It’s one of my favorite times of the year. The buzz starts to build as we put the finishing touches on our annual "Executives to Watch" list. It’s always exciting to spotlight the sharp, ambitious people who are taking on bigger roles and shaping the future of our industry. This year, we’ve got 11 incredible professionals who are absolutely ones to keep an eye on.
But you know, as I was looking over the new list for 2026, I couldn't help but think about the leaders who paved the way. To really appreciate where we're going, I think it's so important to remember where we've been and who got us here.
And that brings me to one person in particular: the late, great Kevin Kelley.
A Leader Forged in Fire
I had the privilege of interviewing many of the industry's heavy hitters over the years, but my conversations with Kevin always stuck with me. He passed away this past summer, and the news hit a lot of us hard.
I won’t pretend we were close friends, but as a journalist, you get a pretty good sense of a person. And Kevin Kelley was the real deal. He spoke with this incredible directness—no fluff, no jargon—just a wealth of knowledge that made every conversation feel substantial. You always walked away smarter.
To get a sense of who he was, you have to go back to 1987. AIG made him the CEO of Lexington, their massive Excess and Surplus company. He was just 36 years old. Think about that for a second. The sheer weight of that responsibility on someone so young is hard to imagine.
But Kevin wasn't just anyone. He was part of this legendary group of executives who came up under the one and only Hank Greenberg at AIG. We’re talking about people like Brian Duperreault, the late Dinos Iordanou (who we also sadly lost in June 2024), and Hank’s own son, Evan Greenberg. These guys were all brilliant, driven, and somehow thrived under the immense pressure of working for a boss who was famous for demanding nothing short of excellence.
I once asked Kevin what those days were like. He told me, “All I know is that every day they seemed to be throwing more at you. I guess Greenberg saw how you responded and if you liked it he just gave you more.”
It’s no surprise that every single one of those guys went on to lead enormous insurance operations. Evan Greenberg is at the helm of Chubb, Iordanou built Arch into a powerhouse, and Duperreault famously turned around both Marsh and AIG. They were forged in a crucible, and they came out stronger for it.
Straight-Shooting Wisdom I'll Never Forget
Putting together the "Executives to Watch" list each year is a big project, and I used to call on guys like Kevin and Brian Duperreault for their insights. I wanted to know who they thought was the real deal.
I’ll never forget one year I called Kevin and asked him what the field of candidates looked like for the coming year. Without missing a beat, he replied with his classic bluntness, “Slim pickins, Dan.”
That was Kevin. No sugarcoating, just his honest take.
I also remember asking him a question that was on everyone’s mind for years. I asked if he thought AIG would have survived the 2007-2008 financial crisis if Hank Greenberg hadn’t been forced out in 2005.
His response was immediate and certain. “There is no doubt in my mind,” he said. There was no hesitation, just absolute conviction. It’s hard to fathom the sense of loss people like Kevin, who poured their lives into building that company, must have felt watching it crumble.
He also shared some wisdom on risk that has always stayed with me. He said, “In my opinion, picking the right businesses and building the right businesses are probably just as important as scale.” In an industry that can get obsessed with being the biggest, it was a powerful reminder that being the smartest is what really matters.
Looking Forward, With Gratitude for the Past
It was a shock to hear that Kevin, a man who ran marathons, had passed away just six years into his retirement. He was truly one of the great ones, and so were his teammates from those formative AIG years.
So as we turn our attention to the impressive 2026 class of Executives to Watch, let’s take a moment. Let’s remember the giants like Kevin Kelley. The leaders who weren't afraid of pressure, who spoke with candor, and who understood that true success isn't just about size—it's about substance.
The next generation has some mighty big shoes to fill, and that’s a legacy worth celebrating.
