
The past two decades of Major League Baseball have seen the emergence of winners, feel-good rebuilds, and organizations that just cannot seem to win many games. Not just losing years, but sustained failure and repeated rebuilds. These are the franchises that have not been able to figure it out for a long period of time.
Honorable mention: Detroit Tigers
Detroit is riding the line closely but narrowly misses out due to their run between 2011 and 2014.
The depths they sunk to were truly ugly. A 43-119 season in 2003 still lingers. They endured seven losing seasons from 2000 to 2010, then rode out their competitive window and fell back into another extended losing spell with six losing seasons in a row from 2017 to 2022.
But this is what saves them:
From 2011-2014, the Tigers were among the best teams in baseball.
Detroit was not consistently bad. They were wildly inconsistent. When they were good, they
4. Colorado Rockies
The Colorado Rockies are the very definition of mediocrity. Rarely are they the worst team in the league. They just never matter.
Since 2010, they have had more losing seasons than winning seasons. They have also hovered between 70 and 80 wins for most of the last decade.
They have had no sustained run of dominance and no window of time where they felt like a real contender. The 2007 run was a true outlier.
The Rockies have spent 25 years just existing, between rebuilding and pretending not to rebuild, which is not a fun place to be in MLB.
3. Baltimore Orioles
Baltimore was not in a fast decline. Instead, they faded slowly and ended up in mediocrity for more than a decade.
They did have one glimmer of hope. From 2012 to 2016, they made the playoffs three times and won the division once. For a period of time, they were actually a contender.
Apart from that window, however, they spent the rest of this time getting stuck in cycles that never turned into anything concrete. Their recent resurgence and change in ownership can affect their current image, but it does not erase their years at the bottom.
2. Kansas City Royals
The Royals have the one component that all of the teams on this list lack.
A championship.
The three years from 2013-2015 were a real, deserved, dominant time in their own regard.
What else did they have? A lot of losing.
They had zero playoff appearances between 2000 and 2012, and once the championship arrived, they fell right back into old habits. The one championship saves them from being number one on the list.
1. Pittsburgh Pirates
Nobody is worse than the Pittsburgh Pirates.
They had a short period from 2013 to 2015 when it looked like they could be contenders.
And then things went back to normal.
There were no extended periods of contention, no deep playoff runs, and no championships to speak of to redeem their losing record.
While other teams on this list have instances where you can say "they really had a moment," Pittsburgh only had a flicker of something, and over 25 years, that is not enough.
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