By Eddie Small

Back when the Pittsburgh Pirates were still in the midst of the longest streak of consecutive losing seasons in the history of North American professional sports, I would often play a game with my friends who rooted for other baseball teams, informally known as “Who Has It Worse?”

I typically played this game with fans of teams that had a history of being good but not quite good enough to actually win a World Series, and the basic argument boiled down to whether it was more painful to root for a team, year in and year out, that never had a chance of doing even remotely well (the Pirates), or to root for a team that was expected to do well but collapsed at the end of the regular season or in the playoffs (pretty much every team that wasn’t the Pirates at some point between 1993 and 2012).

I likened it to choosing between either being single and lonely for your whole life or getting left at the altar on your wedding day.

Obviously, neither of those options are very appealing (both in terms of sports and relationships), but I was always adamant that I would prefer to root for a good team that collapsed over a team that was just straight-up terrible.

Part of this was a genuine belief that it would be more fun to at least have a reason to feel hopeful after April than it would be to lose interest in baseball after the season’s first two weeks, but there was a more selfish aspect to me advocating that viewpoint as well: between 1993 and 2012, it was all I had. Sure, the Pirates were never going to be good, but I could at least take some perverse type of comfort in knowing that it was harder to be a Pirates fan than it was to be a fan of any other MLB team, and I was not going to let anyone take that away from me.

And I still believe this. Although rooting for a notoriously terrible sports team does have its own weird, ironic type of fun, the Pirates’ return to relevance during the past three seasons has made it absolutely clear to me that it is much more fun to root for a team that actually has a chance of winning it all, even if the season still comes to a heartbreaking end.

But after last year, I am much more willing to acknowledge that these types of heartbreaking ends are still pretty rough.

Here’s a quick recap of the scenario the Bucs found themselves in at the end of the 2015 season (If I dwell on it for too long, I’ll become too angry to type).

The Pirates finished the season with the best record in baseball, except for one team. That team just happened to be the St. Louis Cardinals, who play in their division, meaning the Pirates were relegated to the one-game wild card playoff. They had to face Jake Arrieta of the Cubs, who was coming off one of the greatest pitching seasons in recent baseball history. The Pirates lost. Badly. So a season where they won 98 games ended in a short nine innings, one mistreated watercooler and one of the longest streams of curse words I have ever uttered.

This was the third year in a row that the Pirates’ trip to the playoffs ended quickly and the second year in a row they lost the Wild Card game, but to me, the 2015 loss is still the only one that really stings.

The team’s defeat in the 2013 playoffs felt different for two massive reasons:

1. I was still far too awestruck by the Pirates finally ending their streak of losing seasons to care very much about how far they went in the postseason.

2. They won the Wild Card game that year — the only series that’s decided in one game instead of at least five — and it turns out to be incredibly easy not to care about having to play in the Wild Card game if you win.

Their loss to the Giants in the 2014 Wild Card game felt a little more disappointing, but not by much, as I was still getting used to the team being good.

It wasn’t until last year that the Pirates managed to do something I didn’t think was possible after two decades of ineptitude: convince me they could maybe reach—maybe even win—the World Series. The days of being satisfied with a quick in-and-out postseason appearance were over. I was ready for more.

The problem was, I didn’t get it.

This is hardly a new issue for sports fans. I’m sure devotees of the Mariners still wonder how a team that won 116 games during the regular season could fall so quickly to the Yankees in the playoffs. And the team that was supposed to run roughshod over everyone in the MLB last year—the Nationals—didn’t even make the postseason.

But it is a new issue for me. Unrelenting awfulness has defined sports fandom for most of my life. An unquestionably great season that comes to such a quick, deflating end is a completely different kind of sports anguish, and I’m still learning how to cope.

I can’t express how badly I’d like the Pirates to win the division outright this year after three straight Wild Card games, but given that the Cubs spent the offseason acquiring Jason Heyward, Ben Zobrist and John Lackey and that #CardinalsDevilMagic is still a thing, I’m skeptical.

And part of me almost hopes that if they don’t win the division, they just don’t make the playoffs, sparing me the stress of having to watch them in the Wild Card game for the fourth year in a row.

But who am I kidding, I don’t mean that. A short playoff appearance is still better than no appearance. And after 20 consecutive losing seasons, could 20 consecutive Wild Card losses really hurt that much more?

Hopefully I won’t have to find out.

Eddie Small predicts that this year the Pirates will be shut out in the Wild Card game by Clayton Kershaw. He really does not like the Wild Card game. Follow him on Twitter: @Eddie_Small