Cape Cod League Stories: Derek Falvey, Minnesota Twins

Derek Falvey speaking at the SABR 52 Convention in Minneapolis in 2024. (Photo: Jacob Pomrenke)

 

The Cape Cod League helped inspire his love of baseball as a kid. It then provided a launching pad that took him to the heights. Derek Falvey was named executive VP and chief baseball officer by the Minnesota Twins in 2016, then promoted to president of baseball operations by the Twins in 2019, as of November 2024 adding responsibility for the business side of the organization to his portfolio as well.

Born in the Boston area in 1983, Derek developed an interest in baseball as a young boy. He grew up in Lynn, Massachusetts. His father, Steve, worked in construction, as a piledriver, notably working for 15 years on “The Big Dig” that began in 1991 and rerouted Boston’s Central Artery highway through a lengthy underground route beneath the city. The Ted Williams Tunnel connects the I-90 highway to the airport under Boston Harbor, and Steve Falvey worked on that as well.

Derek’s uncle Jake Falvey was the longtime head coach for Everett High School, just north of Boston. He had done some umpiring, as a college umpire and in the minor leagues. Starting in 1988, when Derek was 5, Jake Falvey began umpiring Cape Cod Baseball League games in the summertime. He put in 13 seasons, from 1988 to 2000.

Derek recalls, “I went down there often in the mid- to late ’90s with him. This is going back to when I was 11, 12. We’d drive down early enough to beat all traffic. We’d maybe hit a beach for a little bit, for an hour, grab a bite to eat, and then go over to one of the games that he did. He’d be working the game, and I’d watch from the stands.

“I loved baseball. I played it. I have a huge passion for it. My parents loved the game, too. I grew up playing it in Lynn, but my uncle Jake was probably one of the most significant influences for me when it comes to the game. He and I talked baseball all the time. He came to any of my high school games that he could when he wasn’t coaching. I remember going down to the Cape with him and seeing some of the best players come through.”1

Derek went to Trinity College, and pitched on the college team, the Bantams (“not particularly well, and I got banged up along the way.”) But he had really enjoyed those excursions to the Cape, and enjoyed taking part in games himself from Little League through college. With his playing career coming to an end, graduating in 2005 with a degree in economics, he started thinking about what would come next.

“I said to myself, I like writing up players, I think I have an amateur eye for scouting. I’ve been watching baseball for a long time. I want to learn about scouting. I realize that I know very little, but I want to learn as much as I can about scouting in addition to maybe putting myself out there a little bit.

“I decided, I’ll do this for the summer and see what happens.”

That was the summer of 2007. He just started doing it on Cape Cod – on his own, with no sponsorship, no position of any kind, not even as a volunteer or intern.

He took a notebook and a handheld camcorder, and began to shoot video of the players and write up his own appraisals of those players – his own scouting reports, creating individual DVDs per player. At the time, there was not a lot of amateur video available. YouTube and other such outlets were in their infancy when it came to amateur video clips. Derek would then hand the DVDs to pro scouts who were at the Cape League games.

“These guys got to have jobs to do. You want to be respectful. If they’ve got their radar guns up, you don’t want to be asking a bunch of questions. I kind of just tried to fit in.

 

 

“I had my own camcorder, my notebook. I was writing my stuff down. Usually between innings, it was kind of natural for a scout to ask, ‘Who’re you with?’ I’d give a little spiel about what I was trying to do. ‘Oh, interesting. Good luck.’”

Most of the scouts were on the Cape for a week or so, from other parts of the country. He approached them and said, essentially, “I’m not working for any team. I’m trying to learn about scouting. I’m trying to break into the industry if I can. If you’ve got any feedback for me or any ideas, I’d love it. When you’re home, if you need any more video, I’m happy to send more. I’ll keep it confidential.”

He agreed, “Some scouts probably looked at me a little sideways.” Overall, though, reflecting the spirit one immediately senses in Cape League baseball, he said, “But a lot of them – the vast majority of them – were super-gracious and super-willing to chat with me. They’d give me some tips and feedback about what I was writing up. Before they left, a few of them asked me questions about getting new video or how’s this guy going, or what do you see about this guy. … It was really fun to develop some of those relationships and those friendships through the summer.

“I wrote up a ton of players, cut up a ton of video. My hope was that at the end of the summer, someone somewhere would pass my name up to their boss when they were going through the hiring process. And that’s essentially what happened.

“I was really fortunate to have my stuff passed along.”

Early on, he struck up a friendship with Brent Urcheck, a New England/East Coast area scout for the Cleveland Indians. “I think he took a liking to the work I was doing and just passed it up to Brad Grant, who was the scouting director in Cleveland at the time. He sent it along to their director of baseball operations, Mike Chernoff, who was handling hiring. I don’t think that would have happened if we didn’t develop that friendship standing behind the fence there and exchanging a few ideas.

“There were a few other guys who did that for me too. I was very fortunate. At the end of that summer, I had three or four teams reach out with different types of positions to interview for. I wasn’t sure I was going to get any of them.”

When the summer season ended, Derek got a couple of calls from teams that interviewed him for area scout positions – one was to cover Louisiana/Alabama/Mississippi, another was for North Texas and Oklahoma. He interviewed with the regional cross-checkers and supervisors and the scouting director. But the call that paid off came from Mike Chernoff of Cleveland. They flew him out to interview for an internship in their baseball operations department. A few days later, he was offered the position. He accepted, and moved to Cleveland, where he worked out of Progressive Field.

“It was just a tremendous opportunity to do a little bit of scouting, work across baseball operations, help the scouts with their work. A good bit of my focus was on prepping for the 2008 draft. Helping scouts with some video and organizing our information for the draft.”

Clearly, he had talent and he had drive. With the franchise – now the Cleveland Guardians – he worked his way up to become director of baseball operations by 2011 and then assistant general manager in 2016, before being hired by the Twins later that year as executive vice president, chief baseball officer.

And in due course, president of baseball operations for the Minnesota Twins. And, in a very real way, it all started on the fields of Cotuit and Bourne in the Cape Cod Baseball League when a driven and talented youngster decided to try to work his way into professional baseball.

At the end of January 2026, a shift in Twins ownership led to a mutual agreement to part ways, with Falvey leaving the organization to pursue other opportunities in Major League Baseball.2

BILL NOWLIN was born in Boston and lives in Cambridge, Massachusetts. He sometimes says he “hasn’t gone far in life.” He hesitates to admit it but, despite going to well over 1,000 games at Fenway Park (including every game in 2022), and hearing about the Cape League for years and years, he had never been to a game on the Cape. He’d even been to the Midnight Sun Game in Alaska and seen baseball in several other countries. That changed once this book got underway. Now he gets it!

 

NOTES

1 Author interview with Derek Falvey on January 13, 2025.

2 Dave Campbell, Associated Press, “Twins executive Derek Falvey departs in mutual agreement as organizational revamp continues,” APSports, January 30, 2026. https://apnews.com/article/twins-derek-falvey-7245d331dd0025d248cb9e4de49e2e76