#309: Ben Zobrist, 2x World Series Champion – Prepare for pressure
How Leaders Lead with David Novak
September 17, 2026
Game 7 of the 2016 World Series had gone to extra innings. The Cubs were trying to break a 108-year championship drought that some called a curse. If you’re a baseball fan, you already know what happened next: With two runners on base, Ben Zobrist stepped up to the plate.
Speakers David Novak, Ben Zobrist
TopicsManagementBusinessEntrepreneurship
David Novak (0:00)
Hello, and welcome to another episode of How Leaders Lead with David Novak. Today's guest is Ben Zobrist. He's a three-time All-Star, two-time World Series Champion, World Series MVP, and arguably one of the greatest utility players in baseball. And the timing for this conversation could not be better, as baseball heads into the postseason. We're coming up on the 10-year anniversary of one of the most iconic moments in baseball history. It was game seven of the 2016 World Series, and the Cubs hadn't won a championship in 108 years.
Ben comes to the plate in extra innings and delivered the go-ahead hit that helped make him World Series MVP and a legend in Chicago.
As you'll hear today, though, the greatest pressure in Ben's life actually came after he achieved his biggest dream. In today's episode, you're going to learn how to prepare for the moments in your life when everything is on the line, and why leaders everywhere need to prepare themselves for success just as seriously as they prepare themselves for failure. Enjoy today's conversation with David and Ben, and I will see you at the end of the episode for the debrief.
David Novak (1:13)
You know, as I understand it, your manager for the Cubs, Joe Madden, had a dress code. And he said that if you think you look hot, wear it.
What's the best outfit you ever showed up to the ballpark in?
Ben Zobrist (1:27)
Oh, man, there were some rough ones there occasionally. But yeah, he had lots of different themed trips.
I think that the one that sticks out is the pajama trip, just because you get to be comfortable, you know, real comfortable. If we had a long trip from one side of the country to the other, it's like, hey, let's just lounge around and treat it like you're at home on the couch, which was, you know, that was really a welcome relief when you're traveling as much as we were.
David Novak (1:56)
I bet, you know, it's the 10-year anniversary of your World Series win with the Cubs, which broke as, you know, broke that 108-year curse of the Cubs. Now, 10 years later, looking back, what do you appreciate about that accomplishment, that accomplishment today that maybe you couldn't appreciate back then?
Ben Zobrist (2:16)
Yeah, well, I think when you're going through it, your focus is so much on exactly what you have to do to be successful, right? And once we get, we've gotten away from it for 10 years now.
And I'm away from the game. I've been retired for a number of years. You really can start to look at it and try to appreciate and celebrate some of it a little bit more. And then I've also been able to see the impact that it had on fans, the impact that it's had on my own life, but fans and a lot of people that I've connected with over the years, right? So, you know, it's really the reason why I get a chance to speak, probably the reason why I had a chance to write a book here, because of what we accomplished on the field. But when you're going through it, you got to really focus on the details of accomplishing the mission at hand, right? So now I get a chance to really reap the rewards of that.
David Novak (3:06)
And you were the hero of that World Series. And so let's go back to game seven. You know, I hate to do this to you because I know you told the story a zillion times, but I'm going to do it anyway.
You come to the plate, next innings, there's two runners on.
David Novak (3:23)
Cubs will take the lead.
David Novak (3:25)
Al Mourad digging to the plate.
David Novak (3:28)
Zobrist delivers seven to six in the ten.
David Novak (3:45)
You make the big hit. What's the part of the story, though, that leaders really need to understand?
When you think about leadership, what do you think is the insight there in terms of what happened?
Ben Zobrist (3:59)
Here's the thing. You said that I was one of the heroes of that World Series. And when you're in the company of people that are great, it's hard not to focus on trying to be great. But the really great thing about that is when you trust the people around you, all you really have to focus on is what you have to do.
So the nice thing about being a part of that team was I didn't feel like I had to carry the weight. I didn't feel like I needed to do anything special or be a leader, you know. And so really I think leadership in that moment for me was how am I leading myself?
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