This interview, which was condensed and edited for clarity, was conducted at the Hyatt Centric Times Square in New York City.
What did your parents do?
I grew up outside of Philadelphia. My father ran a landscaping business. My mom never worked outside the home, so she was the glue of our family. But I kind of lived a couple of different childhoods, because my father passed away when I was 13. My life hit an inflection point. My whole focus on school shifted after my dad passed away. I was the youngest of five kids, my dad had been the breadwinner, and I became hyper-focused on “How are we going to live and survive?”
What was your first job?
In the landscaping business, there are many different things you can do even as a kid — taking ivy cuttings and planting them in little peat pots to let them grow, digging trees, a lot of physical work. That’s what I would do for summers and on weekends from the time I was 10, or even younger. I was driving tractors and trucks when I was 13, 14 and 15 years old.
Is that legal?
No. In fact, when I was 15, the first time I ever drove a truck on the road there was an amazing blizzard. It was 1978, I’ll never forget it. It hit the whole East Coast. My brother had a contract to clear snow at this huge parking lot area, but he needed someone to drive one of the trucks over there to have it be available. He said, “Just get in the truck. I know you can drive it, because you’ve been driving around the nursery. Just follow me.” We get on the road, and there was so much snow, and I’m driving illegally at that time. The good news is, there was nobody else on the road.
How did you wind up joining the Pritzker organization?
A friend of mine was working with them, and I got a call from him. He said, “So we’ve decided that we’re going to probably hire someone of your experience level. Why don’t you come in and meet Jay?” I show up, and sitting at the table was Jay, the head of the machinist union at Eastern Airlines and his lawyer. Eastern was in bankruptcy, and so they were there pitching Jay on stepping in to take over the airline. At the end of that first meeting, Jay hands me the box of information they brought, and this was on a Tuesday. He said, “Why don’t you come back on Friday and tell me what you think we should do?” I didn’t know anything about airlines, and I knew even less about bankruptcy. That was my interview.