whole looks like a group with a satisfaction level much closer to teams who won 80 or more games and missed the playoffs than a group of teams who made the LDS.

For me, the most interesting team on that list is the 2013 Cleveland Indians. This is a group who technically ended a playoff drought of six years, but unlike the 2012 Orioles, the 2013 Pirates, the 2014 Royals, and the 2015 Astros and Cubs, they lost their Wild Card play in game and tend to get viewed differently around baseball circles. I'm not sure if this is right or wrong, but the difference is noticeable when it comes to conversations about teams who "turned things around".

So without further ado, here's the list of MLB teams who have spent the most money since their last playoff win (It's only 22 teams long because the eight teams to win a playoff game this season were left off it):

Note: (The figures calculated here were based on opening day payrolls. So technically some teams should have figures a little higher than this, but the general outcome / order will be the same)

In some ways, this is a view into baseball's new misery index. The Seattle Mariners now have the longest playoff drought in the sport, and fans of that organization have watched their team spend by far the most money without seeing any sort of playoff action of any kind. To top it all off, they're one of only two teams left in all of baseball to never go to the World Series (the Nationals being the other), so they get historical misery points here too.

Beyond that though, the list yields some unintended results. The Twins and Angels have hardly been model organizations in recent seasons, but piling up payrolls for teams who didn't win their Wild Card games also gets teams who got swept in the LDS in hot water on a list like this. The Angels posted the best record in the American League in 2014, but were also swiftly swept out of the playoffs by the Royals, so the last time they actually won a playoff game was all the way back in 2009.

Then the Twins really get the short end of the stick here. They've made the playoffs three times since last winning a playoff game in 2004, but were swept out of the LDS in 2006, 2009, and 2010. In total, Minnesota is on a 12 game playoff losing streak. They definitely deserve a spot somewhere on a list measuring some form of futility like this for not making the playoffs the last five seasons, but I'm not sure they should be as high as second.

One thing that I do like about this list though is that it punishes the Yankees for spending over $200 million for three consecutive seasons without winning any divisions or playoff games. While not as big of an advantage as it was in years past, the Yankee payroll is still an enormous head start for any club in a race to playoff success, and they've certainly squandered it in recent seasons. Their drought without a playoff win isn't nearly as long as some other teams listed here, but they absolutely should be leapfrogging some clubs with the resources they have. The apathy level from Yankee fans towards the club hasn't been this high since the early 1990's.

However, according to MLB, the Yankees did just make the playoffs this season. So let's see what this same list looks like if we amend the phrasing to say "how much money each team spent since last making the playoffs":

The Yankees and Pirates come off the list completely having been Wild Card losers in 2015, and the Twins, Angels, and Indians all move down (in a good way). The White Sox jump into the second spot having not reached the LDS since 2008, the Phillies move to third with their enormous payrolls and bad teams in recent seasons, and the Marlins, Padres, and Rockies round out the teams who have spent over $500 million since last playing a meaningful baseball game in October.

This is just one way to look at which teams are struggling and which teams have wasted the most resources, but it does provide an interesting snapshot at an interesting time with all the changes we've seen in MLB recently in terms of team success. The good news for fans of these franchises is that fortunes change quickly now in MLB. After all, the Mets and Royals are in the World Series, and who would have believed that was possible three years ago? I have a feeling that if someone where to make a list like this at the end of the 2018 season, it's going to look very different than it does today.

For now though, these are the teams who have burned through the most cash without seeing any playoff success, and the numbers are not pretty.