When Pittsburgh last won

It's been 18 years since Andy Van Slyke chased down fly balls in the gap with the blend of instincts, speed and grace that earned him five career Gold Glove Awards. When Van Slyke isn't sharing opinions as a celebrity guest on St. Louis sports talk radio and keeping tabs on his son Scott, an outfielder with the Los Angeles Dodgers, he routinely encounters longtime Pittsburgh Pirates fans who come up and thank him for the memories.

"As a player, you don't realize how much of an impact you have on the culture in a city until you get away from it," Van Slyke said by phone. "Twenty years later, people tell stories about how they stayed at a rain-delay game for 2½ hours and you got a hit and sent them home happy, and they had to drive six hours and get up early for work on Monday. A girl in St. Louis told me she still has one of my old T-shirts from a Pirates team giveaway in her wardrobe. She doesn't wear it, but she still has it as a token of a memory."

This is the type of thrill that Jermaine Allensworth, Rob Mackowiak, Lastings Milledge and other Pirates of a recent (and sadder) vintage have not had the pleasure of experiencing.

The Pirates are about to dump a 20-year emotional anchor into the Allegheny River when they win their 81st game and break the longest streak of sub-.500 seasons by any team in North American professional sports history. Manager Clint Hurdle and his players are hosting a jubilee for Pirates fans who need to go back to the Willie Stargell-led "We Are Family" days -- and Roberto Clemente and Bill Mazeroski before that -- for true fulfillment and sustenance.

Andrew McCutchen and his teammates are also rekindling some pleasant memories for members for the 1992 Pittsburgh club, who are thrilled to relinquish the honor of being the last Pirates team not to be a drag on civic pride.

In the summer of '92, Pittsburgh was one of Major League Baseball's marquee franchises. The Pirates had a gruff, plain-spoken manager in Jim Leyland, a superstar left fielder in Barry Bonds and one of baseball's best starting pitchers in Doug Drabek. They survived the departure of star outfielder Bobby Bonilla to the New York Mets through free agency and posted a 96-66 record to win the National League East title by nine games over Montreal before falling a game short of the pennant against Atlanta.

The Pittsburgh players -- and the fans -- had no clue about the stunning array of mishaps, embarrassments and other indignities that would ensue over the next two decades.

Bonds departed for San Francisco as a free agent and the Pirates dipped to 75 victories in 1993, and the hits just kept on coming. Who can forget Derek Bell declaring "Operation Shutdown" in 2002, or Randall Simon making news the following year for taking a bat to a racing sausage in Milwaukee?

The Pirates whiffed on four-year contracts for Kevin Young and Pat Meares, and wasted first-round draft picks on Bryan Bullington, John Van Benschoten and Daniel Moskos. Manager Lloyd McClendon made the highlights by yanking first base from its moorings and carrying it down the dugout steps, and general manager Dave Littlefield essentially gave away Aramis Ramirez and Kenny Lofton to the Chicago Cubs in a salary-dump trade mandated by ownership.

The Pirates moved from sterile Three Rivers Stadium to scenic PNC Park in 2001, yet the losing persisted. Jason Bay, Brian Giles and Jason Kendall made All-Star teams and Freddy Sanchez beat out Miguel Cabrera for the batting title in 2006, but those players all fell victim to the malady that pitcher Jason Schmidt once dubbed the "Bucco Malaise." The Pirates suffered an additional jolt when Jose Bautista, a former Pittsburgh farmhand, emerged as a 50-home run superstar in Toronto.

All things considered, Pittsburgh fans and the players have endured a walk in the baseball wilderness of Biblical proportions. "Pops" Stargell, who died the day PNC Park opened, was World Series MVP when the Pirates won their last title in 1979.

"Let's put it this way: The last time the guys on 'Duck Dynasty' shaved is when the Buccos won the pennant," Van Slyke said.

Bonding through clubhouse hoops

To put all that suffering in perspective, it's instructive to reflect on the nonbaseball sporting developments that have taken place in the Steel City since the Pirates last posted a winning record:

• In 1992, first-year coach Bill Cowher led the Pittsburgh Steelers to an 11-5 record and a playoff berth. The Steelers have posted an aggregate record of 212-123 (for a winning percentage of .633), made the playoffs 14 times, won two Super Bowls and lost two others since the Pirates last broke the .500 barrier.

• Mario Lemieux, Kevin Stevens and Tom Barrasso led the Pittsburgh Penguins to their second straight Stanley Cup championship in 1992. Lemieux survived Hodgkin's lymphoma, entered the Hockey Hall of Fame in 1997 and was part of a group that bought the team two years later. The Penguins have posted winning records in 16 of the past 20 seasons, and won another Stanley Cup behind phenom Sidney Crosby in 2009.

• The Pitt Panthers have made 12 NCAA basketball tournament appearances since 1992. That includes five trips to the Sweet 16 and an Elite Eight appearance in 2009.

For those who prefer to mark their sports news through U.S. cultural signposts, "The Silence of the Lambs" was the big winner at the 1992 Academy Awards and Natalie Cole cleaned up at the Grammys. Some other 1992 news events: President George H.W. Bush took ill and vomited at a state dinner in Japan, Kurt Cobain married Courtney Love, Johnny Carson made his final "Tonight Show" appearance and gas cost $1.13 a gallon.

Reminiscing about the good old days is a labor of love for the old Pirates, many of whom are still in baseball in some capacity.

Leyland ranks 15th on the career managerial win list with 1,755 victories, and former catcher (and manager) McClendon and former coach Gene Lamont are part of his staff in Detroit. Dave Clark and Jay Bell are big league coaches, and Steve Buechele is a minor league manager with the Texas organization. Bob Walk and John Wehner, two other members of the '92 squad, are baseball broadcasters in Pittsburgh. A rookie pitcher named Miguel Batista made a two-inning cameo appearance for the Pirates in April of '92, and Kirk Gibson, now the Arizona Diamondbacks' manager, hit .196 in 16 games with Pittsburgh before being released that May.

Gary Varsho, a former backup outfielder and Leyland favorite, is now a scout with the Los Angeles Angels. He still remembers taking his post between innings at Three Rivers Stadium and seeing the same fan holding a sign with the inscription "Leyland's Bucs Play Hardball." The message resonated against its plain cardboard backdrop.

"I always took that sign personally," Varsho said. "We were proud to wear that uniform and win for that city. It's a different breed of cat in Pittsburgh. They expect hard-nosed players who play the game the right way. For them to go 21 years without winning -- that's tough."

The old Pirates were a talented group with a fun-loving attitude and camaraderie to spare. They gave players who made boneheaded plays a gold statuette known as the "Sammy Award," in honor of 1980s clubhouse favorite Sammy Khalifa. McClendon once received a Sammy Award for forgetting to leave tickets for his wife, and catcher Don Slaught snagged one for nearly batting out of turn. Leyland even captured a Sammy for being in the bathroom while Bonilla was nearly getting ejected in an argument with an umpire.

The entire Pittsburgh roster bonded through basketball. During the 1991 season, Van Slyke walked into the clubhouse one day with a tool belt and a saw and attached a small hoop to a pillar in the middle of the room, and the team's Around-The-World tournament was born. The Pirates used small rubber basketballs with Pizza Hut logos, and needed to keep spares handy because second baseman Jose Lind collected knives and liked to carve up balls that invaded his locker space.

Mike LaValliere, the squatty catcher from New Hampshire, beat Bonds, Bonilla and Van Slyke in the tournament before losing to outfielder Curtis Wilkerson in the finals. Randy Tomlin, a 5-foot-11, finesse lefty pitcher, won a second competition. It was a major understatement to say the tournaments were intense.

"They beat every Big Dance there ever was," said former Pirates coach Rich Donnelly, who is now a minor league manager in the Mets' organization. "Guys were so pissed off about losing in the Nerf tournament, they almost didn't want to go out and play a playoff game. I think Bonds lost to Van Slyke and didn't speak to him for the entire postseason."

That wasn't unusual. Bonds once referred to Van Slyke as "The Great White Hope," and the dynamic between the two All-Stars was frosty at best.

"Those two never spoke to one another except when Andy said 'I got it' in the outfield," Donnelly said.

Despair and, finally, renewed hope

The demarcation line between success and torture became official when the Braves' Francisco Cabrera singled home Sid Bream at Atlanta-Fulton County Stadium in the deciding Game 7 of the 1992 National League Championship Series. When umpire Randy Marsh signaled Bream safe, it set off a region-wide depression in western Pennsylvania. Given the economics of the game, the Pirates knew they were going to be challenged in keeping the roster intact. When Bonds left to sign a record six-year, $43.75 million deal with the Giants in December 1992, the slide unofficially began.

"Sid Bream slid, and the window slammed on our fingers," Van Slyke said. "There were babies born in Pittsburgh who went off to college and never saw their team win. In essence, they lost a generation of baseball fans."

Donnelly's son Bubba, a star basketball player at Robert Morris University in the early 1990s, took the loss particularly hard.

"I live in Ohio in the Tri-State area, and I know what it did to that city," Donnelly said. "It was like a death in the family. People had to get counseling. There were guys who had talk radio shows who couldn't even speak. We got on that plane home, and Andy Van Slyke called it 'the flight to nowhere.'

"Bubba cried so much that night, his eye got infected. He went to the eye doctor the next day, and while he was in the chair getting the eye exam talking about what happened, the doctor started crying. Then the nurses started crying too. It took the heart right out of everybody."

For a while, Pirates die-hards were hesitant to buy into the team's success this year for fear of having their hearts ripped out again. The Pirates enjoyed strong starts in 2011 and 2012 only to collapse in August and September, so the locals have reason to be dubious.

But the fans have gradually come around. Pittsburgh's average attendance of 26,787 is the team's largest since PNC Park's inception, and Hurdle regales reporters each day with tales of the warm receptions he gets during sojourns to the local Starbucks and Giant Eagle grocery store.

The Pirates, in the middle of a big series with St. Louis this weekend, have sputtered of late and are taking a bit longer than expected to reach 81-81 and make a .500 season official. But it's only a matter of time. Can they parlay the magic of this season into something more than a quick one-and-done in the NL wild-card play-in game? That's the next big question.

LaValliere, who lives in Bradenton, Fla., sensed the Pirates were ready to take a step forward when he spent nearly two months helping coach Jeff Banister work with the team's catchers in the Grapefruit League.

"At the end of spring training, they sent some major leaguers down to Triple-A," LaValliere said. "In years past, they had Triple-A guys playing in the big leagues. That was the tipoff to me that they had a solid team. They were so much deeper and had so many good arms, I'm not surprised about what's happened. Personally, I'm not looking for them to break any losing streak. I'm looking for more."

At the very least, the end of that humiliating 20-year futility streak will be cause for Pittsburgh baseball fans to crack open an ice-cold beverage and celebrate. As Donnelly points out, no team has ever won a World Series with a losing record.

"I've been a Pirates fan since I was 5 years old, and I know one thing," Donnelly said. "The day they go over .500 or win the pennant -- or both -- there's going to be a lot of Iron City flowing."