The Pittsburgh Pirates are learning something in real time about Don Kelly: creativity as a manager is a lot more fun when it works.
For eight innings Monday night at PNC Park, Kelly looked brilliant. The Pirates pieced together one of the most fascinating games of the season, using opener after opener, mixing matchups, and riding electric rookie stuff to completely suffocate the St. Louis Cardinals lineup.
Mason Montgomery opened. Justin Lawrence followed. Wilber Dotel overwhelmed hitters with triple-digit fastballs. Evan Sisk handled leverage innings cleanly.
Twenty Cardinals came to the plate. Twenty Cardinals went down. The Pirates were nine outs away from a combined perfect game in a bullpen game. It was the kind of night that can make a modern manager look ahead of the curve. It was aggressive, unconventional and fearless — all qualities Pirates fans have begged to see from this organization for years.
And then came the ninth inning. The 4-2 collapse against the Cardinals was brutal not simply because the Pirates lost, but because it exposed the razor-thin margin Kelly willingly creates when he manages this way.
This is the balancing act he has chosen.
Don Kelly's creative pitching strategy backfires in Pirates' ninth-inning collapse vs Cardinals
Despite possessing one of the most talented rotations in baseball — a group headlined by Paul Skenes and backed by Mitch Keller, Bubba Chandler and Braxton Ashcraft — Kelly has repeatedly shown a willingness to steal innings with bullpen games, openers and hybrid pitching plans.
Sometimes it is about rest. Sometimes it is matchup-based. Sometimes it is clearly organizational caution with workloads in April.
The logic makes sense, but bullpen games also require perfection. You do not have much room for one reliever to simply have an off night — and that reality hit hard Monday.
Dotel, especially, looked like a revelation. In just his third major-league appearance, the rookie threw four overpowering innings while averaging 99 mph on his fastball and still touching upper-90s deep into his outing. For a while, he looked like the latest example of Pittsburgh’s suddenly elite pitching development pipeline.
Kelly pushed exactly the right buttons for most of the evening. Until the final one.
Dennis Santana simply did not have it. Pedro Pages ambushed him. JT Wetherholt tied the game moments later. Then came the walks, the traffic and Jose Fermin’s crushing two-run double down the line. Game over.
Dennis Santana on a tough outing after blowing game and bouncing back. — From Eric Bowser in Pittsburgh pic.twitter.com/sGmw2BBbzw
— DK Pittsburgh Sports (@DKPghSports) April 28, 2026
That's where Kelly’s growing pains as a manager become visible. The process was defensible. Maybe even smart. But managers are ultimately judged by feel as much as logic, and Monday’s game invited the obvious second-guessing.
Should Dotel have started the seventh instead of turning it over to Sisk? Should Santana have entered with a cleaner leash after recent inconsistency? Should the Pirates have been running a bullpen game at all when the rotation is supposedly the strength of the roster?
These are fair questions, even if none have easy answers. That is the burden of managing creatively. When it fails, every decision suddenly looks overcomplicated.
To Kelly’s credit, though, the postgame reaction inside the clubhouse did not sound fractured. Santana owned the loss. Kelly defended his pitchers. Nobody panicked. The Pirates largely executed the plan they intended to execute.
Kelly is still establishing his managerial identity. He is not trying to survive games. He is trying to modernize how the Pirates deploy pitching. Some nights, that approach is going to look innovative and brilliant. Other nights, like Monday, it is going to look maddening. That is part of the learning curve.
And honestly? The Pirates probably need to live through some of these painful losses now if they are serious about building something sustainable for October. Postseason baseball increasingly demands flexibility. Bullpen games happen. Openers happen. Hybrid outings happen. The old-school model of asking starters for seven innings every night barely exists anymore.
Kelly clearly understands where baseball is headed. Now comes the harder part: learning exactly when to trust the process and when to simplify things before a game slips away.
