Following just a little more than a year of failure and futility, beginning in September, 2011, and running through all of last season, most Boston Red Sox fans I knew, myself included, felt like this. After all those Bambino-cursed decades spent earning a real reputation for hard luck, we tarnished the legacy of dignified loserdom in one downward swoop, denouncing the team and foisting shame on the graves of our better forebears by becoming the most dreaded of dreadful sports-watchers: the fair-weather fan. But, being an admitted fair-weather fan, I can now say that the skies sure do look clear right now, what with the Sox easing nicely toward the playoffs and featuring a roster of truly lovable players. The birds are singing around Boston, sounding as if they might skip heading south this year altogether. Of course, no one south of Hartford wants to hear anything of it; nor should they have to. Sox fans endured a mere thirteen months of losing baseball before getting a winner again. Dispiriting, for sure, but how about living through two hundred and forty or so months deep in the weeds below .500? Now that sounds like a curse.

Two hundred and forty months—twenty consecutive seasons—is the length of time that fans of the Pittsburgh Pirates were condemned to root for a losing team. And their last winner, the 1992 squad, didn’t exactly end on a high note: going into the bottom of the ninth in Game 7 of the National League Championship Series against the Braves, they were just three outs from the World Series—and then they blew a two-run lead. After that, things managed to get worse. In the course of two decades, the team lost more than a hundred games twice, and never won more than seventy-nine. Baseball seasons are long enough in the best of times. In the worst of them, when a team reveals itself to be unworthy of the playoffs by May, they are really long, hopeless affairs. Fans can be forgiven for losing interest. This past Saturday, the Houston Astros reportedly attracted just a thousand total television viewers for a game against the Angels. And who can blame those who didn’t bother to tune in? The Astros are nearly forty games out of first place.

But, for the Pirates, the dismal, meaningless Septembers are now a memory. This season finds them vying for first place in the National League Central, just behind the St. Louis Cardinals. And even losing three of their last four, they still have a better than ninety-nine per cent chance of making the playoffs, according to ESPN. On September 10th, the team won its eighty-second game, ensuring that, no matter what else happens, it will finish the year with more wins than losses.

Earlier this week, I spotted a man in a Pirates hat sitting on a bench near my apartment. Thinking we had something in common, fans of winners now, I pointed to his head and congratulated him on his rewarded fandom. How does it feel, I asked? “Surreal,” he said. And then, expecting him to say how much he wanted his team to win it all, to make up for all the losses he’d suffered through the years, I asked what he hoped for from the playoffs. World Series or bust, right? “You know,” he said, “even if they just make the Wild Card game and lose, that’d actually be fine by me.” Where was this fair-minded composure coming from? Hadn’t the Pirates been a bunch of bums for years, and didn’t they now owe their fans an ultimate victory? This man would not fit in among Red Sox fans. And, for a moment, I was abashed, until I thought about how great the Sox were doing, and whom they would decide to pick as their fourth starter for the playoffs, and wouldn’t another parade be great…

Later, I came across a blog post that Charlie Wilmoth, who runs Bucs Dugout, the Pirates site at SB Nation, had written on the night that his team made it to eighty-two wins. In it, he wrote about the frustrations that he had experienced in nine years of writing about the team, and about feeling “unburdened” after finally seeing a winning season. He also wrote, “I learned to take pleasure in smaller things than victories, and in vague dreams about the future, and I could do it even when the Pirates didn’t win.”

I thought back to that Pirates fan I’d met in my neighborhood. He’d seemed happy about baseball in a way that I hadn’t for years. Perhaps the sustained bout of losing had made people like him and Charlie Wilmoth into a better breed of sports watchers—not grasping and, as my colleague Nicholas Thompson recently noted of Sox supporters, entitled, but instead, thanks to all those years of forced letting go, the possessors of at least a minor kind of baseball enlightenment.

This week, I asked Wilmoth if his life had gotten better during this winning Pirates season. “It’s great to go to Pittsburgh and feel the excitement in the air. And winning that eighty-second game was a palpable relief,” he wrote in an e-mail. “But I think my happiness or unhappiness is mostly predicated on more personal things, like what I’m doing for work, or my relationships with other people…. I like feeling excitement over a big win, but it’s bad to let a sport you watch affect your day-to-day mood too much. As a Pirates fan, that’s a lesson I’ve learned over twenty years. I’m thirty-three, and being a Pirates fan has, on some level, been miserable since I was in middle school. If I couldn’t compartmentalize my feelings about the Pirates, I would have spent a quarter of my life being a miserable person.”

Wilmoth forwarded the questions I’d asked him to some of his colleagues. Was life better?

“As a fan and someone who watches games for a living, I generally enjoy the games and the season either way, maybe incrementally more if they are winning,” wrote David Todd, the drive-time radio host on 970ESPN, in Pittsburgh. “But the team winning makes me meaningfully happier because it makes so many people I come into contact with happier.”

And Wilbur Miller, who contributes to Bucs Dugout, said, “I expected it to be a sort of giant relief, a lifting of a big weight, and that’s exactly what it’s been. One thing I didn’t expect, though, was the fact that it literally takes some getting used to doing things like scoreboard watching in September.”

The Pirates’ offense has stalled this month. Their lead in the Wild Card race is slimming, though it appears likely to remain intact just long enough. And even Wilmoth, seemingly at peace with his Pirates, feels the pull of some darker instincts. “The Pirates were sixteen games above .500 at one point last year, and, intellectually, it would have been ridiculous to believe anything other than that they’d have a winning season” he told me. “But emotionally, as a Pirates fan, you’re thinking, It’s the Pirates, so they’ll find some way to blow this. And, sure enough, that’s exactly what happened.” The team ended last season with a record of 79-83.

“I remember thinking the same thing when I was watching the 2004 World Series, incidentally—that Doug Mientkiewicz was going to drop the final out and the Red Sox were going to find some spectacular way to blow the World Series,” Wilmoth added. “That didn’t happen, of course, which shows how silly that way of thinking is, and, as a baseball writer, I obviously don’t approach things from a superstitious perspective. But as a fan it’s a hard habit to break, especially when it’s developed over twenty years.”

Photograph: Justin K. Aller/Getty.