Oswaldo Cabrera is, by nature, a happy fellow, always smiling, always demonstrating genuine glee and good cheer. He has such a disarming “aww shucks” energy that it almost made his 2022 breakout somehow even more inconceivable. Where did this kid come from, and how is he doing this?

Even as Cabrera struggled in 2023, one asset above all helped the young Venezuelan maintain value: The guy can play literally anywhere. He hasn’t pitched yet as a pro, and he successfully fended off an effort by the team to convert him to catcher early in his Minor League career, when Cabrera was, in his own words, “a little bit *gordito.*” But across 159 big league games entering 2024, his appearances break down as follows: 76 games in right field, 60 in left, 18 at third base, nine at second, nine at shortstop, four at first base, three as a DH and one in center field. Truly, Aaron Boone can deploy the 25-year-old anywhere. That’s useful.

This, though, is a bit much.

It’s around lunchtime on a beach in Cozumel, Mexico, and Cabrera is standing in what we’ll call the outfield, although the fielding alignment could best be described as total chaos. The bases: actual coconuts. Cabrera is an active Major Leaguer, a real, live Yankee, but he’s something of a sideshow this afternoon as Ron Blomberg and Mickey Rivers -- two beloved former Yankees, the latter wearing a knit winter hat under a blazing Mexican sun -- piece together an ambitious Wiffle ball game. What starts as a couple people taking swings off Orlando Hernández (sans the famous leg kick, which he claims he can’t pull off anymore) has turned into dozens of beachgoers awaiting their own at-bats, trying to follow whatever rules Blomberg barks from his spot on the sand.

Cabrera, Blomberg, Rivers and “El Duque” are four of the attractions on the first Legends of Baseball Cruise. It’s an exclusive add-on package for a seven-night trip aboard the Celebrity Apex, where some 200 guests are on vacation with 10 members of the Yankees family. Also on board are Chris Chambliss, Cecil Fielder, Jeff Nelson and Graig Nettles, as well as baseball historian Marty Appel and the YES Network’s Michael Kay. The week features all the amenities of life on a luxury cruise ship, as well as Q&A sessions with the players, trivia contests and photo ops.

And one totally impromptu Wiffle ball game in Cozumel.

As selling points and ambassadors, it’s an attractive group, even if the word “legend” might seem something of a stretch. None of the players on board are in the Hall of Fame or Monument Park. In a way, though, that’s kind of the point. History can exist on the margins; indeed, every step on a big league field, to say nothing of a pennant-clinching walk-off homer or the first-ever at-bat by a designated hitter, is meaningful. Monument Park and the New York Yankees Museum teem with history, but neither purports to be definitive, to tell the entirety of Yankees lore.

“If you were a Yankee,” says Nettles, a two-time world champ, a former team captain and a master at simplifying things, “you were somebody.”

Cabrera is a Yankee in the present tense. Far from a legend on the level of some of his shipmates, he’s working to build his own pinstriped legacy. But as he learned aboard the Celebrity Apex last December, the rewards of joining the Yankees family will be part of his life forever, wherever this land-based journey of a baseball career leads him.

“Can you imagine how I feel,” Cabrera says, feet planted on a 1,000-foot-long, 130,000-ton megaship, but his eyes focused years into the future. “That’s the dream.”

***

Jeff Nelson remembers getting the call letting him know he had been traded to the Yankees while in Alaska for a Mariners promotional caravan. A Baltimore native, he had grown up rooting for the Orioles, then played in Seattle, where he helped depose the Yanks in the thrilling -- some might say heartbreaking -- 1995 American League Division Series.

Nelson loved pitching at Yankee Stadium, enjoying the regular mayhem taking place in the stands. But while he revered the game’s history and its presence in the Bronx, the scowling competitor had no love for the guys wearing pinstripes. “Even in the Minor Leagues!” he recalls during a day at sea. “I mean, I hated the guys in their Minor Leagues!”

Suddenly, he had to become a Yankee. Perhaps even more difficult would be liking the Yankees. “Well, you had to!” he says. “Now, you hated the Mariners and you hated the Orioles!” Putting on the pinstripes, though, helped him understand something about the team he had been conditioned to loathe.

“You could tell why they were hated,” he says. “They just had an attitude and an aura. It was a really big confidence in themselves, that they knew they could win.

“But once you put on the uniform, you knew that’s why they just carried themselves in a certain way.”

It really is about that uniform, the symbol of enduring greatness that dates back to a time even before the Yankees had won a thing.

It’s what Derek Jeter wore, barely at all changed from the days of Thurman Munson or Whitey Ford or Mickey Mantle. Joe DiMaggio wore pinstripes, as did Lou Gehrig and Babe Ruth.

“I think it all goes back to Babe Ruth,” says Appel, who has chronicled the history of the franchise in several books, including 2012’s Pinstripe Empire. “I think the players themselves want to wear the uniform that Babe Ruth made famous, and I think that draws them to the franchise. And, subliminally, it even draws fans to the franchise. ‘Oh, that’s the glamour franchise.’ That was Babe Ruth.”

When you play for the Yankees, you adopt their history. Things that happened generations ago become part of your past, extending beyond your own life span.

For a guy dressing in the uniform of the Nationals or the Padres, Babe Ruth is still the Sultan of Swat, the Great Bambino. His impact on the sport is as relevant as it would be anywhere else. But when you’re a Yankee? When Juan Soto plays his first home game this year, it will be in the same uniform that the Babe wore, likely at the same position on the field. It will be at the same Bronx intersection where Ruth became a sports deity. He’ll dress in a clubhouse with a large No. 3 hanging near the ceiling, and he’s free to spend some time roaming Monument Park, visiting the ghost of his most legendary predecessor.

“El Duque had limited exposure to baseball history and American culture,” Appel says of the Cuba native. “But he knew Babe Ruth and he knew Lou Gehrig and he knew DiMaggio and Mantle. And there was something special for him about putting on that uniform.”

If, like Blomberg, you grew up in the South in the days before the Braves moved out of Milwaukee or the Marlins and Rays even existed, the Yankees were the team you saw the most on TV, which is why a kid from Atlanta came of age revering Mickey Mantle. Closer to home, Michael Kay and John Sterling -- two of the most recognizable Yankees voices of recent vintage -- are as local as can be. Sterling grew up on Manhattan’s Upper East Side, while Kay is a Bronx kid through and through. “There were four male voices in my life,” Kay says. “My dad, Bill White, Frank Messer and Phil Rizzuto.”

As such, Kay and Sterling are more than familiar and well-prepared voices to guide viewers and listeners through nine innings. When something happens on the field, Kay says that he instinctively knows how to draw a connection to what came before. He lived the moments, and he remembers them. And, he points out, Sterling -- now 85 years old -- has even more institutional memory.

Kay thinks back to Aaron Judge’s chase for 62 home runs in 2022, and the pressure that he felt. The homer to establish a new American League single-season record would be replayed forever. The award-winning broadcaster didn’t want to step on the moment, to somehow get it wrong. It wasn’t his own legacy that he cared about, though. Kay didn’t want to do anything that could in any way ruin it for the player.

“A team’s broadcaster should have the team in their soul,” he says. “There are guys who do great jobs that go to other cities, and they immerse themselves in the history. But I lived Horace Clarke. I lived Jerry Kenney. I lived Gene Michael.

“It doesn’t mean you have to be a homer; it doesn’t mean you have to root for the team. But it means that you have to have them in your heart.”

***

Kay, like so many of the VIPs on the cruise, has lived multiple Yankees lives. He was a fan, a beat writer, and now he’s one of the team’s voices (although he shudders at being called “The Voice of the Yankees,” a title that he reserves exclusively for Mel Allen).

That evolution manifests in different ways for different people.

Aaron Boone authored one of the most famous moments in Yankees history when he walked off the Red Sox in Game 7 of the 2003 ALCS. At the time, as documented in photos and videos that seem to play on loop around the ballpark, he wore No. 19. But eagle-eyed Yankees fans will note that -- on days when he’s not dressed in some kind of windbreaker -- the current Yankees manager now wears the No. 17 that he had during most of his non-Yankees playing career (19 was taken by Masahiro Tanaka when Boone was hired in the Bronx).

On Old-Timers’ Day every year, though, Boone runs through the ceremony in his old No. 19, then changes to his present number for the subsequent Yankees game. Along the way, he lives both his past and his present. In his day-to-day life, every move is scrutinized; every minute played on a razor’s edge. Aaron Boone the old-timer, though, owns a perfect past, and a lifetime membership in a most special family.

“One of the great parts of this game is the bond and the closeness that you share with your teammates,” Boone says. “And when all the dust settles, those are the things you’ll look back on -- those relationships that you form with teammates, and those bonds that you share with teammates that last forever. … And those are the little reminders. With the stress and the grind of a long season, I guess one of the fruits of the game and one of the reasons you do it is for those relationships and that camaraderie of being a part of a team.”

Debbie Tymon, the Yankees’ senior vice president of marketing, is responsible for putting on the annual Old-Timers’ Day festivities, and she harks back to meetings with George Steinbrenner, when the Boss would personally go over the script and the plans for the day with her, making sure that the entirety of Yankees history was being celebrated. It wasn’t just about Hall of Famers or local legends. The idea was to try to convey as much of the team’s lore as possible in a single day, to express the ethos that “Once a Yankee, Always a Yankee.”

“Yankees fans are generational,” Tymon says, noting the importance of annual celebrations of great players, but also great moments -- be they Boone’s homer or Bucky Dent’s. There has to be -- and, thankfully, with more than 600 living alumni, there is -- something for everyone. “There are stories passed down from grandparent to father to son to grandson. Everybody within a family shares their great moment when they come to Yankee Stadium.”

Nelson always loved Old-Timers’ Day when he played. The pitcher remembers visiting Yankee Stadium with the Mariners and watching the festivities from the opposing dugout. When he joined the Yankees, he marveled at the way the returning heroes would share lockers with the current players on the day of the ceremony, all but forcing conversation in a clubhouse that wasn’t particularly roomy even on a normal afternoon.

All teams celebrate their histories. But Nelson, who currently calls games for both the Yankees and the Marlins, knows that it’s different in the Bronx.

“It’s a historical organization,” Nelson says. “The Yankees do such a great job of keeping everybody involved.

“If I was a Mariner,” he adds, pointing out the window toward Cuba in the distance, “this stuff isn’t happening.”

Old-Timers’ Day, to Nelson’s point, is a brief if celebrated blip on the calendar. For many of the guests, it’s a quick trip into and out of town. Which is why the former players on the December cruise around the Caribbean so relished having a full week together. From Blomberg and Rivers desperately dodging raindrops on a mad dash back to the ship to the seemingly endless meals, events and downtime together (all of which Blomberg consistently invited guests along for), it was an opportunity to dig deeper than the surface level, a Yankees fantasy camp at sea.

What was notable, though, was how the camaraderie on the ship spanned the generations. Nelson and Hernández and Fielder played together, but they spent the week listening to stories from Blomberg and Rivers, as well as Nettles and Chambliss. Cabrera, who wouldn’t be born for more than two decades after Chambliss’ pennant-winning homer, thrilled at the opportunity to listen, much as the ship’s old-timers enjoyed getting to better know a current player.

“He shows so much respect for us older guys,” Blomberg says. “And he’s such a nice kid.”

***

Oswaldo Cabrera has played less than a full season’s worth of games as a Yankee, and he enters the 2024 season staring at a roster filled with players that are pretty well locked into their positions. It’s great to have a guy that can play anywhere, and if he can’t crack a starting lineup, Cabrera is still a manager’s dream off the bench.

Still, though -- 159 games. In the course of a big league career, you hope that it’s just the beginning. Cecil Fielder didn’t even play 159 games with the Yankees; his New York career lasted just 151. He’s wearing a Detroit Tigers hat on his Baseball Reference page, his MLB.com profile page, even his Wikipedia page. But he was a Yankee. Even better, in 1996, he was a champion. “If you win,” he says,“ they’re never going to forget that.”

Cabrera actually left the ship early, before it returned to Fort Lauderdale, Florida. He didn’t feel like he could spend a full week away from batting cages and ballfields, not with so much work to do for the 2024 season. On the five days he spent on board, though, he learned so much about life, and about the future he can look forward to.

He posed for every picture with every fan, thanked them for their time, and had a blast on the beach in Cozumel (even before the Wiffle ball game). Whenever Cabrera retires, wherever he goes, whatever he does, he’ll always have this.

“That’s the inspiration for me,” Cabrera says. “When I see all those superstar guys from the past, and they are here, and you see how the people show the love for all those players, for me, it’s an inspiration to say in my mind, ‘I have to get better. I have to stay with the Yankees for a lot of years. And I want to be in this position at some time in my life.’”

The thing is, he’s already most of the way there. Oswaldo Cabrera is a Yankee. Whatever comes next won’t change that. At last year’s Old-Timers’ Day, Tymon and her staff welcomed almost the entire 1998 team back to Yankee Stadium. It didn’t matter that Mike Figga and Todd Erdos don’t exactly have the name recognition of Derek Jeter and Mariano Rivera. They were all invited because they were all Yankees.

Nelson, who pitched for that ’98 team, was there, too. He has been around baseball enough to know that some things are the same everywhere and others are different. Yankees fans expect to win every night and will let their own players hear it in bad times -- something, he notes, Cardinals fans would never do.

But even if there aren’t moral victories in a New York baseball season, a former Yankee’s life is filled with the greatest of participation trophies. You were one of us once. You’re one of us forever. It means something when that “one of us” makes you a Yankee. “It’s a fraternity that you want to belong to,” Chambliss says. “It’s a very distinguished group.”

“I’ve met many, many players over the years who all have expressed the same thing,” Appel says. “I’d give three years of my career if I could have played one year for the Yankees, for all that it would mean in my life and my post-baseball career and my personal standing. I’m a former Major Leaguer, but I’m not a former New York Yankee. It’s a difference.”

We think of legends in terms of sports heroism, but consider the word itself. A legend is just a story that’s passed down, often embellished. When old-timers get together, wherever it may be, there’s plenty of that. They can keep sharing the same stories, Blomberg says, because “they’re not the truth. When you get older, your home runs that went 450 feet go 500 feet and then 550. And nobody knows the difference!”

And that’s a fitting coda to the first Legends of Baseball Cruise, which is scheduled to sail again this coming December. Your mileage may vary on some of the names and the feats and the Q ratings, but that’s almost entirely beside the point. It’s the passing of a torch -- from father to son, or grandmother to granddaughter, or from Mickey Rivers to Oswaldo Cabrera -- that crystallizes the idea of the Yankees family, one that is owned, and carefully honed, by all who are part of it.

Jon Schwartz is the deputy editor of Yankees Magazine. This story appears in the Spring 2024 edition. Get more articles like this delivered to your doorstep by purchasing a subscription to Yankees Magazine at www.yankees.com/publications.