Houston AstrosCurrent Record: 33-69
Last Winning Season: 2008
Last Playoff Appearance: 2005
Last Place Finishes Since 2000: 0
The Astros make this list primarily because of how bad they are this year, as they have the worst record in baseball by far. To put it in context, the Astros have 33 wins, while every other team has at least 40. The last two years Houston has defied the odds and made it to mediocrity, but this year they've fallen off the cliff. Check out the roster and see how many players you've actually heard of. Exactly. Hunter Pence has to be treated as a franchise player even though he's not because the fans would revolt. The farm system isn't exactly full of top of the line talent either. Short term it's going to hurt. What the Astros have going for it is a recent history that beats these other teams (that World Series appearance was a mere 6 years ago), and a new owner coming in. Astros fans know that Drayton McClane and GM Ed Wade are disasters. The hope is that Jim Crane and whoever he hires as GM can put the team on the right track after years of rot.
Baltimore OriolesCurrent Record: 40-58
Last Winning Record: 1997
Last Playoff Appearance: 1997
Last Place Finishes Since 2000: 3
I have personal experience with the disaster that is the Baltimore Orioles. The most damning evidence against them is the about to be 14th consecutive losing season. If the Pirates hang on and finish above .500, the new current record for consecutive losing seasons heads south to Camden Yards. Only the Devil Rays kept the Orioles from a bunch of last place finishes, which is of course ended when the Rays got good. This year there was optimism thanks to manager Buck Showalter and four young starting pitchers: Brian Matusz, Zach Britton, Chris Tillman, and Jake Arrieta. Of those four, only Arrieta is still in the majors. Matusz has essentially been injured all year, Tillman's fastball has disappeared, and Britton was sent back to AA to get away from the stink that is the big league clubhouse. The young hitters also have stagnated since coming to Baltimore. Adam Jones? Still a decent power, low OBP guy. Matt Wieters? He might be the best defensive catcher in the league, but his .733 OPS isn't "Mauer with power." Veteran stopgaps Vlad Guerrero and Derrek Lee have been disasters, continuing a tradition of older players coming to Baltimore to tank.
There has been one constant in this decade and a half of failure: Peter Angelos. His meddling has decreased over the years, and as far as we know, he's letting Showalter and GM Andy MacPhail run the team. That just makes the lack of progress even sadder, and the situation more hopeless.
Chicago CubsCurrent Record: 42-60
Last Winning Record: 2009
Last Playoff Appearance: 2008
Last Place Finishes Since 2000: 2
The Cubs have more playoff appearances than last place finishes this decade. They clearly have not been as outright putrid as the other four teams on this list. Of course, that's not why they're here. The Cubs are here because it's been 103 years and counting since their last World Series victory, and it looks like it's going to be a few years before they get another chance. The current team is mediocre, and the farm system is OK, but not great. However, the Cubs can rebuild much more quickly than the other 4 teams, thanks to having little financial constraints and a weak division to contend in. While it's certainly possible, it's unlikely the Cubs are going to fail to contend for decades at at time.
ConclusionSo, who is the most hopeless team in baseball, the one most deserving of the Pirates' former label of Biggest Laughingstock? While a case can be made for all five of these teams, I feel I must go homer in a perverse way and pick the Orioles. The combination of inheriting the consecutive losing seasons mark, the continuing presence of Angelos, trying to compete in the AL East, and seeing *another* set of prospects stall in the majors makes for one hopeless situation. There have been plenty of embarrassing moments during the vortex of suck as well (the 30-3 game, the recent Ortiz/Gregg bruhaha, every time Yankees and Red Sox fans invade Camden). In the end, it adds up to the Baltimore Orioles being the new Laughingstock of Baseball.