Yankees Magazine: From On Field to On Air

Some former big leaguers find a second calling in the Yankees’ broadcast booth

April 6th, 2019

John Flaherty figured he was being diligent when he showed up at work with a binder stuffed with notes.

There was no such thing as too much preparation during his 14 seasons as a big league catcher. Pitchers’ meetings, hitters’ meetings, scouting reports, signs -- he had to know everything when he was behind the plate. And so, he had spent hours meticulously crafting this file, loading it with stats and anecdotes and different talking points that he wanted to touch on while calling his first game.

He was proud of the work he had put in and what he had compiled. This was a different job, though, one Flaherty didn’t know all that much about. He already had some pregame studio experience, but there was no training or audition. Flaherty had never done this before. The cheat sheet -- or sheets, rather -- would surely come in handy while he adjusted to the booth. At least that’s what he thought until his play-by-play partner, Jim Kaat, stopped him dead in his tracks.

“He said, ‘John, you and I are at a bar, having a beer, watching a baseball game, and we’re just gonna talk baseball,’” Flaherty says, recalling his debut as a color commentator in 2006. “‘All that stuff that you prepared is great, but the last thing you want is to have to force that into a telecast. If that research is important enough, you’re gonna remember it.’”

Flaherty had only done the same thing he had his entire playing career, but Kaat was the seasoned veteran on the mic. So, Flaherty obliged.

Fast forward years later, and Flaherty is just one of several former Yankees thriving in their second careers as broadcasters for the YES Network. When it comes to ex-players turned on-air personalities, the YES Network’s baseball broadcasts have as much depth as any team in baseball. In addition to Flaherty, there’s David Cone, Paul O’Neill and former Orioles outfielder Ken Singleton. The quartet has more than six decades of MLB experience, though it takes more than just a lengthy playing career to make it on live TV.


John Filippelli, a.k.a. Flip, is in charge of acquiring talent at YES. The network’s president of production and programming is always looking for prospective broadcasters, paying close attention to players during their careers. He observes their news conferences and tries to meet as many of them as he can. He wants to see how they answer questions, relay information about the game and relate to fans.

“I look for someone who’s open-minded, somebody who’s insightful, someone who has passion and love for the game,” Filippelli explains. “You can find parts of that, but if you find all of that together, you’ll find yourself a really great announcer.”

Michael Kay, the longtime Yankees play-by-play man on YES, adds that an understanding of the media’s purpose and a sense of humor are always helpful as well.

Broadcasting affords former players the opportunity to stick around baseball after they hang up the spikes. Flaherty said he started thinking about the possibility at the urging of his agent in 2003, when he joined the Yankees. O’Neill just wanted to continue being around the team after he retired prior to the 2002 season. Singleton, who never played for the Yankees but spent 10 of his 15 seasons in the American League East, had the chance to start his broadcasting career while still active, filling in on sportscasts for a Baltimore television station during the 1981 strike. Cone joined YES in 2002 before -- to the dismay of George Steinbrenner -- attempting a comeback with the Mets in 2003. He didn’t return to YES or broadcasting until 2008.

“I kind of jokingly say this -- but only half-jokingly -- there was a little bit of a probationary period when I left the Yankees booth to go play for the Mets,” Cone says. “It took me a little while to kind of work my way back into the Yankees universe.”

Players have to do something once that itch to play goes away for good. Coaching is the most natural choice. But broadcasting isn’t far behind.

“These players made a lot of money,” Filippelli says. “When they retire, there are very few jobs that are going to pay them as much as they made as players. So, they have to make an adjustment in their minds that this is about doing something constructive; that they enjoy staying close to the game. We give them a chance to stay close to the game, to extend the brand of who they are.”

A play-by-play man such as Kay, studio host like Bob Lorenz or sideline reporter such as Meredith Marakovits went through years of schooling and training to become a broadcaster, but the former players are tossed into the fire when they become analysts and color commentators. Filippelli is confident the knowledge and personality will come out naturally. He can teach them the ins and outs of presentation and delivery as they go.

“That was probably the best thing about it. I don’t know if I would have wanted to put in the time and effort training to talk about a game I played my entire life,” O’Neill says. “Were there mistakes made early? I’m sure. Are there still mistakes? I’m sure. I’m not a professional at broadcasting. I didn’t take this in school. I played baseball.”

“I really didn’t know what I was doing,” Singleton adds, recalling his early days with WJZ-TV, “but the producer was good.”

Of course, any new job comes with adjustments. While every former player knows the game, they’re learning about the world of live television on the fly. Little things, such as knowing which camera to look at or when to talk, are all somewhat foreign. Eliminating everyday crutches such as “umm” and “like” takes practice. Enunciation has to be clear, and energy is essential -- even when the game is entering the 15th inning at 2 a.m.

No different from on the field, the bright lights of a studio or the red “On Air” signal can get the blood pumping. And the more live reps the better.

“The nerve-wracking part was just the sense of timing and rhythm,” Cone says. “When to talk, when to back off and let the play-by-play guy kind of lead the way. Just getting a sense of how to use the content that you have from your playing career. Most ex-players have tremendous content, but it’s more about how to use that content, how to deliver it.”

There’s also the personal matter of going from being a teammate in the clubhouse to a member of the media. Ex-players that enter broadcasting know the players and coaches on the field, often well. That means sometimes having to criticize a close friend.

Flaherty remembers watching Jorge Posada struggle toward the tail end of his career. The two backstops were close teammates, but there was no covering for Posada’s trajectory. The best way to handle the awkwardness is to explain why someone is underachieving, rather than pile on the negativity.

“You know you’re in the toughest media market in New York,” Flaherty says. “You know you have to tell these Yankees fans what’s really going on because they’re so intelligent. You have to acknowledge what’s going on, which is extremely difficult when you’re friendly with somebody.”


A lot of networks try to keep their units small. There’s an argument to be made for continuity; give fans a chance to really bond with the broadcasters throughout the course of a season (or several decades). Create a sense of familiarity. There’s this old idea that viewers are inviting broadcasters into their home when they turn on the television, and it’s easier getting to know a smaller group.

Filippelli doesn’t see it that way, though. One thing he appreciates about the YES Network’s roster is the variation; the ability to mix and match different combinations. More personalities mean viewers can get an assortment of backgrounds, approaches and perspectives.

Cone, the only pitcher of the bunch, has become an analytics savant while simultaneously adding comic relief to the telecast. O’Neill, goofy in his own way, offers the insight of a feared (and hyper-emotional) hitter. Flaherty brings a catcher’s mindset to any situation. Then there’s Singleton -- the elder statesman of the group -- who is still providing new stories from his lengthy career as he prepares for his final season.

“It’s like you have five friends, and all these friends bring you different things,” Filippelli says. “You like some for the same reasons, some for different reasons, but you have the variety of those five really good friends and they all interact with each other and they like each other. Guess what? It’s going to be a very nice party.”

That’s another important element: No matter the combination, everyone seems to genuinely get along in the booth. That’s essential not only to the workplace, but also to the viewer.

“You’re almost a salesman for the game,” Kay says. “If you want people to tune in and spend three hours with you, you better sound like you’re having a good time.”

Not only does the network’s talent have a good time together, but everyone seems to enjoy the sport that they’re watching. That’s not always the case with former players turned broadcasters. There are a few who like to play the Back In My Day card, fighting back the tide of an ever-changing game that now relies heavily on analytics, shifts, bullpen usage and other new-era adaptations. Some ex-players often sound like they’d rather be watching anything else -- and that can get old quickly.

Rarely do fans direct those complaints at the YES Network, however, whose lineup has embraced the game’s modernization.

“I have no problem with a difference of opinion,” Cone says. “Sometimes, you hear some ex-players that want to criticize the modern game or analytics, and they don’t really understand the analytics part of it. It’s sort of like saying, ‘Hey, I didn’t like that movie,’ or ‘I didn’t like that book.’ Then you ask them, ‘Did you see the movie? Did you read the book?’ And they say, ‘Well, no, but I don’t like it.’ That’s my big pet peeve. At least educate yourself before you’re going to trash a whole sector of the game that’s become so important.”

Cone, especially, has become skilled not only in his use of analytics, but also in his ability to make them easily understandable to his audience. He was introduced to advanced metrics first as a player. His agent, ahead of his time, used sabermetrics to help Cone win a few arbitration cases against the Mets in the early 1990s. The Cy Young Award winner soon realized there was more to a stat line than just wins and losses.

Now, every Major League front office has come to the same conclusion. Analytics drive baseball’s decision-making every step of the way. To dismiss their existence is to dismiss crucial information for the viewer -- even if not everyone wants to hear it.

“You’d be doing your broadcast a disservice to ignore it,” Kay says. “It’s not only a big part of the game, it is the game right now. It’s how they make decisions. But the one minefield that you have when you’re doing this is that you have to make it readily understandable. In a quick phrase, what’s WHIP? What’s FIP? Stuff like that. David’s pretty good at that. But you have to realize that a lot of your audience might be older, and they don’t want to hear it, so you have to serve two masters.”

To Kay’s point, a broadcast can’t just be all about numbers. There needs to be a mixture of stats, analysis, anecdotes and, sometimes, just plain old fun. It’s not unusual for the YES booth to get a little silly here and there. Jokes and pop culture references run the gamut. So do the personalities.

It’s that blend that keeps fans coming back night after night during the marathon that is a 162-game season. YES has been the most-watched regional sports network for 14 of the last 16 years, so Filippelli’s formula must be working.

The ex-players seem to love everything about the job, and it’s easy to understand why. In a lot of ways, broadcasting is just like playing. There are teammates, different roles, preparation and practice, pressure to perform and, of course, a whole lot of baseball. If that’s all you’ve ever done your entire life, it’s the perfect fit for your next act.

“It’s the second-best job to playing,” Singleton says. “There’s nothing better than playing, but of course, you get older and you graduate. I’ve enjoyed every minute of it.”

Lookout! After delaying retirement, 2019 will (probably) be Ken Singleton's final season in the booth

After 12 years of broadcasting Montreal Expos games, Ken Singleton was ready to interview for a new job. MSG Network had been courting the Mount Vernon, New York, native to call Yankees games in time for the 1997 season, but the former Mets, Expos and Orioles outfielder required The Boss’s approval before he could hop in the booth at Yankee Stadium. George Steinbrenner had the final say over such matters -- and a sharp memory for the damage Singleton had done during his 15-year playing career.

“Our fans aren’t going to like you,” Steinbrenner, seated at the end of a long table in a Legends Field conference room, sternly told Singleton. “I can recall all the bad things you did against us.”

A career .282 hitter against the Yankees, Singleton was prepared with the perfect response. “Well Mr. Steinbrenner, with all due respect, I was just doing my job.”

“You did it very well,” Steinbrenner shot back. “You and that Eddie Murray guy.”

The truth was that Steinbrenner had long considered Singleton one of his favorite opposing players. Singleton said the late owner had tried to pry him loose from the Orioles more than once, but Baltimore never budged. Steinbrenner even knew Singleton’s uncle, who worked with children’s services in New York and often arranged trips to Yankees games. Despite some unpleasant memories on the field, the decision to hire Singleton was an easy one for Steinbrenner.

Singleton has been calling Yankees games ever since. The 2019 season will be his 23rd doing so, his 35th overall as a broadcaster and his 18th with the YES Network. It will be his final campaign before he retires -- at least that’s his stance right now.

The 2018 season was supposed to be it for Singleton, but the veteran play-by-play man and color commentator reconsidered after an outpouring of fan support and an irresistible offer from John Filippelli, the YES Network’s president of production and programming. The plan is for Singleton to call just 25 games in 2019 after doing 55 a year ago. He will do two series in his current hometown of Baltimore, two series in Florida -- his preferred retirement destination -- against the Rays and one or two series at Yankee Stadium. He will also get to choose a road series or two that he wants to travel for.

“It’s kind of easing my way out, so to speak,” Singleton says. “Mr. Filippelli was very persuasive. He tried to make it as easy as possible for me. It was almost like I couldn’t say no to that.”

The softer slate will allow Singleton to visit his family more. His grandkids live in New Jersey and are already getting their feet wet in the sports world. His 9-year-old grandson plays both baseball and football, though it’s no secret which sport Singleton would rather he focus on. Filippelli, meanwhile, is hoping he can change Singleton’s mind again once he has some time to adjust to his new work-home balance.

“Around the All-Star break, I’ll start to wear him down,” Filippelli says, laughing but serious. “I’m nothing if not dedicated. I will try really hard to get him to stay a little longer.

“YES is not the same place without him. We really want him back. He’s part of what we do. He’s in the wallpaper in the booth.”

Asked if he’s 100 percent sure about retirement this time, Singleton answers with confidence before leaving the door open just a crack. He has made his intentions clear, yet acknowledges that he’s already had one change of heart.

“Umm, yeah,” he says of his plan to call it a career after 2019. “Unless I really like this schedule.

“It’s nice to know that people enjoy what you do and enjoy it over a number of years. It’s nice to know that there’s quite a few people who didn’t want me to stop. It’s very flattering, but all things have to come to an end some time.”