By Hannah Keyser, CNN
Pittsburgh (CNN) — 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?
Prospects bring promise
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