First, some teams that could be considered but probably aren't. The Nationals are back below .500, but are getting closer and have big time talents coming in Bryce Harper and Stephen Strasburg. The Mets and Dodgers have certainly been embarrassing off-the-field, but both teams have recently been playoff teams. Finally, Moneyball haters would love to say the Athletics, but they've been more consistently mediocre than consistently bad.
Without further ado, the nominees...
Seattle MarinersCurrent Record: 43-59
Last Winning Season: 2009
Last Playoff Appearance: 2001
Last Place Finishes Since 2000: 5
The Mariners weren't the first team to come to mind, that is, until they went on a 16 game losing streak. The M's have two great pitchers in King Felix and Michael Pineda, but the big problem here is the offense. Last year they scored a putrid 3.17 runs per game, one of the worst offensive performs since the advent of the DH. This year the M's have improved...to 3.28 runs a game. The future doesn't look much better. Their current roster has exactly two guys with potential: Justin Smoak (who hasn't really shown it) and Dustin Ackley (who has, but it's still very early for him). Ichiro is clearly in decline and the Chone Figgins deal with a disaster. What's amazing is the M's haven't made the playoffs since their 116 win 2001. While they have two stud pitchers and Ackley, the farm system is thin, and there's definitely a concern this is just the start, continuation really, of a long, hard road.
Kansas City RoyalsCurrent Record: 43-59
Last Winning Season: 2003
Last Playoff Appearance: 1985
Last Place Finishes Since 2000: 7
Anyone that's read Joe Posnanski or Rany Jazayerli knows the embarrassing 25+ years of the Royals. This encapsulates the history well (in musical form!). That 2003 fluke season is actually the only above .500 for the Royals since 1993. Really, if this were solely based on past results, the Royals would win easily. However, the Royals have a trump card the other teams on this list don't have: a great farm system. Will all their great prospects pan out? Of course not. In fact, the left handed pitchers (Mike Montgomery, John Lamb, Danny Duffy) have struggled with injury and ineffectiveness. Two of the big-time hitters, Eric Hosmer and Mike Moustakas, are already up in the bigs, and there's more coming, including yet more pitching. Given that I'm thinking more future than present or past, the farm system keeps Kansas City from "winning" this battle for now, as the prospects give them some kind of hope. If they fail though, look out...
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.