NFL: Cleveland Browns

Since the “new” Browns returned in 1999, they’ve gone 54-106 with only one playoff appearance and a litany of terrible decisions for their trouble.
This is the franchise that drafted Tim Couch... thought Butch Davis was going to be a legit NFL coach... couldn’t even make the playoffs despite going 10-6 in 2008... gave Romeo Crennel a two-year extension... and hired Eric Mangini.
Braylon Edwards has the dropsies, Brady Quinn is headed for bust-ville, Donte Stallworth is in just a little bit of legal trouble, and apparently, their facilities are a festering pile of human disease, since the Browns lead the league in
staph infections.
NBA: Los Angeles Clippers

The Clippers are so historically inept, trying to list their foibles over the years would take up way too much space. So let me point you to Bill Simmons’
astonishing breakdown of how amazingly awful this franchise has been over the years.
Not only are they second-banana L.A., they're number two in their own arena. Their owner is a racist cheapskate, they have
a permanent spot reserved at the draft lottery, their players suffer catastrophic injuries on a regular basis, and people would rather
screw their friends over than re-sign with the team.
About the only good thing you can say about the Clips is that if you’re ever in L.A. and want to see an NBA game, there are plenty of good seats available.
MLB: Washington Nationals

The Nationals may be new, but they’ve got a long history of ineptitude in their former incarnation as the Montreal Expos - the team that Major League Baseball had to run for three years because no one else wanted to.
Moving to D.C. was supposed to lift the Expos/Nats out of the doldrums, but nothing of the sort has happened. Washington has been terrible, finishing no higher than fourth in its four full seasons. And they're currently on pace to finish with the worst record in MLB history.
Not to mention that their former GM, Jim Bowden, is under investigation by the FBI for skimming bonus money from unsuspecting Latin players. And the building of their stadium was a public fiasco. They can’t even get their
damn jerseys right.
NHL: New York Islanders

The Isles may have had some glory days back in the 1980s, but that was a long time ago. In a very different NHL. Now, the Islanders are the laughingstock of the league, playing in an obsolete arena with an owner who regrets buying the team.
While other bad NHL teams at least have promise (or at least the option to move to greener pastures), the Islanders are stuck playing in their decrepit building while forced to trade away any halfway decent player they get because of money woes.
A parade of coaches, GMs and current stars, have set up shop with the Isles only to be fired/bolt as soon as possible. Even trying to change their image with
new uniforms proved to be an unequivocal disaster.