PITTSBURGH: The Pirates had just returned home from an eight-game losing streak last week. The usual gaggle of scouts could be found sitting in the seats behind home plate at PNC Park watching the home team face the Cardinals. The skid had dropped the Pirates seven games under .500 and seemingly on their way to a 17th consecutive losing season, which would break their tie with the 1933-48 Philadelphia Phillies for the longest stretch of sustained futility in major American professional sports history.

Among the scouts watching that night were Cam Bonifay, working for the Reds, the Cubs‘ Dave Littlefield, and Roy Smith of the Blue Jays. This was more than a little ironic. Bonifay took over as the Pirates’ general manger for Ted Simmons midway through the 1993 season. Littlefield replaced Bonifay midway through the 2001 season and stayed on the job until being fired late in the 2007 season. Smith served as the assistant GM under both Bonifay and Littlefield. Thus, nobody has been more responsible for all of the losing, which began in ’93, than this trio.

It is now the charge of club president Frank Coonelly, GM Neal Huntington, and manager John Russell, who are in their second season running the club, of digging out of a hole just slightly more shallow than the Grand Canyon. The Pirates have few impact players on the major league roster, and even fewer top prospects in the farm system following years of drafting on the cheap and ignoring the international free-agent markets.

While the moves of Bonifay and Littlefield became laughable at times, the moment that signaled the start of all the losing was a heartbreaker. The Pirates won three straight National League East titles from 1990-92, quite a turnaround for a franchise that nearly left town in 1985 until Pittsburgh mayor Richard Caligiuri put together a public/private consortium to buy the club. However, they failed to make it to the World Series in any of those three division-winning seasons, and the final defeat was incredibly difficult.

That was the game in which the Braves scored three runs in the bottom of the ninth inning of Game Seven of the 1992 NLCS to rally for a 3-2 victory. Popular former ex-Pirates first baseman Sid Bream (who still lives in Pittsburgh) slid home with the winning run ahead of Barry Bonds‘ throw. The winning single was hit by a nondescript bench player named Francisco Cabrera off of Stan Belinda, a fresh-faced reliever who grew up in rural Port Matilda, PA, dreaming of pitching for the Pirates in the World Series.

Bonds left as a free agent after that season and so did ace pitcher Doug Drabek, a year after slugger Bobby Bonilla bolted and 20-game winner John Smiley was traded before he could follow suit. In their stead, the Pirates hoped to rebuild quickly around a number of young players: first baseman Kevin Young, second baseman Carlos Garcia, left fielder Al Martin, left-handers Steve Cooke and Denny Neagle, and knuckleballer Tim Wakefield. All except Neagle and Wakefield turned out to be journeymen, and the Pirates released Wakefield in 1995 during spring training, deciding that Wakefield had lost the feel on his knuckler. Of course, he is now in his 15th season as a mainstay of the Red Sox‘s rotation.

Releasing Wakefield was just one of many bad personnel decisions made by Bonifay. Another doozy came in 1999, when he signed infielder Pat Meares to a four-year, $15 million contract extension. Meares already had sustained a wrist injury that robbed him of what middling power he possessed. Furthermore, Meares had been so lightly regarded after being released by the Twins the previous winter that the Pirates were the only team to offer him a big-league contract as a free agent. It was no wonder he had a look of amazement following his signing of the four-year deal. “This really surprises me,” he said.

Bonifay’s last stand came at the 2000 Winter Meetings in Dallas. Knowing they would have a bump in revenue with the opening of PNC Park in 2001, the Pirates decided to be players on the free-agent market. The problem was that they gave much of their money to washed-up outfielder Derek Bell, who became a monumental bust and half-stepped it through only one season of his two-year, $9.75 million contract. Making matters worse, manager Lloyd McClendon said the Pirates “sent shock waves through baseball” by signing Bell. McClendon apparently missed that the Rangers lavished a then-record $252 million on Alex Rodriguez at the same meetings, while the Rockies spent $173 million on Neagle and fellow lefty Mike Hampton. The only thing shocking was Bell’s horrible performance. He hit .173 in 46 games in 2001, and was released the following spring after infamously telling a reporter he would go into “Operation Shutdown” if he was not the right fielder on Opening Day.

After Littlefield, Bonifay’s replacement, had jettisoned Bell, it was almost all downhill, as his tenure was fraught with so many awful player moves that he made Bonifay look like Branch Rickey. Littlefield’s last move was his most costly as he inexplicably traded for Giants right-hander Matt Morris, who was clearly on his last legs. The Pirates took on $13 million by acquiring Morris. For that money, he won three games in 16 starts before being released by Huntington early last season.

There were plenty of other gaffes, none more publicly humiliating than when five of the first six players taken in the Rule 5 draft at the 2003 Winter Meetings in New Orleans were Pirates. A ballroom full of baseball people broke into laughter over that. Also in 2003, the Pirates placed promising young pitcher Bronson Arroyo on waivers and he was claimed by the Red Sox. Three years later, while pitching for the Reds, he was selected to the All-Star Game. Fittingly, the game was at PNC Park, and Arroyo was booed during pre-game introductions. “I didn’t take it personally,” Arroyo said of the fan reaction. “They were just booing because the Pirates are the most inept organization in baseball.”

Not every player was down on Littlefield, however. He signed Jeromy Burnitz to a one-year, $6.5 million contract as a free agent prior to the 2006 season; the veteran outfielder sleepwalked his way to a .230 batting average and then never played again. Burnitz approached Littlefield as the GM walked through the clubhouse on the final day of the season and enthusiastically shook his hand. “Dave,” Burnitz said, “I can’t thank you enough.”

Even Bream returned to the Pirates last season as the hitting coach with their short-season A-ball State College team in the New York-Penn League. Part of the reason he came back was to help exorcize the ghosts of losing, a haunting that began when he slid across home plate that fateful night at Fulton County Stadium in the latter days of the original George Bush administration. “I’d like to try to help change things,” Bream said.

State College went 18-56 for the worst record in professional baseball. Beaten down by the losing, Bream chose not to return this year.

A version of this story originally appeared on ESPN Insider Insider.