The departures of Bobby Bonilla (left) and Barry Bonds helped set Pittsburgh on its way to two decades of futility. (Al Tielemans/SI)

The Pirates won their 81st game Tuesday night, breaking a streak of 20 consecutive losing seasons that began in 1993. With their next win, they will clinch their first winning season since 1992. To give you an idea of how long ago that was, when the Pirates last secured a record above .500 it was Sept. 12, 1992, George H.W. Bush was president. Bill Clinton was still the Governor of Arkansas. Brewers owner Bud Selig was in his third day on the job as acting commissioner of Baseball. Kate Upton was three months old, and Bryce Harper hadn't even been born. Harper's birthday -- Oct. 16, 1992 -- came two days after Braves pinch-hitter Francisco Cabrera drove home ex-Pirate Sid Bream with the winning run in the bottom of the ninth inning of Game 7 of the 1992 National League Championship Series to eliminate Pittsburgh from the its most recent postseason appearance.

Two decades of losing followed in the Steel City. In recognition of the Pirates finally snapping that streak, here, in chronological order, is a look back at the 20 worst moments in the team's 20 years of losing, all of which can now finally be confined to history as the 2013 Pirates head back toward the postseason.

1. Barry Bonds and Doug Drabek depart as free agents, December 1992

Before the Pirates’ losing was notable for its duration, it was notable for its suddenness. Under manager Jim Leyland, Pittsburgh had won the National League East three straight years from 1990 to 1992, but their inability to offer competitive contracts to their free agent stars led to the departures of rightfielder Bobby Bonilla after the 1991 season, and Bonds and Drabek after the 1992 campaign. Bonilla (Mets, $39 million for five years) and Bonds (Giants, $43.75 million for six years) both signed record-breaking contracts. Drabek signed with the Astros for $19.5 million over four years, a seemingly modest deal in retrospect, but one with an average annual salary that would have set a record just two years earlier.

Pittsburgh survived the departure of Bonilla, who had finished in the top three in the NL Most Valuable Player voting in both 1990 and 1991, but were unable to endure the additional losses Drabek, the staff ace and 1990 NL Cy Young award winner, and Bonds, the 1990 and 1992 NL MVP and arguably the best player in the game. Bonds and Drabek were worth a combined 13.5 wins above replacement in 1992 (per Baseball-Reference.com’s numbers, hereafter bWAR), and without them the team fell from 96 wins in 1992 to 75 in ’93.

2. Seven double-plays, June 16, 1994

The Pirates were on pace for another 75-win season in 1994 before the strike put them out of their misery, but the work stoppage didn’t come soon enough to prevent them from displaying the sort of futility that would become their hallmark. On June 16, they hit into seven double plays against the Cardinals, one shy of the record set, coincidentally, by St. Louis against Pittsburgh in 1959. To put that in perspective, the Pirates used up 14 of their 27 outs, one more than half, on seven swings of the bat. Remarkably, they won the game 7-5 in 10 innings. The Pirates grounded into DPs in the first, third, fourth, fifth, sixth and ninth innings, and cut short their 10th-inning rally when 38-year-old catcher Lance Parrish was thrown out at third base by the rifle-armed Mark Whitten on a bases-loaded sacrifice fly to rightfield. Only one other team, the 1982 Reds, has ever been the victim of seven double plays in a game.

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3. Tim Wakefield released, April 20, 1995

It didn’t seem like a mistake at the time. The Pirates had drafted Wakefield as a first-baseman in 1988, fostered his conversion to pitching and the development of his knuckleball and enjoyed the fruits of their investment when he went 10-1 in 15 starts between the regular and postseasons in 1992. With Drabek gone, Wakefield was the team's Opening Day starter in 1993, but he lost his rotation spot by mid-June and spent most of July and August in the minors. He then had offseason elbow surgery and didn't make the big league club in spring training, spending all of his age-27 season in the minors, where he went 5-15 with a 5.84 ERA for Triple-A Buffalo. After he failed to make the team again in 1995, the Pirates gave him his release less than a week before that season’s belated Opening Day.

Just six days later, the Red Sox signed Wakefield and he proceeded to go 16-8 with a 2.95 ERA for AL East champion Boston that season. He would pitch 17 seasons for the Red Sox, helping them to two World Series titles and winning 186 games, third in franchise history behind only Cy Young and Roger Clemens.

AP

4. Attendance drops below one million, 1995

By 1995, the Pirates had seen Bonilla, Bonds, Drabek and aging fan favorite Andy Van Slyke leave as free agents, and after two losing seasons and an eight-month work stoppage, the Pirates team that returned in ’95 was the worst to wear black and gold since 1986. To be fair, had there been 162 games in the 1995 season, rather than the strike-shortened 144, the Pirates would have cracked one million in attendance, but even with that shortened season, every other team in baseball that season reached that benchmark. In fact, even in the still-shorter 1994 season, every team in baseball out-paced Pittsburgh, which drew only 905,517 to Three Rivers Stadium. The average attendance for Pirates home games in 1995 was 12,577, the lowest mark since that of the 1990 Braves. Since '95 only eight teams -- the 1998 to 2002 and 2004 Expos, 2000 Twins and 2002 Marlins -- have failed to draw one million.

5. The worst month: September 1998

The Pirates went 5-22 in September 1998, their worst single-month performance of their 20 consecutive losing season. Before that skid, which actually began on Aug. 28, the Pittsburgh was just four games below .500 and 8 1/2 games out of the NL wild-card race in third place in the NL Central. Over their final 30 games, however, the Bucs would go 5-25, a mere .167 winning percentage, while scoring just 80 runs and allowing 162, just over twice that many. They finished dead last in the Central with a 69-93 record, 21 games behind the wild-card winning Cubs. Pittsburgh's .423 winning percentage was, to that point, the second-worst of their streak of losing seasons, better than only its .403 mark in 1995.

6. Jon Lieber traded, Dec. 14, 1998

One of Cam Bonifay’s first moves as Pirates general manager after taking over for an ailing Ted Simmons in mid-1993 was to steal minor league righty Jon Lieber from the Royals in a deadline deal for reliever Stan Belinda. After some fits and starts, Lieber finally established himself as a rotation stalwart in 1997 and ’98, the latter his age-28 season. In doing so, he got expensive, pushing his salary into seven digits via arbitration prior to the 1998 campaign.

That was one reason that Bonifay traded Lieber after that season to the Cubs for outfielder Brant Brown, who had hit .291/.248/.501 in 380 plate appearances in '98. Brown was to be the Pirates’ new centerfielder, but he was just a year younger than Lieber and far less established. Brown fell below replacement level in ’99, was out of Pittsburgh in ’00, out of the majors in ’01 and out of baseball in ’02. Lieber, meanwhile, won another 93 games in the major leagues including a 20-6 season for the Cubs in 2001.

7. The Pat Meares extension, April 30, 1999

The Lieber trade looked even worse in light of how Bonifay spent the money he saved, as well as the additional money he was allowed to spend when owner Kevin McClatchey upped the team’s payroll that winter. In March, Bonifay signed first-baseman Kevin Young to a four-year, $24 million extension, the largest contract ever given out by the Pirates to that point. Then there was the Pat Meares contract.

A slick-fielding shortstop, Meares hit .265/.301/.381 over six seasons with the Twins before being non-tendered in December 1998. The only team to offer him a starting job that winter was the Pirates, who signed the 30-year-old Meares to a one-year, $1.5 million contract in February 1999. No big deal thus far, but at the end of spring training, Meares suffered an injury to his left hand, and on April 30, just one week after he had been activated from the disabled list, Bonifay gave Meares a four-year extension worth $15 million, the third-richest deal ever handed out by the Bucs, and called him, “the type of player who can help make us a championship team.”

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Twelve days after signing his extension, Meares landed back on the DL and had surgery to repair a fractured bone and torn tendons in his left hand. He played just four more games in 1999. Meares largely repeated his Twins production in 2000, the first year of his extension, but hit the DL again in late June 2001 and was a part-time player after his return. Meares hit a, ahem, mere .211/.255/.304 in 2001. After a poor spring in 2002, the Pirates put him on the disabled list and attempted to recover a portion of his salary via insurance. Meares disagreed with the team’s assessment of his health and filed a grievance against the franchise that July arguing that he was fit to play. Meares ultimately dropped his grievance and spent the final two years of his extension, and his career, on the disabled list. In parts of three seasons as a Pirate, for which he was paid $16.5 million, Meares hit .238/.294/.352 with a 64 OPS+ and was worth 1.2 wins less than a replacement-level player per bWAR. The Pirates ultimately recovered roughly $5.25 million of Meares’ salary via insurance.

8. Jason Kendall breaks his ankle, July 4, 1999

One of the few bright spots for the Pirates in the late ‘90s, catcher Jason Kendall finished third in the Rookie of the Year voting in 1996, was an All-Star in two of his first three seasons and was Pittsburgh's best position player in 1997 and 1998. He was back at it in 1999, hitting .332/.428/.511 when, with one out in the bottom of the fifth inning of a game the Pirates were losing 3-0 to the Brewers at Three Rivers Stadium on Independence Day, Kendall attempted to bunt for a hit. He was out, and when he crossed first base, his right foot hit the bag at a bad angle, causing him to roll over his ankle, tearing all of the ligaments in the joint. It was a gruesome, season-ending injury that robbed Kendall, who had stolen 71 bases at an 82 percent success rate to that point in his career, of his speed.

AP

9. Lloyd McClendon steals first base, June 26, 2001

Nearly two years after his ankle injury, Kendall was called out on a close play at first base leading off the bottom of the seventh inning of a 4-4 game against the Brewers in PNC Park’s inaugural season. Rookie manager Lloyd McClendon didn’t like the call, nor another at first base the previous inning, and came out to argue. After getting ejected by first-base umpire Rick Reed, McClendon pulled first-base out of the ground, tucked it under his arm, and headed up the tunnel with it. “I told him he wasn't using it, so I thought I'd take it,” McClendon said after the game. The Pirates, who had the worst record in the National League at the time, went on to win 7-6 in 12 innings. McClendon was fined $1,000 but not suspended for his theatrics. He was eventually fired during the 2005 season, the only time during their 20 years of losing that the Bucs changed managers at midseason.

10. Jason Schmidt traded, July 30, 2001 and Bronson Arroyo lost on waivers, Feb. 4, 2003

The Pirates had appeared to sell high in the summer of 2001 when they traded the 28-year-old Schmidt, a pending free agent, and late-blooming outfielder John Vander Wal to the Giants for 23-year-old rookie right-hander Ryan Vogelsong and extra outfielder Armando Rios at the 2001 trading deadline. Schmidt was a former prospect who had never lived up to his billing in the majors and had shoulder surgery in 2000, but he was coming off a string of six-strong starts in late July 2001. Little did the Pirates know he would build on that run by going 7-1 with a 3.39 ERA the rest of the way for San Francisco and two years later emerge as an All-Star and Cy Young runner-up.

Schmidt went to three All-Star games as a Giant. In 2003 he led the NL in ERA (2.34), ERA+ (180), shutouts (3) and winning percentage (.773 for a 17-5 record) and the majors in WHIP (0.95), and in 2004 he went 18-7 and struck out 251 men in 225 innings (10.0 K/9) while again leading the league with three shutouts. Altogether, Schmidt won 81 games after being traded. The Giants had to give him a four-year, $32 million contract after the 2001 season to get the bulk of those wins, but Schmidt earned that money and then some.

One of Schmidt's rotation mates was, briefly, Bronson Arroyo, another pitcher who achieved All-Star status after leaving Pittsburgh. To be fair, Arroyo never looked like much. He still doesn’t, in a way. He’s a lanky soft-tossing righty with unspectacular stuff and lousy peripherals and always has been. Still, after two seasons as a middling swing man for the Pirates, he put up a strong season in the hitting-friendly Triple-A Pacific Coast League in 2002, so when the Pirates tried to slip him through waivers just before spring training in 2003, the Red Sox snatched him up. Another strong season at Triple-A in his age-26 season put him in the rotation for what proved to be the first World Series-winning Red Sox team in 86 years in 2004, alongside Wakefield.

Arroyo has been one of the game’s most reliable innings eaters ever since, pitching the third-most innings in baseball since 2004 while winning 128 games for the Red Sox and Reds and posting an ERA just above league average in 10 seasons since being lost by the Pirates.

11. Bryan Bullington drafted first overall to cap a decade of bad first-round picks, June 2002

The blows from losing Schmidt and Arroyo might have been softened had the Pirates been able to replace them with young, talented pitchers from their bevy of high draft picks. And with all the losing the team did in the ‘90s, you’d think they would have at least done well in the draft. Not so. Between drafting Kendall with the 23rd overall pick in 1992 and Paul Maholm with the eighth-overall selection in 2003, the team made 12 first-round draft picks. Five of those choices never made it to the major leagues, and of the seven that did, five more failed to play above replacement level over the course of their very brief major league careers. Two of the five from that latter group, shortstop-turned-outfielder Chad Hermanson (10th overall, 1995), and righty John Van Benschoten (eighth overall, 2001), proved to be the team's least valuable hitter (-2.2 offensive wins above replacement as a Pirate) and pitcher (-3.7 bWAR), respectively, from 1993 to 2012.

The only two picks out of that dozen to have major league careers of any positive value were Kris Benson, the top pick in the 1996 draft, and Sean Burnett, the 19th pick in 2000. Benson was a highly-regarded prospect who couldn’t stay healthy. The lefty Burnett had a bit less regard and a bit less health but salvaged a career as a match-up reliever before injury struck again earlier this year.

Pittsburgh's biggest draft failure, however, was taking Bryan Bullington with the top overall pick in 2002 ahead of B.J. Upton, Zack Greinke and Prince Fielder, all of whom were taken among the top seven picks, as well as Nick Swisher, Cole Hamels and Matt Cain, who were taken in the second half of the first round. Bullington, a college pitcher selected at the top of the famous Moneyball draft, was supposed to be the safe pick, but he, too, got hurt, having labrum surgery in October 2005, which reduced his already limited potential. Bullington threw just 18 1/3 innings for the Pirates and didn’t pick up what remains his only major league win until 2010, when he was with the Royals. He has since found success with Japan’s Hiroshima Carp.

12. Randall Simon hits sausage with bat, July 9, 2003

AP

The Pirates and Brewers were locked in a tight 1-1 game in the seventh inning at Miller Park when it was time for Milwaukee’s famous sausage race. When the four sausages raced past the Pirates dugout, Bucs first baseman Randall Simon took a soft swing and hit the Italian sausage in the back of its big foam head, knocking the female runner inside the costume to the ground, and causing another contestant to trip over her and fall. It was a poor attempt at playful humor by Simon, but nobody got hurt beyond a scraped knee and maybe some hurt feelings.

Simon apologized and gave both aggrieved runners autographed bats, but the incident was blown out of proportion, prompting the first baseman to be arrested after the game and ultimately fined $432 for disorderly conduct and later suspended for three games and fined $2,000 by Major League Baseball. The Brewers won the game 2-1 in 10 innings.

13. Aramis Ramirez traded, July 23, 2003

Rated the fifth-best prospect in baseball prior to the 1998 season, Ramirez had a breakout year in 2001 at the age of 23, hitting .300/.350/.536 with 34 homers and 112 RBIs, but he fell off badly in 2002 due in part to an ankle sprain that bothered him all season. Arbitration pushed Ramirez’s salary to $3 million in 2003, and when he didn’t bounce all the way back to his ’01 level, the Pirates made him available at the trading deadline, ultimately dealing him to the Cubs with Kenny Lofton for Jose Hernandez, Bobby Hill and Matt Bruback. Ramirez immediately picked up his game with Chicago, and has hit .294/.357/.527 with 275 home runs and two All-Star appearances in 10-plus seasons since the trade.

14. 13-game losing streak, June 15-28, 2006

The worst losing streak the franchise has had since '93 saw Pittsburgh lose 13 straight games from June 15 to 28, 2006. The most remarkable thing about that streak was that the Pirates allowed an average of seven runs per game over its length, gave up 10 or more runs three times in four games in the middle of the streak and never once allowed fewer than four runs in any of those games.

15. Jose Bautista traded, Aug. 21, 2008

You can’t fault the Pirates for not expecting Jose Bautista to become one of the game’s best hitters any more than you can fault them for not expecting Tim Wakefield to win 200 major league games. Still, the success those players had after leaving Pittsburgh has to rank among the worst things to happen to the franchise in the last 20 years. Even for what Bautista was when they traded him -- a multi-position player with modest patience and power who struggled to hit for respectable batting averages -- the Pirates did poorly in this deal, getting only minor league catcher Robinzon Diaz in return.

Diaz has since passed through four other organizations, none of whom have given him a major league look. Bautista, meanwhile, has made four straight All-Star teams and hit 168 home runs in a little more than five seasons. He hit 97 of those homers in 2010 and 2011 combined, leading the majors both years, hitting 54 in the first of those seasons and posting a .302/.447/.608 bating line in the latter. As a Blue Jay, he has hit .262/.381/.542.

16. 105 losses in 2010

While Bautista was enjoying his breakout, 54-homer season, the Pirates hit rock bottom with a 2010 season that saw them lose 105 games, the most by the team since 1952. Contributing to that performance was an offense that scored just 3.62 runs per game, the team’s worst showing since 1985, and the worst single-season pitching performance by a Pirate in the last 20 years. The latter was turned in by Charlie Morton, who went 2-12 with a 7.57 ERA (53 ERA+) in 17 starts, averaging just 4.7 innings per start. The Pirates also suffered through a 12-game losing streak in June in which they averaged just three runs scored per game. Their summer of woe saw them go 23-57, a .288 winning percentage that translates to a 115-loss pace over a full season, in June, July and August.

However, the seeds of what would become this year's likely playoff team were already being planted. In addition to Morton, who has since had and recovered from Tommy John surgery, that year's club featured Andrew McCutchen, Pedro Alvarez, Neil Walker, Garrett Jones and Jose Tabata. Alvarez, Walker and Tabata were a rookies in 2010, and McCutchen and Jones were sophomores.

17. Brewers 20, Pirates 0, April 22, 2010

Early in their rock-bottom season, the Pirates suffered the most lopsided loss of their 20 years of losing, getting pillaged at PNC Park by the Brewers in a 20-0 rout. Prince Fielder started the scoring with a leadoff home run in the second inning and Ryan Braun hit a three-run shot in the third to put Milwaukee ahead 4-0. The Brewers broke it open with three in the fourth inning, put the game away with three runs in the fifth, turned it into a rout by plating six in the seventh and capped it with four more in the ninth.

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18. Pirates lose on a blown call in the 19th inning, July 26, 2011

On the morning of July 26, 2011, the Pirates were 53-47, six games over .500 and tied for first place in the National League Central, the latest they had had a winning record or a share of first place since 1992. That night, at Atlanta’s Turner Field, they jumped out to a 3-0 lead on the Braves in the first two innings, but the home team tied up the game with three runs in the bottom of the third. Fifteen scoreless innings followed, which were memorable primarily due to a young, impressively vocal Pirates fan sitting just behind the centerfield fence, and another fan’s impressive cup collection.

In the bottom of the 19th, Atlanta third baseman Julio Lugo drew a one-out walk and moved to third on a single by centerfielder Jordan Schafer. With no one left on their bench, the Braves had to let reliever Scott Proctor bat for himself. Proctor hit a ground ball to third baseman Pedro Alvarez. Lugo took off on contact, and Alvarez fired home. The ball got to catcher Michael McKenry just as Lugo reached the edge of the batting circle and began his slide. McKenry made a swipe tag that appeared to get Lugo on the right leg several feet ahead of home plate, but home plate umpire Jerry Meals called Lugo safe, handing the Braves a 4-3 win after six hours and 39 minutes of baseball. Meals admitted the next day that he had blown the call.

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The loss was also the longest of the Pirates' 20-year losing streak. Coincidentally or not, the team immediately went into a tailspin, losing 11 of its next 12 games and going just 19-42 (.311) over the remainder of the season, including an 8-26 (.235) skid from July 29 to Sept. 1. Pittsburgh finished 18 games below .500 and in fourth place, 24 games behind the division-winning Brewers and 18 games behind the wild-card winning Cardinals.

19. Seven errors, Sept. 7, 2012

The Pirates again found themselves leading the NL Central in July 2012. After spending six days alone in first place earlier in the month, they were still tied for first on July 18, and they were 16 games over .500 as late as Aug. 8. They collapsed again, of course, going 16-36 (.308) over the remainder of the season. For those unconvinced that they choked, see their 12-2 loss against the Cubs on Sept. 7 in which the Pirates made seven errors, their most since 1985, leading to nine unearned runs.

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20. No-hit by Homer Bailey, Sept. 28, 2012

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