The Cold-Calling Mayor
Why Pittsburgh stopped waiting for the big companies to show up
Most big-city mayors don’t cold-call companies. There’s no need to. The big cities like New York and Chicago have inbound demand, site selectors who already know the address, and a gravity that does the work for them. Corey O’Connor doesn’t have that same gravity in Pittsburgh, so he picks up the phone.
I sat down with Pittsburgh’s mayor in his sixth-floor office this spring, while reporting on my forthcoming book on what makes some American cities prosper, and others falter. His office is an archive of the city’s past—old photographs, a podium from the first city hall, a portrait of his father, Bob, who held the same job and was known as “The People’s Mayor.” But the thing I kept coming back to afterward wasn’t what was on the walls. It was the standing appointment on his calendar.
Every week, the mayor’s office conducts 10 company calls with firms around the globe, which O’Connor leads personally. Some recipients think it’s a prank, but once they realize it isn’t, he told me, they’re mostly just grateful anyone called. The pitch isn’t a tax abatement or an incentive package. It’s the city itself, delivered as a question: Why are you not in Pittsburgh?
It’s a small thing that reveals a larger strategy. O’Connor has given up on the move that Pittsburgh, and many cities like it, have spent decades chasing: the one giant employer that relocates, builds a campus, and fixes everything at once. “It’s coming, it’s coming, and it never happens,” he said. “So why not pick off the five jobs here, the ten jobs here?” Five jobs may not sound like much, but tens of thousands of them, accumulated over a term, are a diversified economic strategy.
The reason the calls land more than not is that almost everyone, somewhere, has a Pittsburgh tie. The Carnegie Mellon graduate who decamped to Silicon Valley. The kid from the South Hills who is running a startup in Austin. The tech CEO whose mother, O’Connor noted, has been guilt-tripping him to bring jobs home. When the steel industry collapsed two generations ago, hundreds of thousands of Pittsburghers scattered across the country—and, as economic development director Steve Wray put it to me, they carried the city with them. “You’re selling it (Pittsburgh) whether you know it or not,” he said.
That sentence stuck with me because it points to something most economic-development playbooks miss. The departure of people was the real loss. The attachment that survived the departure might be the asset. Wray, who helped lift student retention from 30% to 50% in a previous job in Philadelphia, is now trying something similar in Pittsburgh—treating the region’s 100,000 students at its colleges and universities as a four-year test drive, and the far larger diaspora as a population the city already owns and has barely begun to call home. Wray is a three-time returner himself: grew up here, left, came back, left again for twenty-eight years in Philadelphia, and came back three years ago. Pittsburgh’s pull is real. The open question is whether it’s strong enough to move the numbers that matter.
And there are numbers that matter, more than the comeback story usually admits. Pittsburgh ranks 40th of 250 metros on The Geography of Prosperity Index, a new tool I co-created to measure prosperity without leaning on the usual economic indicators—and the interesting part isn’t the city’s rank. It’s that Pittsburgh scores near the top of the country on some dimensions and near the very bottom on one in particular, the one that’s hardest to change: population stagnation. The cold calls, the student and diaspora outreach: they’re all quietly aimed at recruiting people to Pittsburgh or retaining them there.
What I can say from the office that morning is that O’Connor doesn’t talk like a man waiting to be rescued. He rightly boasts about the city’s assets. He talks earnestly about the things he’s done already, like relighting the Smithfield Street Bridge, freshly painting the railway trestles in the Strip District, and, of all things, purchasing pool chairs—$30,000 spent in total to reach every neighborhood, the first time the city had ever bought them—as if small, kept promises were a governing philosophy, which, for him, they are. “If you can do little things well, people trust you,” he said. Pittsburgh has already rebuilt the big things. What it’s testing now is whether trust scales the same way steel once did.
Pittsburgh is one of the cities in my forthcoming book, The Geography of Prosperity: A New Map of the American Dream, out from MIT Press in 2027.
The most pressing question facing leaders today isn’t what’s changing — it’s what to do about it. I help organizations answer that.




Japan has a similar story in Fukushima — but with vaccine factories instead of companies. The locals who stayed got jobs. The ones who left got nothing.