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After 20 Years of Waiting, a Winning Season is Within Reach for Pirates Fans

The year 1992 was an exceptional time to be a sports fan in Pittsburgh.

The Steelers finished first in their division, the Penguins won the Stanley Cup and the Pirates made it to the playoffs. Little did baseball fans know then that it would be two decades before the Pirates would have another winning season.

Now the Pirates are a handful of games away from ending the skid.

The Pirates hold the record for most consecutive losing seasons in all professional sports in U.S. history — the kind of streak that can only be achieved through a harmonic convergence of failure, said long-time Pittsburgh Post-Gazette sports columnist Gene Collier.

He reeled off a list of what he thinks are contributing factors: new owners who were out of their depth, a lack of management talent in the front office, potential stars who failed to develop during their time with the team, and the empty promise that a new stadium would help the Pirates attract top-tier talent.

PNC Park, built in 2001, has yet to host a winning season.

“And then there was a lot of bad luck too with injuries and hiring," Collier said. "And then they kind of retained this aura of cheapness."

Over much of the past two decades the Pirates ranked among the bottom five teams for spending on player payroll.

Despite the team's decline, a hardcore — some would say masochistic — group of fans continued to pay close attention to the Pirates.

Freelance writer and blogger Matthew Wein is among them. He said enduring all those losses made him appreciate the precious victories and well-executed plays, when the Pirates produced them.

“What you ultimately live for as a Pirates fan for the last 20 years, is the series of really quick moments where you get the satisfaction of that amazing, amazing win,” he said.

For Wein, being a die-hard fan comes with die-hard trappings: a secret parking spot, a special arrangement with the usher to sit with your clan near the first base line for the price of general admission. And because wins were uncommon, tickets have been cheap and available over the years. This season there are fewer empty seats at the ballpark.

“I feel like I’ve been a part of a very, very exclusive group of people, and all of a sudden the bandwagon potential is tremendous, to the point where it’s unsettling," Wein said.

And it seems a bit unfair to Wein. He has stuck with the team through the deepest of the doldrums, and now he is just another guy in a Pirates shirt. So he decided to let his shirt do the talking. Wein wears the jersey of pitcher Ryan Vogelsong, a player he never liked, who failed to do well as a Pirate. He thinks the jersey epitomizes his loyalty to the team during its record slump.

“I want people to know I was there," Wein said. "All those years, I was there. You can claim to have been there, you know you weren’t, but I know I was.”

Collier was also there, but he didn't enjoy writing about a losing team season after season. He said years would go by where he would only write a handful of columns from the ballpark because the story never changed. Now, he said it is pleasure to write about the team.

“The last three years have really been great," Collier said. "I’m just speaking personally. It’s just been so much easier for people like me because the Pirates are topical. They’re topical in June, July, part of August, and it’s been great.”

Collier tries to put the last two decades into perspective.

“I think they’re really deep in the social fabric of this city and people listening on the radio," he said. "There’s been a ton of excellent baseball. In 20 years of losing, the Pirates are still a winning organization all time.”

After more than a century of baseball, the Pirates are still hundreds of games above 500. This year they will add to that winning statistic while ending a losing one.

Larkin got her start in radio as a newsroom volunteer in 2006. She went on to work for 90.5 as a reporter, Weekend Edition host, and Morning Edition producer. In 2009 she became 90.5's All Things Considered host, and in 2017 she was named Managing Editor. She moderates and facilitates public panels and forums, and has won regional and statewide awards for her reporting, including stories on art, criminal justice, domestic violence, and breaking news. Her work has been featured across Pennsylvania and nationally on NPR.
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