5. The Colorado Rockies are a dumpster fire
This is the easiest spot on the list by a wide margin as the Rockies' front office has a strong argument for being the worst in all of baseball. Year after year, the Rockies make decisions that make baseball fans everywhere go "what the hell are they thinking?".
While the bulk of the damage done to the Rockies was done under the previous leadership of Jeff Bridrich, the current iteration of the Rockies' front office has done little to make things any better. The Rockies won just 68 games last season and it looks like they will fail to win that many this season as they currently sit at 49-84 and in last place in the division yet again.
It isn't just wins and losses as the problem here although that has certainly been ugly. The marquee move that this Rockies front office has made was signing a way past his prime and beat up Kris Bryant to a seven year, $182 million when NO ONE thought that he should get that much money or that many years. In two seasons with the Rockies, Bryant has played in a total of 107 games with a .770 OPS.
The draft classes have been suspect at best, the front office has done little to try and improve the roster, and their player development has had mixed results at best especially when it comes to pitching (Coors Field hasn't helped there). Colorado has earned their spot at the bottom of this list for sure.