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1. The 1997 Florida Marlins
This is the standard against which all future first-to-worsts will be measured and of which all will fall short. To go from a parade to a 54-108 season, there can't be any invocation of the Plexiglas principle or bad luck or closing windows. It has to be, and it was, a controlled demolition.

Charles Johnson, Jeff Conine, Bobby Bonilla: gone, gone, gone at some point that offseason or early in 1998 when the team got off to starts of 1-11 and 17-44. Kevin Brown and Al Leiter, they were long gone by that point, too. An outfield of Moises Alou, Devon White, and Gary Sheffield became an outfield where Cliff Floyd was joined by Todd Dunwoody and the eternal Mark Kotsay. Young guys got their chances in bulk and with no greater shamelessness than in the pitching rotation that was by far the league's worst.

The 1998 Marlins blew away a record that year, giving 135 starts to pitchers who had yet to see their 24th birthdays. Naturally, they embarrassed themselves. Livan Hernandez was one of them, and he was okay, with a 4.72 ERA in 234 1/3 innings. Ryan Dempster somehow got a shot at age 21 and couldn't keep his ERA under 7.00, while Andy Larkin's 9.64 ERA in 14 starts and three relief outings was the third-highest ever for somebody with that many starts.

The 135 games started by the 23-and-under set was 15 more than any other National League team had in the Play Index era, and no team from either league has come within 30 games since.

The direct effect of the 1998 team on the 2003 World Series champions can be a little overstated. Sure guys got chances, but there were very few holdovers from the dreadful 1998 team when 2003 brought another parade. It was more about the organizational reset that allowed for multiple generations of young players to have a clear pathway.

Oh, and the American League record holder for 23-and-under starts was the 1967 Athletics with 125. They won the World Series five years later too. —Zachary Levine

2. The 2012 San Francisco Giants
Unlike the 1998 Marlins, the 2013 Giants closely resemble the squad that brought home San Francisco's second championship in three years. In fact, general manager Brian Sabean focused his offseason on keeping the band together. Angel Pagan signed a four-year, $40 million deal to stay with the Giants. Marco Scutaro came back on a three-year, $20 million hitch. Hunter Pence, briefly the subject of non-tender rumors, was retained through his final year of arbitration. And every member of the starting rotation was under contract through at least 2014.

In hindsight, a few fresh faces might have served the Giants well. Barry Zito, whose surprising postseason success was critical to the Giants' run at the pennant, is still winless on the road this season. Matt Cain, a perennially reliable rotation stalwart, also has faltered. Ryan Vogelsong went down with a broken hand, throwing a rotation that was remarkably stable in 2012 into turmoil. And, over the past couple of months, multiple members of Bruce Bochy's lineup fell into a synchronized slump.

Those searching for the turning point in the Giants' 2013 campaign, the moment at which the train began to come off the rails, might rewind to a moment that, at the time, thrilled the fans in attendance at AT&T Park. On May 25, with the Rockies in town and the Giants trailing, 5-4, in the bottom of the 10th, Angel Pagan clubbed a ball deep into the right-center field gap and sprinted around the bases for an inside-the-park, walk-off home run. Unfortunately, while the Giants won that battle, it might have cost them the war.

Pagan suffered a hamstring strain on the play, and his attempt to rest the injury was snapped during his rehab assignment, when he aggravated it running to first and crumbled to the ground. He went under the knife in late June and will not return to the field until 2014. The Giants improved to 27-22 with that walk-off victory, and they won again without Pagan the next day, moving to 28-22, good for a share of first place.

They have not stood atop the National League West since that day, going 19-37 over their last 56 games. That's a .339 winning percentage, for those of you scoring at home, worse than the Astros' .340 mark for the year, and a 55-win pace over a full season. To reiterate: if the Giants played this poorly over 162 games, they would win 55 and lose 107. The injury to Pagan, a 5.2 WARP contributor in 2012, could not have made all the difference. But the last two months would have you believe that it sent the defending champions from the top of the baseball world to the bottom. —Daniel Rathman

3. The 1914 Philadelphia Athletics
History has taken a nuanced view of Cornelius McGillicuddy, commonly known as Connie Mack. In addition to a number of records for longevity in the baseball business, Mack was known as a shrewd businessman. He famously said, “It is more profitable for me to have a team that is in contention for most of the season, but finishes about fourth. A team like that will draw well enough during the first part of the season to show a profit for the year and you don't have to give the players raises when they don’t win.”

Part of this cynical view can be explained by the fact that Mack had no source of income besides baseball. Despite winning World Series in 1910, 1911, and 1913, and a pennant in 1914, the Tall Tactician had fallen into debt. The newly formed Federal League began luring MLB stars with higher pay that offseason, which put huge pressure on Mack to meet the market for his stars. But Mack, rather than increase their salaries, let future Hall-of-Famers Chief Bender, Eddie Plank, Home Run Baker, and Eddie Collins walk away. (Bender spent 1915 with the Baltimore Terrapins, Plank with the St. Louis Terriers, Collins with the AL’s White Sox, and Baker sat out the entire season because of the contract dispute!) Mack replaced Collins with a 40-year-old Napoleon Lajoie, who would soon retire.

The 1915 A’s won just 43 games a year after winning 99. The 1916 campaign only got worse, with 37 wins and 116 losses. To this day, it is the most precipitous decline in history of a pennant powerhouse. —Dan Rozenson

4. The 1992-93 Toronto Blue Jays
Since 1976, only two franchises have won back-to-back World Series. It isn’t hard to recall that the Yankees were one of them, partly because they’re the Yankees and partly because they did it twice (’77-’78, and then three-peating from 1998-2000). Less celebrated are their division mates, the Toronto Blue Jays, who won the Series in 1992 and 1993—the latter year saw three of their players finish 1-2-3 in the batting title race, and Joe Carter’s electrifying, Series-ending, walk-off homer off of Philadelphia’s Mitch Williams in Game Six. That Series also featured the Jays’ extraordinary, record-setting, 15-14 comeback win in Game Four, which completely changed the direction of the series.

It might be harder to remember the Jays because they’ve placed better than third in the AL East only once in the last 20 years, a distant second-place finish in 2006. It’s probably a little unfair to judge the 1994 team because that was the strike year, but the 1995 team was a 56-88 disaster. Since then, they’ve been not so much awful as middling and colorless despite having had any number of excellent players over the years. In the extended, two-decade view, this has been one of the most disappointing franchises in baseball. This past winter, the Jays noisily gathered many shiny nest pieces, adding R.A. Dickey, Melky Cabrera, and about half the Marlins, and it was tempting to get on the Toronto-is-back bandwagon. Instead, the team has been plagued by injuries, regression, bad vibes, bad luck, and close-game allergies (they have baseball’s worst record in one-run decisions). They’re in last place in the AL East, a blazing 11-game June winning streak notwithstanding, and they already look rudderless again, doomed to more mediocrity. —Adam Sobsey

5. The 1933 Washington Senators
In 1933, the Senators won 99 games. A year later, they lost 86 games. There are various reasons for the downfall, including some symbolic—the cash-driven trade of Goose Goslin, Joe Kuhel breaking his ankle midseason, and so on. None stick out more than the downturn in starting pitching performance. The Senators started four pitchers 20-plus times in '33: Earl Whitehill, General Crowder, Lefty Stewart, and Monte Weaver. As a group those four started 124 games, threw 952 1/3 innings, and compiled a 4.02 run average. A year later the same quartet started 97 games, threw 692 innings, and averaged 5.44 runs against; they allowed almost the same amount of runs as they had the year before, despite throwing 260 fewer innings. The Senators found out the hard way that it's tough to win without decent starting pitching. —R.J. Anderson

6. The 1991 Minnesota Twins
Okay, they didn't completely turn into goo after winning the '91 World Series. They went 90-72 the following year, second behind the A's in the AL West. But the next eight seasons they became fish food for the rest of the American League. There are usually two good signs you have fallen off:

  1. A baseball movie is made about you struggling
  2. Bud Selig wants to contract you

After '92, they suffered eight straight losing seasons (their best showing was .469 in the 1994 abrupt-o-season). Chuck Knoblauch came into his own, but Kent Hrbek and Kirby Puckett didn't have much time left. John Smiley left for free agency, and their pitching rotation turned to an indoor cavalcade of sadness. The team's ERA+ from '91 to '95 went as follows: 116, 109, 92, 86, 84. Once their pitching became league average through the help of Brad Radke, suddenly the offense fell apart. Eventually everybody got frustrated and built an outdoor stadium. —Matt Sussman

7. The 1998 San Diego Padres
The 1998 season captured the nation's attention, and while most of the audience was tuned in to the McGwire and Sosa show, out in San Diego the Padres were marching toward their third playoff appearance in the 30-year history of the franchise. The '98 Padres had it all: a bona fide ace in Kevin Brown, whose 2.38 ERA in 257 innings netted a third-place finish in the Cy Young voting; a Hall of Fame hitter and face of the franchise in Tony Gwynn, whose isolated power of .180 was the highest of his career; a middle-order masher in Greg Vaughn, whose 50 homers broke the previously-established Padre standard by 10; and a shutdown closer in the form of Trevor Hoffman, whose 53 saves temporarily tied him for the second-highest total in baseball history. The team enjoyed another strong offensive campaign from Ken Caminiti, while right-hander Andy Ashby had the best season of his career, netting a 3.34 ERA in more than 225 frames. The Pads disposed of the Astros and Braves in the playoffs, but San Diego was steamrolled in the '98 World Series by the Yankees in a four-game sweep.

The Padres roster was overturned in the off-season of 1998-99, and the ensuing fallout frustrated a fan base that had already witnessed a fire sale following the 1992 season. Brown, who had arrived the previous off-season via the Marlins' fire sale, turned his big year into a free-agent payday with a nine-digit contract to wear a Dodgers uniform. Vaughn was dealt to the Reds for Reggie Sanders (and change), while Caminiti and outfielder Steve Finley also departed via free agency. Newcomers Sanders and Phil Nevin filled in admirably, but they were the only starters outside of Gwynn to crack a 750 OPS (meanwhile Vaughn tallied another 45 bombs and 118 Ribs for Cincy), and the top-hitting trio of Pads averaged just 124 games between them in the '99 season. The 39-year-old Gwynn battled injuries which limited him to 111 games played, and though Ashby put up a solid follow-up campaign to his '98 breakout (3.83 ERA in 206 innings), he was the only San Diego starter to finish under the 4.00 mark. The Friars slipped to a 74-88 record, 24 games off of their '98 pace, kicking off a five-year run of fourth- and fifth-place finishes out West.

The '98 Pads caught lightning in a bottle, and the combination of regression and roster turnover conspired to send the '99 team below the depths of .500. It would have been cost-prohibitive to retain a roster with so many key players headed to free agency, and in retrospect, the club made the right decisions—Brown was a 34-year-old pitcher who received a seven-year, $105 million deal to play ball into his 40s; the 36-year-old Caminiti would play just 248 games over his final three years in the bigs; and Vaughn's career would nose-dive following the '99 season (while Sanders became a key cog in the trade that brought Bret Boone and Ryan Klesko to San Diego). The '98 squad was an aging team—not one of their regular starters in the lineup or the rotation was under the age of 27, and six of their eight regular position players were on the wrong side of 30—and management stuck to their guns amid this harsh reality, rather than spend lavishly in a veiled attempt to recapture the magic. —Doug Thorburn

8. The 1964 New York Yankees
Dynasties can be sustained for only so long before the cracks in the core begin to show. Aging stars stick around too long for sentimental or contractual reasons; front offices fail to replenish the team’s young talent, either out of complacency, a reluctance to trust unproven players, or an inability to strike gold again. Eventually enough rust accumulates that the team reaches the tipping point into non-contention.

The Yankees finished over .500 for 39 straight seasons from 1926-1964 not just because they were wealthy, but because they were smart, adept at scouting, and very vigilant about putting succession plans in place. When Lou Gehrig retired, there was Joe DiMaggio; when DiMaggio retired, there was Mickey Mantle. And it was the same with the organization’s complementary players, who unfailingly arose to shore up any area in which the roster seemed to be slipping. (It didn’t hurt that that for a while, the Kansas City Athletics functioned as a Yankees farm team.)

Powered by a bunch of names you know, the Yankees won five consecutive pennants from 1960-1964, but by ’65, those cornerstone players were mostly past their primes. Mantle, an old 33, declined from 6.9 WARP to 2.8. Roger Maris, at 30, fell from 4.3 to 1.0. Elston Howard, at 36, went from 6.1 to 0.3. Tony Kubek went from above average to injured and below replacement, then retired. There were young position players, but even the ones who had some staying power—Joe Pepitone, Horace Clarke, Roger Repoz—weren’t the equals of the ones who went before. (Bobby Murcer and Roy White got cups of coffee but weren’t ready for regular roles.) With the exception of Mel Stottlemyre, who had what would prove to be a career year in his first full season, and a still-effective Whitey Ford, the pitching staff struggled. Jim Bouton blew up, and failings in the field (the team’s defensive efficiency fell from second to 13th) made the pitching look even worse than it was.

Throw in some bad luck—the ’65 Yankees finished five games under their Pythagorean record; the ’66 team finished nine games under theirs, going 15-38 in one-run games—and a manager, Johnny Keane, who wasn’t well suited to the team (“It was like Billy Graham in charge of the Hell’s Angels,” Bouton said), and you had the makings of what for this franchise would be a prolonged dry spell. The Yankees wouldn’t make it back to October until 1976, by which point—with the exception of White—the roster had entirely turned over. —Ben Lindbergh

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As Mr. McGillicuddy's corresponding secretary, he has asked me to write to you today about a minor typographical error in your missive regarding his Baseball Club. Mr. McGillicuddy was the owner/operator/manager of the *Philadelphia* Athletics from 1901 through 1950, not this "Oakland" franchise that you refer to in your article. Please correct this inaccuracy with all due celerity.
Inaccuracy corrected.
Thought for sure the 2003 Angels would make this list. Apparently, they weren't quite pathetic enough.
'93 Phillies deserve an honorable mention, as they followed up their WS appearance with 7 losing seasons in a row.