The failure dynasties   

Updated: May 4, 2008, 8:48 PM ET

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It's really tough to build a winning dynasty in Major League Baseball, this much we know. Reeling off a streak of winning seasons is hard enough, never mind stringing together multiple World Series victories. So many teams came close to achieving immortal status only to fall short that we rolled out an entire series on failed dynasties.

Building a lasting loser, though? That's a lot easier. The Baltimore Orioles, Pittsburgh Pirates and Tampa Bay Rays are riding streaks of 10 or more losing seasons. Add in the Royals and Expos/Nationals, and those five teams have combined for more losing seasons than the Washington Generals. Forget failed dynasties. These are the failure dynasties.

Two teams made a strong case to be included in our feeble five. The Milwaukee Brewers haven't tasted the postseason since 1982, the second-longest playoff-less streak in the game. From 1994 to 2006, the team never finished above .500. The Brewers finished last or second-to-last seven times in those 13 seasons, including three straight years in the cellar from 2002 to 2004. But Milwaukee's now a team on the upswing, coming off 83 wins and a second-place finish, with a core of young talent that's expected to contend for a division title. The Brewers are exempt.

The Cincinnati Reds own the fifth-longest streak of losing seasons, with seven. Counting Ray Knight's one-game tenure, five managers handled the reins in those seven seasons, either in permanent or interim positions. That seven-year itch included a three-year stretch in which the Reds' arsonist pitchers were last in the National League in park-adjusted ERA. But Cincy misses the cut, partly because of optimism toward a team that suddenly looks like a contender, but mostly because Kansas City, despite a more recent winning season, has a more impressive track record of losing.

The Texas Rangers have just one winning season in the past eight years, finishing last in the AL West five times in that stretch. The Rangers can't blame a lack of resources for the streak, either, as they've signed a number of players to big, multiyear deals. But Texas doesn't quite make it either: The Rangers won 89 games just four years ago, with a stretch of three division titles in four years in the late '90s.

With those pretenders out of the way, here are the five teams riding the biggest losing streaks in baseball, their signature moments and their hopes for the future.

BALTIMORE ORIOLES
Length of streak: 10 straight losing seasons
Last winning season: 98-64, 1997
General managers: Pat Gillick (1998), Frank Wren (1999), Syd Thrift (2000-2002), Jim Beattie/Mike Flanagan (2003-05), Flanagan (2006-07), Andy MacPhail (2007-)

Five bad moves
1. Firing Davey Johnson. Yes, he has an ego, and there's a long list of owners and front-office people who've struggled to get along with him. But all he's ever done is win, in New York, in Cincinnati and, yes, in Baltimore. The year before Davey Johnson took over, the Orioles finished two games under .500. The next season, they won 88 games and the wild card, followed by a 98-win season and a division title. The O's cut him loose, and they haven't sniffed .500 since. But sure, Peter Angelos, you go right on losing games and watching your attendance dwindle. At least you showed everyone who's boss.

Albert Belle

Getty Images

Albert Belle … just one of many Baltimore free-agent signings that didn't pay off.

2. Signing Albert Belle to a five-year, $65 million contract. For all the Orioles' losing, no one could ever blame Angelos for being cheap, and this contract was Exhibit A of the owner's largesse. Belle had one of the best career peaks in baseball history, putting up gigantic numbers. But in giving him such a massive deal after the 1998 season, including a no-trade clause for the first three years, the O's were betting that Belle would stay healthy and hugely productive well into his mid-30s. Instead, Belle played just two more years before a degenerative hip injury forced him to retire.

3. Hiring Syd Thrift, Jim Beattie and Mike Flanagan as GMs. Thrift was years past his prime as a talent evaluator, while Beattie and Flanagan owned lackluster track records and did little to move the team forward during their tenure as co-GMs. Of course in Baltimore, a willingness to say yes to the big boss usually transcends a winning résumé.

4. Trading for Sammy Sosa. In the final, $17 million season of a ginormous contract, Sosa had a .221 batting average, a .295 on-base percentage and .376 slugging. He hit 14 homers and played just 102 games. The trade didn't cost the Orioles any impact prospects. But it was a classic example of the kind of short-sighted, money-wasting moves that have plagued this team for more than a decade.

5. Nearly everything else they did in 2005. The O's jumped out to an early division lead in 2005, holding first place for 62 days. By season's end they'd lost 60 of their final 92 games, squandered $17 million on Sosa and fired yet another manager. The coup de grace came from Rafael Palmeiro, who started the year by testifying in front of Congress that he'd never used steroids, cracked his 3,000th hit on July 15, then got suspended 15 days later for testing positive for steroids.

Lowest moment: Facing the Texas Rangers at Camden Yards on Aug. 22 of last year, the Orioles gave up 30 runs, setting a modern-era record for a single game. The O's actually led 3-0 early in the game before allowing 30 straight runs in the 30-3 loss.

Favorite whipping boys: Peter Angelos. Every player, manager, GM and hot dog vendor who failed to do the job in the past 10 years is an extension of Angelos' reign of error.

Notable quotable: "This is something freaky. You won't see anything like this again for a long, long time." --Rangers outfielder Marlon Byrd, after hitting one of Texas' two grand slams in the Rangers' 30-3 annihilation.

Hope for the future? The 15-13 start is nice, but the Orioles probably won't see a winning season for a while. Nick Markakis and Adam Jones are great building blocks in the outfield, Luke Scott is an above-average player as the third outfielder, Brian Roberts and George Sherrill should fetch some interesting loot in a trade, and Matt Wieters is a potential franchise player a year away from taking over at catcher. After that, the closet is nearly bare, with a severe lack of pitching the biggest problem.

ETA for next winning season: 2012.

KANSAS CITY ROYALS
Length of streak: 12 out of 13 losing seasons, no playoff berths in 22 years
Last winning season: 83-79, 2003
Last winning season before that: 64-51, 1994
General managers: Herk Robinson (1995-2000), Allard Baird (2001-06), Dayton Moore (2006-)

Five bad moves
1. Trading Johnny Damon and Mark Ellis for Roberto Hernandez, Angel Berroa and A.J. Hinch. Damon's still starting for a championship-caliber team seven years later. Ellis was an afterthought in the trade, but he's become one of the best all-around second basemen in the game. Meanwhile, Hernandez is out of baseball and Berroa may as well be. On the plus side, Hinch is doing a great job with the first-place Diamondbacks -- as director of player development.

2. Trading Jermaine Dye for Neifi Perez. There are a hundred ways to measure Jermaine Dye versus Neifi Perez in the 6Ż years since this deal was made. Sometimes keeping it simple works best:

Homers since trade:
Dye 169
Perez 21

3. The Colt Griffin/Roscoe Crosby draft. The Royals couldn't have been more thrilled when they made these two high school phenoms their top two picks in the 2001 amateur draft. Griffin went from an unknown first baseman to darling of the scouting world within two months, wooing prospect hounds with a fastball that touched 100 mph and a storybook name. Crosby was a lefty-swinging outfielder considered by some to be the best athlete in that year's draft. Too bad the Royals ignored the negatives. Griffin was a great thrower but not a pitcher -- injuries and ineffectiveness chased him out of baseball. Meanwhile, the Royals got Crosby in the second round only because other teams feared he'd opt for a career in football -- which is exactly what he did.

Squandering high draft picks, something each of these teams has had in spades for years because of their lousy records, is a common theme here.

4. Passing on a chance to move to the National League. In 1997, with MLB set to usher in expansion teams from Arizona and Tampa Bay, the Royals were offered a chance to switch to the National League as part of a realignment plan. Here was a chance for Kansas City to forge an intrastate rivalry with St. Louis, likely driving greater interest and attendance for the team, while escaping the American League, ruled at the time by the dynastic Yankees (and later populated by other well-heeled powers like the Red Sox and Angels). Kansas City ownership, a faceless, inert group four years after the death of long-time owner Ewing Kauffman and three years before David Glass took the reins, decided to … do nothing.

5. Hiring Tony Muser, then waiting so long to fire Tony Muser. In baseball, as in life, you can't make chicken salad out of chicken poop. But while the Royals may have lacked premium talent throughout most of his tenure, Muser only made matters worse in his five years as manager, compiling a 317-431 record in the process. A slick-fielding, banjo-hitting first baseman in his playing days, Muser gave far too much playing time to similarly punchless first basemen on his teams. After watching the Royals saddle Jose Rosado with more than 200 innings pitched at the minor league and major league levels at age 21, Muser sent him back out for 203 more at age 22; Rosado was out of baseball three years later. More than just a butcher at building a lineup or making in-game decisions, though, Muser just wasn't cut out to be a major league manager. As long-suffering Royals fan Rob Neyer put it: "You had to watch Muser regularly to really appreciate him."

Lowest moment: Following the first 100-loss season in franchise history in 2002, new manager Tony Pena improbably guided the team to an 83-win season in '03, dramatically raising expectations. The Royals responded with a 7-14 April in 2004 on their way to 104 losses.

Favorite whipping boys: Tony Muser, Buddy Bell, Allard Baird, David Glass, Angel Berroa, Neifi Perez, Lima Time!

Notable quotable: "We got the best high school arm in the country, and we got probably the best athlete in the draft. If somebody would have told me before the draft we were going to get Mr. Griffin and Mr. Crosby, I would have said 'You're nuts.'" --GM Allard Baird

Hope for the future? Plenty, actually. A top three of Zack Greinke, Gil Meche and Brian Bannister in the rotation suddenly looks really promising. Billy Butler hits like Ichiro, even if it also looks he ate Ichiro. Alex Gordon's a future star. Joakim Soria is a young, cheap, lights-out closer and the key man in a very good bullpen.

ETA for next winning season: 2009.

PITTSBURGH PIRATES
Length of streak: 15 straight losing seasons
Last winning season: 96-66, 1992
General managers: Cam Bonifay (1993-2001), Dave Littlefield (2001-07), Neal Huntington (2008-)

Five bad moves
1. Keeping Andy Van Slyke instead of Barry Bonds. Van Slyke was wildly popular with the fans, he wasn't half the diva that Bonds was, and his asking price was much lower. But when Pittsburgh chose to keep Van Slyke after the team's stretch of three straight division titles (1990-1992), it ranked as one of the worst decisions in baseball history. The Pirates haven't had a winning season since.

2. Sticking with Cam Bonifay for too long as GM. Bonifay took the reins in 1993, inheriting a suddenly talent-starved team that had just lost the future all-time home run king. But in his eight years as general manager, Bonifay got stuck in the mud and never dug himself out. Failing to rebuild the farm system, the Pirates tried to compensate by dishing out big contracts to mediocre players (Mike Benjamin! Pat Meares!! Kevin Young!!!) and gigantic contracts to players a step above mediocrity. The six-year, $60 million contract he gave Jason Kendall remains one of the worst deals of an entire generation.

Derek Bell

Tom Pigeon /Getty Images

Derek Bell gave Pirates fans only one of the great nicknames in baseball history.

3. Sticking with Dave Littlefield for too long as GM. His trade record was a mixed bag, with some successful moves (acquiring Jason Bay from the Padres, albeit only after San Diego refused to give up Xavier Nady) balanced by a few stinkers (tossing future All-Star pitcher Chris Young overboard for Matt Herges). His greatest downfall was his woeful drafting and development record: The team exited the Littlefield era with a farm system in no better shape than it had been 6½ years earlier, despite owning top-10 draft picks every year.

4. Drafting Bryan Bullington No. 1 overall in 2002. Littlefield's draft record was best exemplified by taking Bullington, a college pitcher projected more as a safe, back-of-the-rotation starter than an ace, over the consensus top talent, B.J. Upton (who went No. 2 to the Devil Rays). Other first-rounders Littlefield passed up that year: Prince Fielder, Jeff Francis, Jeremy Hermida, Scott Kazmir, Nick Swisher, Cole Hamels, James Loney, Jeff Francoeur and Matt Cain.

5. Selling the franchise to Kevin McClatchy. In a sense, it's hard to call the McClatchy Era a bad move. A team can pick its players, coaches, manager, GM, scouts and other personnel. But it can't pick the people who run the whole show, and therein lies the problem for many teams, especially the Pirates. The head of a publishing empire, McClatchy headed a group of owners who did everything on the cheap from 1996 to 2007, even after a beautiful, new, taxpayer-funded stadium landed in their laps. Everything from choosing signability over talent in the draft to sticking with the team's ineffectual GMs too long can be blamed on hapless ownership.

Lowest moment: Facing the Cubs on the second-to-last day of the 2001 season, the Pirates got crushed by a score of 13-2, their 100th loss of the season. It was the first time the Bucs dropped 100 games in 16 years.

Favorite whipping boys: Derek Bell, Kevin Young, Pat Meares, Mike Benjamin, Lloyd McClendon, Jim Tracy, Cam Bonifay, Dave Littlefield, Kevin McClatchy.

Notable quotable: "Nobody told me I was in competition. If there is competition, somebody better let me know. If there is competition, they better eliminate me out of the race and go ahead and do what they're going to do with me. I ain't never hit in spring training, and I never will. If it ain't settled with me out there, then they can trade me. I ain't going out there to hurt myself in spring training battling for a job. If it is [a competition], then I'm going into 'Operation Shutdown.'" --Pirates outfielder Derek Bell's reaction to competing for a starting job with the Pirates in spring training 2002, after hitting .173 the year before. True to his word, Operation Shutdown never played another game in the big leagues.

Hope for the future? Ian Snell's a keeper in the rotation. Nate McLouth may be in the early stages of a breakout season. Ryan Doumit should be a solid run producer at catcher. Andrew McCutchen is a five-tool prospect in center field. But the biggest hope resides in the front office, where new GM Neal Huntington has surrounded himself with a top-rate staff of baseball minds who should help the Bucs get back on the winning track. It won't happen right away, though -- the Pirates have a terrible farm system for a team that has had so many high draft picks.

ETA for next winning season: 2010.

TAMPA BAY RAYS
Length of streak: 10 years of existence, 10 losing seasons
General managers: Chuck LaMar (1998-2005), Andrew Friedman (2006-)

Five bad moves
1. Trading Bobby Abreu to the Phillies for Kevin Stocker. Management showed a keen eye for talent in picking a future star in Abreu during the 1997 expansion draft. The decision the same day to trade Abreu for Stocker, a light-hitting shortstop who lasted just three more years in the majors, didn't go quite so well. This is probably one of the 25 worst trades in major league history.

Greg Vaughn

Al Bello/Getty Images

Greg Vaughn's final season in Tampa ended with a .163 average in 69 games.

2. Paying big bucks for Vinny Castilla and Greg Vaughn. Rather than wait for their farm system to bear fruit, the Rays added Castilla and Vaughn to a veteran core that already included Fred McGriff and Jose Canseco, hoping to replicate the success the Blake Street Bombers had in Colorado a few years earlier. One of those Bombers, Castilla, proved to be a lousy hitter at normal altitude, giving the Rays little return for their $13.5 million over two years. After hitting 95 homers the two previous seasons, Vaughn also slowed down considerably in Tampa, while costing the team more than $24 million over three years.

3. Handing the keys to Chuck LaMar. Like Thrift in Baltimore, LaMar was respected as a shrewd talent evaluator for years (with the Braves) but was over his head as a general manager. Some of the players drafted and developed during his tenure, including Carl Crawford and B.J. Upton, look like potential stars. But there also were far too many misses for a team that constantly drafted in the top 5. That their expansion cousins in Arizona won three division titles and a World Series in their first five years of existence only makes things look worse.

4. Trading Randy Winn to the Mariners for the right to negotiate with future manager Lou Piniella. Sweet Lou had garnered his share of success as a manager, and pursuing the Tampa native for the job made some sense. Still, giving up an above-average major league player for the right to throw millions of dollars at a manager was a move that typifies the team's existence under LaMar. Piniella did what he could, but the team still lost 285 games in his three years in the dugout.

5. Signing a 30-year lease for Tropicana Field. The worst real estate deal since the sale of Manhattan for 24 bucks. The team has been trying to negotiate out of it and get a new stadium since the moment pen hit paper.

Lowest moment: So many to choose from … maybe the time original owner Vince Naimoli allowed a local furniture store to set up a showroom at Tropicana Field, complete with dangling price tags.

Favorite whipping boys: Vince Naimoli, Chuck LaMar, Greg Vaughn, Vinny Castilla, Jose Canseco, Ben Grieve, many pitchers too numerous to name.

Notable quotable: "I believe it's a good idea. And the reason I believe it's a good idea is that there are some markets where I just don't think baseball works." --Naimoli, commenting on contraction in 2002.

Hope for the future? More than almost any other team in baseball. Led by new owner Stuart Sternberg and a savvy collection of front-office decision makers, the Rays have gone from being a butt of jokes to a potential powerhouse. The Rays own the best collection of young talent in the game: Crawford, Upton, Carlos Pe˝a, Evan Longoria, Scott Kazmir, James Shields and Matt Garza plus pitching prospects David Price, Wade Davis and Jacob McGee. Tampa still hasn't had a winning season. But once the first one happens, the Rays might not go back to losing for a long time.

ETA for next winning season: 2008.

WASHINGTON NATIONALS/MONTREAL EXPOS
Length of streak: The longest playoff drought of any club in the four major pro team sports, 26 years
Last winning season: 83-79, 2003
General managers: Kevin Malone (1995), Jim Beattie (1996-2001), Omar Minaya (2002-2004), Jim Bowden (2005-)

Five bad moves
1. The post-strike fire sale. Greed and stubbornness by the owners and players wiped out the end of the 1994 season, the playoffs and the best-in-baseball Expos' chances for a World Series run. Rather than push forward with the best young core of talent in the game, ownership ordered GM Kevin Malone to dump as many star players as possible in a week's time. The end result was a disastrous series of moves that ripped apart a loaded team while also failing to replenish the farm system. Marquis Grissom, Ken Hill and John Wetteland were jettisoned for pennies on the dollar. The Expos let hugely popular Canadian star Larry Walker walk without even offering him arbitration, ensuring that the team received nothing in return.

Pedro Martinez

David Greene/Getty Images

Um, yeah, trading Pedro wasn't such a good idea.

2. Trading Pedro Martinez for Carl Pavano and Tony Armas Jr. Of all the cheapskate moves engineered by Montreal's owners, the trade of Martinez to the Red Sox ripped out the hearts of Expos fans. Just 26 years old and coming off his first Cy Young Award, Pedro still had the best years of his Hall of Fame career in front of him. Instead, the team settled for Pavano and Armas, two talented young pitchers whose careers were derailed by constant injuries.

3. Jeffrey Loria engineering a blackout. Early in the Expos' history, owner Charles Bronfman relinquished broadcast rights in southern Ontario to the fledgling Toronto Blue Jays, as a favor to Canada's newest team. The move would prove disastrous, giving the Jays the platform they'd need to become a large-market power while forever condemning the Expos to small-market purgatory.

Heading into the 2000 season, owner Jeffrey Loria dealt a similarly cruel blow to the franchise's fortunes, though with far less honorable intentions. Loria supposedly shopped the team's TV and English radio rights around that year, but found no takers at his asking price. Rather than chalk up broadcasting rights as marketing costs, the Expos went dark in every medium except French radio that season, dealing a devastating blow to the team's already teetering fortunes. Given how conveniently Loria managed to bail on the Expos and reap huge rewards from the franchise sale, then extort the taxpayers of Florida into a lucrative taxpayer-funded stadium deal years later, it's easy to speculate that Loria sabotaged the Expos' final days in Montreal, with tacit approval from his accomplice Bud Selig.

4. Trading Grady Sizemore, Brandon Phillips and Cliff Lee for Bartolo Colon. Before the 2002 season, the Expos were identified as a prime candidate for franchise contraction. When the team surprisingly stayed in contention for a few months, GM Omar Minaya made a what-the-heck trade, acquiring Colon from the Indians. The go-for-it deal was a rare, pleasant surprise for Montreal fans, used to seeing their team trade away established stars. But the bounty sent to Cleveland in return was considered a king's ransom at the time, a short-sighted trade made under duress, even for an ace like Colon. Six years later, Nationals fans can only fantasize about Sizemore and Phillips playing alongside Ryan Zimmerman, with Lee fronting the starting rotation.

5. Failing to re-sign Vladimir Guerrero. Another future Hall of Famer, another unceremonious departure. The Expos supposedly offered Vlad a contract extension before he hit free agency, though the offer came in well below market value. The Angels snapped him up, getting a new franchise player in the process. OK, Nats fans, now imagine an outfield of Sizemore, Vlad and Lastings Milledge, with an infield anchored by Zimmerman and Phillips.

Lowest moment: Maybe you can trace the franchise's downfall to 1991, when a 55-ton concrete beam crumbled off the fašade of Olympic Stadium and crashed onto a walkway. The Expos played their last 13 home games on the road, failed to reach .500 for the first time in five years, failed to reach 1 million in attendance for the first time since the Big O opened and added another chapter to their ill-fated history.

Favorite whipping boys: Bud Selig, Claude Brochu, Jeffrey Loria, Tom Runnells, Hideki Irabu, Brad Fullmer.

Notable quotable: "This was a team that had to be moved. We knew it had to relocate. Baseball didn't want to own it anymore. This was a team owned by baseball that we were anxious to get rid of." --Commissioner Bud Selig on the Expos' move to Washington after the 2004 season.

Hope for the future? Zimmerman and Milledge are 23-year-old twin building blocks for the offense, and top prospect Chris Marrero provides another potential impact bat down the road. But the pitching is thin both at the major league level and in the high minors. There's enough midlevel talent for the team to be respectable right now, but not nearly enough for the team to be really good for several years.

ETA for next winning season: 2012.


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