10 stars on the hunt for first World Series ring

Many of our greatest baseball players never won a World Series. Ted Williams never won one. Neither did Ken Griffey Jr., Ty Cobb, Tony Gwynn, Barry Bonds, Harmon Killebrew or Ernie Banks. (Heck, while we’re here, Mike Trout hasn’t won a postseason game, much less a championship.)

This is not quite as big a deal in baseball as it is in other sports. For Hall of Famers such as Dan Marino, Karl Malone, Randy Moss, Patrick Ewing and Charles Barkley, never winning a title will be part of their biographies forever. But not winning a World Series isn’t the first thing that comes to mind when you think of Bonds or Williams. It’s a very different sport.

Still, you’d like to see the all-time greats get a World Series title. Half the fun of the Dodgers’ championship in 2020 revolved around Clayton Kershaw adding that final line to his Cooperstown résumé. These are some of the greatest players we’ve ever seen, and it just feels right for them to win a title before they retire.

Today we look at 10 active players who have had the best, most storied careers but have yet to win a World Series … and have a chance to do so this year. Some of these guys are sure-fire Hall of Famers, some are still trying to build a case and some aren’t particularly close but have been among the game’s best for years. This could be their year.

Gerrit Cole, SP, Yankees
Has appeared in 7 postseasons (1 World Series)

The year after he finally won his first Cy Young Award, Cole has taken a step backwards in 2024, both in health (15 starts) and effectiveness (3.97 ERA, his highest since 2017). He’s still one of the last starting pitchers any team wants to face in a postseason series. He signed with the Yankees for three main reasons: 1) That big contract; 2) It was the team he cheered for as a kid; 3) To have the best chance to win a World Series. He can still help make that happen in 2024.

Bryce Harper, 1B, Phillies
Has appeared in 6 postseasons (1 World Series)

A World Series ring remains the only thing Harper doesn’t have at this point. The Nationals, rather famously, won one the year after Harper left. The Phillies then reached the World Series in 2022 and came just short of making it again last year. The first postseason series Harper played in, the 2012 NLDS against the Cardinals, began when Harper was only 19 years old. His next postseason game will be his 50th. He’s responsible for some all-time playoff moments. He’s gotta get a ring eventually … right?

Aaron Judge, OF, Yankees
Has appeared in 6 postseasons (0 World Series)

Fun fact about Judge in the postseason: He’s only hitting .211 in 44 games, with a meager (for him) .462 slugging percentage. In his most recent postseason series, the 2022 ALCS against the Astros, he went 1-for-16. He also might be having the best season, ever, for a right-handed hitter. To cap it off with his first World Series appearance, for the franchise that he in many ways has personally rejuvenated, would be a fitting way to finish such a historic year.

Thanks in part to some slow starts, Lindor hasn’t made an All-Star Game since 2019, even though he’s about to finish in the top 10 of MVP voting for the third straight year. (And this time, he looks primed to finish at least second in the NL.) He’s having the best year of his career for a team that has been one of the best second-half stories in baseball, and he’s the unquestioned team leader. It feels like he hasn’t quite elevated himself to the top-shelf status reserved for inner-sanctum New York superstars. Winning a World Series for the Mets would very much do it.

Manny Machado, 3B, Padres
Has appeared in 5 postseasons (1 World Series)

It’s been a down year for Machado by his standards, but he’s starting to look a lot more like himself now that he’s healthier. (Though many with the Padres believe he won’t truly be healthy until 2025.) Machado made his first postseason appearance in 2012 with the Orioles at age 20, and he lost his lone World Series appearance, with the Dodgers, back in 2018. He has a bit more work to do to lock down his Hall of Fame status, and winning a World Series would do a lot of heavy lifting.

Well, he’s finally going to play in his first postseason game this year, so that’s a start. (Might he even pitch in the postseason? Apparently, we can’t rule it out.) Ohtani is one of those all-time talents who belongs on the largest stage possible, and he is of course with the Dodgers in large part to get them their first World Series in a full season since 1988. (Though 2020 still counts!) He has many years ahead of him to take bites of the apple, and you have to think he’ll get a ring eventually. But there’s no time like the present.

José Ramírez, 3B, Guardians
Has appeared in 5 postseasons (1 World Series)

The forever-underappreciated superstar from Cleveland – he should have won the 2020 AL MVP Award over José Abreu – has been outstanding year after year for a decade now. But he never gets the love he deserves. (I’m a longtime proponent of coming up with a catchy nickname for him. That would help.) You know what else would get him that love and attention? Winning a World Series for Cleveland. That would end MLB’s longest active title drought. They’d build a statue of him. They might build several.

J.T. Realmuto, C, Phillies
Has appeared in 2 postseasons (1 World Series)

We’ll see how Hall of Fame voting turns out for Buster Posey and Yadier Molina in the next few years, because it’ll give us a sense of how it may turn out for the best catchers of a more recent era: the Royals’ Salvador Perez (who already has a ring) and Realmuto. While Realmuto remains an undeniable leader on his team, the thing that Perez (and Posey, and Molina) has that he doesn’t, that title, is the thing that Realmuto may have his best chance to get this year.

Carlos Santana, 1B, Twins
Has appeared in 6 postseasons (1 World Series)

Santana, rather famously, came this close to winning a World Series with Cleveland in 2016. Winning one this year in Minnesota would be a fitting capper to a 15-year MLB career that has always flown a little bit below the radar. The Twins will be the fourth team Santana has represented in the postseason in the last five seasons, as he was with Cleveland in 2020, the Mariners in 2022 and the Brewers last year. Three of MLB’s top four active players in career games – Andrew McCutchen (first), Santana (second) and Paul Goldschmidt (fourth) – have never won a ring. But Santana is the one with a real shot to change that this October.

He’s probably going to end up with at least 500 homers in his career – he’s signed with the Yankees through 2027 – and will be the center of an absolutely fascinating Hall of Fame discussion someday. Winning a World Series with the Yankees will be a helpful data point in his favor … and almost make his contract look worth it by itself. He’s put up big postseason numbers, too, with a .635 slugging percentage and 11 homers in 27 career playoff games, all for the Bronx Bombers.