A few minutes before 1 p.m. on a perfect 60-degree day in late autumn, Ken Singleton is on his way to his favorite Italian restaurant. Located in the heart of Baltimore’s famed Little Italy — a well-known destination for the city’s greatest athletes, dignitaries and celebrities — Sabatino’s is not yet bustling.

As Singleton, 74, makes the two-block walk from his car and approaches the three-story building, he crosses paths with no one. The barren streets of Little Italy, which before the COVID-19 pandemic would normally have been packed on such a picturesque Friday afternoon, are undoubtedly a sign of the times.

Singleton, wearing a light purple sweater, green pants and a leather jacket, makes his way into the decades-old restaurant on Fawn Street and is greeted by the maître d’.

“How are you guys doing?” he asks the woman. “Are you getting through this thing OK?”

Singleton’s tone is sincere, his eyes filled with concern. With a shrug and a half-smile, the hostess turns to lead Singleton through the restaurant’s barroom and into a dining area. He sits down in his customary corner booth situated in front of a window. The thin silk blinds merely blur the bright sun; the room is still naturally illuminated.

Moments later, Vince Culotta, the longtime owner of the restaurant, stops by. He has known Singleton for years, not because the newly retired YES Network analyst enjoyed his finest days on the baseball diamond with the Baltimore Orioles, but because the former ballplayer’s wife of more than 30 years, Suzanne, serves as the promotions director for Charm City’s iconic Little Italy.

The outpouring of concern that Singleton shares with Culotta is heartwarming. When the waiter comes to the table, Singleton shows him the same respect and kindness. For anyone lucky enough to have worked with Singleton during his 24-year run broadcasting Yankees games, first for MSG Network and then for the YES Network, none of these anecdotes would seem out of the ordinary. That’s how Singleton treats everyone; it’s who he has always been.

“That came from my parents,” says Singleton, who resides in a suburb of Baltimore. “I will always remember one of the first games my dad came to after I got to the big leagues with the Mets. It was Father’s Day at Shea Stadium, and my dad came to the game with 10 of his coworkers from the post office he worked at across the street from Madison Square Garden. One of the guys called me over and said, ‘Your dad is very proud of you. But if you turn out to be half the guy he is, you’re going to be something special.’ It was nice to hear someone who my dad worked with say something so nice about him. I just always felt that it’s nice to be important, but it’s more important to be nice to people. They pay it back, or at least most of them do. If you are nice to people, you are usually going to get that respect back.”

When the waiter returns, Singleton orders his second-favorite dish on the menu, clams casino, for an appetizer. He doesn’t need any extra time to decide on an entree.

“The lasagna here is as good as you’ll find anywhere,” he says before ordering the signature dish as a main course, adding — with a level of positive analysis familiar to Yankees fans — that the dish deserves awards.

From growing up some 15 miles north of Manhattan, in Mount Vernon, N.Y., through his playing career with the Mets, Montreal Expos and Baltimore Orioles, and then over the course of a 37-year broadcasting career, Singleton earned the respect of others at every stop along the way. His colleagues with the YES Network hoped that he would stay in the booth forever, but at the end of the 2021 season, during the fourth inning of the Yankees’ Oct. 2 game at Yankee Stadium, Singleton asked play-by-play man Michael Kay for the floor and proceeded to announce that 2021 would be his final season in baseball, the sport he began playing when he was 4. The following day, the Yankees celebrated Singleton’s career in a pregame ceremony during which he tossed a ceremonial first pitch.

“I pretty much knew at the end of this past season that it was time,” he says softly from the quiet restaurant’s booth. “For one, the pandemic made it much less enjoyable to be a broadcaster. Not being able to travel and instead doing road games from home took something away. I loved traveling; it was a big part of the experience of being a broadcaster.

“It was also time for me to have the chance to be with my family whenever I want. Even though I wasn’t doing a lot of games in recent years, I still felt compelled to watch every Yankees pregame show and every game. To me, baseball is an everyday sport, whether you’re a player or a broadcaster. Things change from day to day. When people would ask me why I felt tied down even though I wasn’t doing that many games, I would explain that I had to watch everything. I had to know who was doing what in order to put together a good broadcast when it was my turn. I was either going to be all in or all out.”

Singleton’s “all in” broadcasting career began mere months after his playing career came to a close in 1984. Toronto broadcaster Tony Kubek approached Singleton about announcing select Blue Jays games on television. Singleton took him up on the offer, as long as the former Yankees shortstop was willing to show him the ropes during his first spring in the booth. With the same dedication that he brought to the field, Singleton found early success behind the mic. What followed was a long tenure broadcasting both Blue Jays and Expos games for The Sports Network in Canada.

“I was doing about 60 Montreal games and 20 Toronto Blue Jays games for the Network when Expos execs asked me to do all of their games,” Singleton says as a large dish of clams casino and some bread arrive at the table. “So from that point, I was doing every Expos game that was televised, and for the ones that weren’t on TV, I was doing the radio broadcast.”

The promotion gave Singleton his first crack at doing play-by-play, and the value in that experience was not lost on him.

“That was important, because players retire every year, and I realize that some of them may be more popular than me,” Singleton says. “That means that if they get hired to be color commentators, I could be out of a job. But not everyone can do play-by-play. So, I started doing it, and that was one thing that I had going for me that other former players didn’t. It certainly helped pave the way to a long career and to me coming to New York.”

Despite those credentials and league-wide respect, the Yankees gig was not a shoo-in for Singleton after he auditioned with MSG executives in 1996.

“That winter, [fellow player turned broadcaster] Jim Kaat and I came to New York to do a voice-over of the World Series for MSG,” Singleton says. “The executive producer and president of MSG both told me that I had the job, but that I had to meet George Steinbrenner before anything could be made official. I thought that the fact that I had never played for the Yankees would be a sticking point. Not many teams had broadcasters who played for other teams but not with their club at all. George brought me in and said, ‘You did a lot of bad things against us,’ but that was really a compliment. I thought, ‘Well, I was just trying to do my job.’ But George knew that I was from New York. He probably knew that I could pronounce the names of all of the towns around New York City, like Ronkonkoma and Mamaroneck. Years later, I found out that he had actually tried to trade for me when I was a player, and it all started to make sense. He always treated me well, even on the days when he wasn’t that happy about what the team was doing.”

From the start of Singleton’s quarter-century in the Yankees’ booth, the team on the field made his job especially exciting and filled the experience with joy.

“It was awesome working with a team like that because you feel that every night, you’re going to win,” Singleton says. “Even if they lose, there’s not going to be much of a losing streak. I like bringing good news to people. As far as being associated with a team like that, you feel as though you’re part of something that is very special. I felt like we had a chance to win the whole thing every season I was broadcasting for the Yankees. What happens to you as a broadcaster is that the fans start to see you in that light as well — as a winner.

“The Yankees are trying to win the whole thing every year. When you’ve won 27 times and no other team has won more than 11, you’re playing against yourself and your own record and your history as much as you’re playing against every other team. The people who are watching you have been told stories from their parents and their grandparents about how good Mickey Mantle was or how good Yogi Berra was. So now, you’re going to have a chance to tell people how good Derek Jeter was or Aaron Judge is. This is going to be your legacy as a Yankees fan. You want to be able to do the same things that your parents or grandparents did for you. That’s what being a Yankees fan is all about.”

Every season has been special for Singleton, but none more than 1998, when the Yankees posted an almost unimaginable 125-50 record (including the postseason) en route to sweeping the San Diego Padres in the World Series.

“I felt like the weatherman in San Diego,” Singleton says, now with a delicious-looking plate of lasagna in front of him. “You knew that it was going to be very good every day. Even if you had a cloudy day every once in a while, you knew it was going to burn off and the sun was coming back. It was fun covering that team. They were good, and they knew that they were good. They knew that if they got the ball into Mariano Rivera’s hands, people in the Stadium could start looking for the car keys.”

As Singleton digs into the main course, Culotta comes back to the table with a glass of red wine.

“This is on the house,” the owner explains. “You’ll always be one of our favorites, and we feel the same way about Suzanne.”

As always, Singleton remains gracious, volleying back compliments and gratitude, before returning to the topic at hand, “the best baseball team in history.”

How much of a sure thing did that World Series championship feel like? Singleton remembers a brief chat with another legend of the sports world in which the announcer found himself subconsciously leaning into the coronation’s inevitability.

“We had already won the first two games in New York and the first game in California,” Singleton says. “I was walking through the tunnel by the Yankees clubhouse, and I saw Fred Couples, one of my favorite golfers. He came up to me and said, ‘Ken Singleton, I really like you on TV.’ Then, he said, ‘I have a problem. I have a chance to go out of town to do an outing in a few days and make a lot of money, but I also have tickets to Game 5 of the World Series. I’m not sure what to do. I said, ‘Give those tickets to someone you don’t like and move forward with your plans to go out of town. You’re going to see Mariano Rivera close out this World Series in Game 4 tomorrow night.’ That’s exactly what happened, and when I saw Fred a few years later, he reminded me of that story.”

As awe-inspiring as that season was, Singleton’s two favorite games as a broadcaster came in the years that followed. Only one of those memories is a result of the action on the field.

“My favorite game was when Jason Giambi hit the grand slam in May of 2002 to win the game in extra innings, after Minnesota had scored three runs in the top of that [14th] inning,” he says. “Jim Kaat and I were doing the game, and he had done a few extra-innings play-by-play calls before that, so he asked me to do that one. I can still remember how excited the crowd was when that ball got into the seats.”

Another night that stands out in his mind came as a result of an issue related to Singleton’s would-be broadcast partner.

“A close second was a game here in Baltimore that I was supposed to do with Paul O’Neill,” Singleton says. “But he had some trouble getting on his flight, and I ended up having to do the game by myself for the only time. The game was tied going into the ninth inning, but luckily Jorge Posada hit a home run. Before the ball landed, I looked out into the bullpen to see if Mariano was warming up, and, of course, he was. The Yankees won, and I went down to the clubhouse to thank both Jorge and Mariano. If that game had kept going, I think my voice would have been gone. So, for one night, I got to be Vin Scully and do the game by myself. It wasn’t easy. You have to know your sport in order to do that; you have to know how to follow the field.”

Although Singleton acknowledges the challenge associated with doing a game by himself, he was steadfast in mastering the craft of broadcasting Major League games. He left no stone unturned in his pursuit of constantly putting together compelling broadcasts.

“As long as I had my health and I did my homework — and by that, I mean watching the Yankees and the teams they would be playing in my next broadcast — I knew that I could be a good broadcaster,” he says. “When I would get to the visiting ballpark, I would find the broadcasters for that team and ask them what was going on with their club. If you make one original point during the game, as opposed to throwing out a whole bunch of statistics that you get from the game notes, people will remember it. For example, if you talk about a player from the other team who is not running hard to first base and you found out from that team’s broadcaster that he has a sore hamstring, it will change the fans’ perspective on that player. Instead of thinking that the player just doesn’t want to hustle, they’ll realize that he was told not to run hard in order to stay on the field for future games.”

Besides the pride Singleton has in the way his hard work paid off, being part of the YES Network’s climb to the top of the list among all regional sports networks is close to his heart.

“Working for the YES Network, it doesn’t get any better than that for a broadcaster,” he says. “Everyone there is elite. People from all over the world know the YES Network. I’m very proud to have been a part of it right from the beginning and to have seen it grow.”

Long before he was part of the YES Network’s rise, Singleton was an integral part of the Baltimore Orioles’ resurgence that began in the mid 1970s and crested in the ’80s. When Singleton was dealt from Montreal to Baltimore in December 1974, his career was about to take off, and the Orioles seemed poised to reclaim the dominance they had displayed over the previous decade. When he got the news, Singleton had already contemplated how the trade would affect his baseball life.

“The night before I got traded, Mike Torrez and I were out late in Montreal,” Singleton says. “We found out that the Orioles had made a trade for Lee May. They were already a good team, and they were really stocking up. After I got home, my phone rang at 6 in the morning, and it was Mike. He told me that he got traded to the Orioles, and I said, ‘That’s great. We were just talking about what a good team they have. I’m going to miss you.’ He said, ‘No, you’re not. You’re coming with me. Hang up, because your phone is going to be ringing in a little while.’ Sure enough, [Expos general manager] Jim Fanning gave me the news. I was happy, because the Orioles were a much better team than the club we had in Montreal.”

After hitting .285 with 46 home runs over his three seasons north of the border, the 28-year-old Singleton batted .300 in his first season in Baltimore. Two years later, he hit .328 with 24 home runs, finishing third in the 1977 American League MVP voting. For the New York City native, the most memorable moment that year happened at Yankee Stadium.

“Although I wasn’t voted into the 1977 All-Star Game as a starter, I really hoped I would get picked by the American League manager, Billy Martin,” he says. “I hadn’t been an All-Star yet in my career, and I knew that my parents would be able to be at the game because it was in the Bronx. We were playing the Yankees about 10 days before the game in Baltimore. When we finished taking batting practice, I was walking back to our clubhouse, and Billy came up to me and said, ‘I’m taking you with me to the All-Star Game.’ I ran into the clubhouse and called my dad to tell him.”

Following the Midsummer Classic — in which Singleton played three uneventful innings in right field and was hit by a pitch from Rick Reuschel in his lone plate appearance — the Orioles, Yankees and Red Sox duked it out, with the Yankees winning the American League and ultimately the World Series. Despite falling short in ’77, Singleton’s Orioles, led by Earl Weaver, weren’t going away. Among the memories that Singleton has of playing for the Hall of Fame manager, few endure as much as what happened on the final day of the Orioles’ season.

“We had a big rivalry with the Yankees in those years,” Singleton says. “In 1977, after the Yankees had clinched, Earl got in front of us and pulled out a telegram that was supposedly from Billy Martin that read, ‘Thanks for a good race. See you all next year.’ Earl ripped it up in front of us, and using language that only he could, he said, ‘We’re going to get those [expletives].’ I don’t even know if the telegram was real, but it gave us something to think about over the winter.”

Weaver ran a tight ship in Charm City, but Singleton credits him — and the collection of all-time great players that he teamed with — for the glory days he experienced in orange and black for a decade.

“I got off to a really bad start one season,” Singleton recalls while sipping a cup of decaf coffee. “Earl dropped me to eighth in the lineup, when my average dipped to around .185. He called me into his office and asked, ‘When are you going to start hitting?’ I said, ‘I don’t know, I’m trying.’ He asked me if I was sick. I told him that I wasn’t. He then asked me if I was tired, and I told him that I wasn’t. Then, he looked me in the eye and said, ‘Well, I’m sick and tired of you not hitting.’ It still took me a little while to get going, but I hit .330 during the second half of the year, and I went 2-for-3 in the last game, which allowed me to lead the team in hitting.”

The Orioles didn’t “get” the Yankees in 1978, but they did get past them a season later, capturing Baltimore’s first AL pennant since winning three straight from 1969 to ’71. During the ’79 regular season, Singleton clubbed a career-high 35 home runs, batted .295 and was runner-up for the AL MVP Award.

“Beating out the Yankees and Red Sox was something in and of itself,” Singleton says. “They were both great teams with a lot of [future] Hall of Famers. The hardest thing about losing the ’79 World Series was that we were up, 3 games to 1. I know exactly why we lost: We got overconfident. We came back to win Game 4, and we thought it was over, but Willie Stargell wouldn’t let the Pirates lose. I was really down after we lost, but a few weeks later I was reminded of how special it was to play in Baltimore. I was walking down the street, and a guy came over to me simply to say, ‘Thank you for the effort. You had a good year, and you guys are going to get back.’ To me, that’s what the Orioles fans were all about.”

The Orioles did get back to the Fall Classic in Singleton’s penultimate season as a player, defeating the Philadelphia Phillies, 4 games to 1, in the 1983 World Series. At 36 years old, the veteran outfielder — who played in 151 games that year and hit .276 — finally realized his dream of winning it all.

“In that World Series, we went up 3 games to 1 again,” Singleton says. “But this time around, nobody said a word. We knew that 1983 was our last shot to win the whole thing because we were all getting older. From that standpoint, when we did it, it was even more exhilarating. Having to wait so long made it even sweeter. From 1979 to ’83, we had 15 of the same players on the team. That’s very rare, but we were able to do that because we were all good players. We just couldn’t put it all together until 1983.”

Singleton came back for one more season, but he struggled in 1984. When that season concluded, he knew it was time to hang up his spikes, and he did so with no regrets.

As the father of four finishes off the cup of decaf, he prepares to head back to his small Maryland town, but not before reflecting on the years he spent in Baltimore one last time.

“It was great,” says Singleton, who finished his 15-year Major League career with a .282 average and 246 home runs. “Playing on three All-Star teams and in two World Series, that’s pretty special. The fans here were very much behind the Orioles. We won 100 games in back-to-back seasons. We won more games during my 10 years here than any other team in baseball. I’m still close to a lot of the guys I played with here in Baltimore, and when you continue to spend time with the guys you won with, it keeps you thinking about how special the things you accomplished were.”

Singleton’s career in the bigs began close to where he grew up in New York. He became a star in Baltimore, then returned to the Big Apple many years later as an announcer. To that point, Yankees fans — and George Steinbrenner — only knew him as a rival. Still, that didn’t prevent Singleton from endearing himself to the Bronx faithful as well as The Boss.

In hindsight, that should come as no surprise. When you’re good at your job and you’re as genuine, good natured and simply as kind as Singleton is, it’s easy to be loved anywhere life takes you.

Alfred Santasiere III is the editor-in-chief of Yankees Magazine. This story appears in the April 2022 edition. Get more articles like this delivered to your doorstep by purchasing a subscription to Yankees Magazine at www.yankees.com/publications.