Pittsburgh — 

Pittsburgh baseball first broke Don Kelly’s heart in the early ‘90s. And those were in the good years.

Born months after the team’s last World Series win in 1979, Kelly was 10, 11, and 12 years old when the Pirates won three consecutive division titles, only to fall short in the postseason each time.

What followed was 20 years of futility. Two decades of finishing below .500, heading home long before the serious contenders began their October hunt for a ring. Somewhere along the way, billionaire Bob Nutting became the team’s principal owner.

By 2013, Kelly, the kid from a small city about 35 miles north of Pittsburgh, was a major leaguer playing for the Detroit Tigers. Even then, he was still rooting for the Pirates “156 out of 162 [games], except for the six games that we played against them,” he told CNN Sports.

That October, while he was playing for a different team, was Kelly’s favorite moment as a Pirates fan. True yinzers already know where this is going: The 2013 National League Wild Card Game, where 40,000 Bucco faithful rattled the opposing pitcher Johnny Cueto so thoroughly with their roars that he dropped the ball, and gave up a game-changing home run on the next pitch.

“You could feel the energy through the TV,” Kelly said.

When Kelly says the Pittsburgh fanbase is a “sleeping giant” ready to wake, he speaks from experience. The 2026 club just might be the team that rouses them.

At the very least, they have a better chance than any other recent iterations of the franchise. All it took was the reigning Cy Young Award winner, the largest free-agent contract ever given to a position player in Pittsburgh and a top prospect locked up with a nine-figure extension.

PNC Park could be full again. Fans might arrive with traffic cones on their heads this time (yes, really, we’ll get to that). It isn’t quite happening yet, but it could be.

“For me personally, that’s what drives me,” said Kelly, now in his first full season as the skipper of his hometown Pirates. “I love the game, I love the guys in the clubhouse, and I love the city of Pittsburgh.”

The question now is: Can the city of Pittsburgh remember how to love the Pirates?

The wind chill temperature on a misty morning before a mid-week day game near the Allegheny River was 37 degrees. Still, nearly two hours before first pitch, a gaggle of kids and their parents pressed against the netting near the Pirates dugout, clamoring for Konnor Griffin.

Griffin, 20, is closer in age to these kids than some of his own teammates. He initially ducked into a nearby stairwell, stone-faced. The fake-out is only a fraction of a second before he’s back, signing baseballs, hats, one cast, and a jersey with his name and number on the back.

“It’s really hit me lately: A lot of No. 6s running around in the stands, and it’s pretty cool,” Griffin told CNN Sports. “I want a lot of people to wear my jersey, so I want to continue to play well.”

He had played just 25 big-league games when he said that. To be honest, it isn’t so much his performance that inspired strangers to wear his number and shout his name; it’s his promise – both the potential he possesses and the commitment he made to stay in the city.

Griffin entered the season as a consensus No. 1 prospect in the sport. Drafted in 2024, he rocketed through three minor league levels last season and inspired speculation he could break camp with the big-league club as a teenager this spring. Instead, he spent five games in Triple-A before making his major league debut in front of a sold-out crowd for the Pirates’ home opener on April 3.

His promotion was met with rumors of an impending extension, and it didn’t take long for one to materialize: nine years, $140 million (with escalators that could bring it to $150 million). It is the largest contract in Pirates history by every metric – total value, average annual value, and years. Griffin – 6-foot-3-inches tall and all muscle, a five-tool shortstop – is now tied to Pittsburgh through at least 2034.

Fans buying his jersey are buying into an idea: that the next decade of Pittsburgh baseball will be better than the last. Fandom is more fun if you believe, and so, they are starting to believe.

“We haven’t been to the playoffs in a lot of years, so that’s the goal, to get back there,” Griffin said.

He’s a good ambassador for saying “we” about losing that happened when he was in middle school in Mississippi.

“I haven’t been a part of those teams, but you can still feel it, there’s a little pressure. Like, hey the city wants to see us win. Like, we gotta win. It starts this year.”

A complicated dynamic between team, city and owner

As one of baseball’s oldest franchises – and a participant in the first-ever World Series well over a century ago – the Pirates have become mired in something worse than mediocrity: hopelessness. It has been a decade since their last playoff appearance and more than 30 years since they played for a pennant.

Fans are not just sad, they are angry. They frequently implore Nutting – via ballpark chants and billboards and banners flown behind planes – to “sell the team.”

Their frustration is justifiable. Over the past decade, the Pirates have consistently had a bottom-five payroll. Fans were mad because the team wasn’t winning and the owner wouldn’t spend to make them better.

That trend – the losing and the low payroll – persisted through the first two seasons of the already remarkable career of Paul Skenes. Skenes arrived in the majors already famous – for his pitching and his personal life – and then he won Rookie of the Year in his first season followed by the Cy Young Award in his second.

Skenes’ success was met with industry-wide assumption that Pittsburgh would eventually be just a mere footnote in his Hall-of-Fame plaque. Good players leave when they can or get traded even sooner. Pittsburgh, for a long time, was not a place where players came to win. Or it wasn’t, for a while.

The change began over the winter when the Pirates were reportedly in on enough big free agents and spending enough (relative to their own recent history) that it was even a little suspicious. That spending spree pulled their 2026 payroll all the way up to 22nd in baseball.

They traded for Brandon Lowe, who made the postseason five consecutive years with the Tampa Bay Rays. They signed Ryan O’Hearn on the largest free-agent contract the team has ever given a hitter – all of $29 million over two years, an amount that could be found in the couch cushions at Dodger Stadium or Citi Field – and Marcell Ozuna. They bolstered the bullpen with proven relievers.

And, of course, Griffin, who became “The One That Stayed,” before he had even a month of major league service.

“I saw potential for a team that was ready to break out,” O’Hearn says of why he picked Pittsburgh. “I thought that I could add to the offense and potentially do something special here.”

It has worked early on. Lowe has already matched last season’s home run total out of the second base position for the Pirates in just 27 games. O’Hearn has been 50% better than the league average on offense. Griffin had an RBI double in his first big-league at-bat and a home run on his 20th birthday.

And all around the ballpark, fans show their emotional investment with orange traffic cones – printed on shirts, turned into hats, tiny ones hung on earrings, and full-sized ones heaved unwieldily around the stands.

Why traffic cones? It’s not fully clear. It’s because of a misprinted T-shirt or an analogy about capitalizing when there’s traffic on the bases or else a fortuitous confluence of the two, but somehow traffic cones became a rallying cry in Pittsburgh. It’s an organic, goofy, good-vibe celebration that binds the players and the fanbase.

This is what a team with enough talent on it to conceivably win does for a city, it lets them believe that the intangibles are what make the difference.

“I’ve heard a lot of people who have been around in this organization for years saying, like, ‘It’s different this year. It’s different this year.’ And that’s cool to hear. For me, it’s pretty simple: We have a good team, and fans want to come out and see a good product on the field,” O’Hearn says.

“You invest in the team and make good things happen, right?”

Hope is a hard thing to catch and harder to keep

In the days after Pittsburgh hosted the NFL Draft, baseball was just part of the Steel City’s sporting milieu.

Local businesses still had football-inspired specials advertised in the windows downtown. The Pittsburgh Penguins, who had fallen down three games to none in the opening round of the Stanley Cup playoffs against their cross-state rival Philadelphia Flyers, had surged back to make a series of it with consecutive wins.

And the Pirates had better than a coin-flip chance to make the playoffs, according to FanGraphs. They started the season at 45.3%, the highest preseason chances since the site began tracking in 2016. Through the first month, those odds only climbed.

All of that came together to give Pittsburgh sports fans that most wonderful of things: hope. The Pirates – residents of one of the most picturesque ballparks in the country – specifically seemed primed to step into the spotlight. Even the hard feelings around Nutting seemed to be easing after the promise of bigger spending, better players and – presumably – a bunch more wins.

But then the Philadelphia Eagles swooped in and stole a draft pick while he was literally on the phone with the Steelers. And the Penguins fell to the Flyers in overtime and were eliminated. That loss came less than an hour after a would-be walk-off home run landed safely in an outfielder’s glove for the final, sealing the Pirates’ then-fourth consecutive loss.

If the first month of the season is a small sample, a single series is essentially meaningless. Still, watching the Pirates get mopped – losing every game of a four-game series – by their division rival St. Louis Cardinals (playoff odds to start the season: 8.5%) felt like Pittsburgh had replaced the pain of not having hope with the pain of having it unmet.

“Playoff odds don’t mean anything if we don’t play well,” Skenes told CNN Sports after a rare clunker from the ace led to their fifth-straight loss.

Lowe said that even when things were going well, he and the other new additions have used their experience winning elsewhere to talk to their new teammates about losing. To prepare them for a season spent under the auspices of a real shot at something good, they have to know how to weather the losses.

“‘Hey guys, we’re gonna lose,’” Lowe says he’s told his teammates. “And crappy as it is, and everybody hates to lose, nobody likes it, it’s part of the game. We’re gonna fail. We’re gonna have days, man, we suck that day. … There are going to be bad days, but you can’t focus on it. You have to come back, wash it, be ready to go the next day.’”

That mentality is a baseball cliché, but for a team trying to change its fortunes, it’s critical. How do you distinguish between a team that is losing, and a team that is losers?

“We know we’re a good team,” Skenes says. “We’re not going to let five games affect us or change the way we see ourselves.”

And they didn’t – outscoring another division rival, the Cincinnati Reds, 27-8 in a three-game sweep starting the very next day. This is a funny thing about baseball, day-to-day, it can be hard to see who a team really is. Any true fan will tell you it takes a long time for a team to earn their trust. As with anything, it’s easier to lose faith than to find it again.

But the formula is simple, if not easy to execute: sign good players, and then win more baseball games.

For the first time in a while, the Pirates seem committed to the former. It’s enough to convince fans to take a closer look, but it wil take results to truly change their minds.