Former Yanks on transition from player to exec

April 13th, 2020

The interview with Kevin Reese, Matt Daley and Dan Giese for this story and podcast took place during Spring Training, before camps were closed due to the coronavirus pandemic.

As front offices have been filled with Ivy League types and analytics whizzes in recent years, the number of former players moving into executive roles has seemingly dwindled.

The Yankees have their share of number-crunchers, but Brian Cashman’s front office includes a host of execs with playing experience, giving the general manager plenty of points of view to consider in his decision-making process.

Three of those men -- Kevin Reese, Matt Daley and Dan Giese -- didn’t just play in the Majors; they all wore pinstripes during Cashman’s tenure in the GM chair. Now, they’re helping shape the organization’s future.

“Having played here, just about every player has conversations about, ‘If we got to make some of these decisions, we would do it different,’” said Reese, the club’s senior director of player development. “We had those conversations as players sitting in our hotel room. It’s kind of cool; these guys in this room, we all had these talks and here we are helping to kind of steer some of these guys’ careers. It’s pretty exciting. There’s never a dull moment around here.”

For the first time in its four-season run, the Executive Access podcast features a roundtable conversation in its latest episode, as Reese, Daley and Giese discuss their playing careers, their move to front-office life and more.

Daley and Giese, the Yankees’ two directors of pro scouting, believe that their experience as players has been beneficial to them in the second phase of their baseball careers.

“On the scouting side, building that Rolodex of players, it gives you a jump start,” Daley said. “I played for 10 years, so I got to see a lot of really good players. I knew what the good players looked like and I got to see players who maybe we thought were going to be better than what they ended up being. You can kind of figure out why they didn’t get to their ceiling that their talent had.”

Giese posted a 2.86 ERA in 396 games over parts of 12 seasons in the Minors and a 4.22 ERA in 35 Major League appearances, getting first-hand experience when it came to the difficulty of making that leap. That experience has been valuable as he assesses players both within the Yankees' organization and on the rosters of the other 29 clubs.

“Realizing how difficult it is to make it to the Major Leagues; seeing a guy’s stuff, if you don’t have the big stuff you better have elite command and control,” Giese said. “I’m always playing with, ‘If this guy is going to make it, he’s going to have to make up for this bad area over here,’ You have a good sense that a Triple-A All-Star doesn’t always translate into a good Major League career, because it’s a huge, huge gap from Triple-A to the big leagues. I have a good sense of what that takes.”

Reese points out that while their respective experiences as players can help them relate to today’s players, he has to “check myself a lot, because my situation is so much different” than many of the youngsters within the farm system.

“We’ve got guys from all over the world, from different economic backgrounds,” Reese said. “You try to put yourself in their shoes … When you’re talking to a player and you can say, ‘Look, man, I’ve been in your shoes to some extent. I want to try to talk through some of the things I know bothered me at that point.’ It’s being honest with players, trying to help them understand how we see them.”

Although the trio combined to play in just 159 games, they have some not-so-secret weapons at their disposal inside the organization. Other former Yankees -- players such as Andy Pettitte, Hideki Matsui and Nick Swisher -- have remained with the club in special advisor roles, giving Cashman and his front office the ability to deploy the former All-Stars when and where they’re needed.

“Let’s be honest; we can have the greatest coach in the world telling you, ‘Here’s how I think you should do it,’” Reese said. “But if Andy Pettitte walks in and starts talking about how to make a cutter move, everybody is going to stop what they’re doing and listen. It’s huge.”

Might some of these players consider more prominent front office roles for themselves in the future? Where these roles were once ambassador-type jobs, retired players such as Pettitte, Swisher and Matsui have been more involved in recent years.

“Their willingness to sit in on pro scouting meetings, to sit in on player development-objective type of meetings, to sit on with Cash and understand what’s going on in the state of the front office has been great,” Reese said. “In the past, guys would just sort of pop around and say, ‘Hey, I’m so and so; remember all the home runs I hit?’ There’s been a lot of involvement in meetings and a true understanding of what we’re trying to do. That takes it to another level.”

Listen to the entire interview on Executive Access, available on Apple Podcasts, Spotify, Google Play, Art 19 or wherever you get your podcasts.