Greatest Living Yankees: Ranking the Top 15 Old Timer Legends

Here are the top 15 greatest living New York Yankees…14 Old Timers plus one current superstar. 

#1 Derek Jeter (1995- 2014)

Derek Jeter, known better by many fans as ‘The Captain,’ has thoroughly established himself as the greatest living player to grace the pinstripes. When you think of Jeter, you think of championships and clutch moments. He was one of the catalysts for five World Series titles from 1996 to 2009, including a World Series MVP award in 2000 against the Mets, as well as 14 All-Star appearances and five Gold Glove awards.

#2 Mariano Rivera (1995-2013)

In the history of baseball, there is no more reliable arm to lock down the 9th inning of a game than Mariano Rivera. Rivera is universally known as the greatest closer of all time, shutting the door on opposing teams for 17 seasons in the Bronx. A five-time World Series champion, 13-time all-star, 1999 World Series MVP, and a staggering 0.70 career ERA in the postseason to go along with a 2.21 overall career ERA. As baseball’s all-time saves leader with 652, Mo is #2 among the greatest living Yankees in 2025.

#3 Aaron Judge (2016-Present)

It might seem premature to rank him this high on the list as a current player. However, some people still struggle to grasp exactly what Aaron Judge is doing fully. The two-time AL MVP is making a strong case for being the greatest right-handed hitter of this generation, receiving the Barry Bonds treatment from opposing pitchers in a time when steroids are more challenging to get away with. The only thing Judge needs to cement his legacy fully is that World Series ring.

#4 Reggie Jackson (1977-1981)

Known by many as ‘Mr. October,’ Reggie Jackson spent just five seasons in pinstripes, but the impact and role he played in helping them claim their 21st and 22nd World Series championships in 1977 and 1978 cannot be understated. His play in the 1977 World Series immortalized him in Yankee lore, as he hit six home runs for the series, including his famous three-home run game in Game 6, which clinched the series for New York.

#5 Bernie Williams (1991-2006)

When you hear about the Core Four of the late ’90s dynasty, Bernie Williams‘s name is left out when you mention Jeter, Rivera, Posada, and Pettitte. However, the argument can be made that the Yankees would not have achieved the same level of success without Bernie. Manning center field and anchoring the middle of the order for the better part of 16 seasons in the Bronx, Bernie was a five-time All-Star and the 1998 AL batting champion.

#6 Don Mattingly (1982-1995)

Don Mattingly‘s career in the Bronx is considered by many a disappointment, not due to any wrongdoing of his own, but rather the lack of team success surrounding him during his playing days. ‘Donnie Baseball’ was one of the best players in the sport throughout the 1980s and into the early 1990s, before he began suffering from chronic back issues. Despite just missing out on the late 90s glory years, Mattingly is still widely considered one of the greatest first basemen and captains the Yankees have ever had.

#7 Alex Rodriguez (2004-2016)

In the modern era, there might not be a player with a more confusing legacy with the Yankees than Alex Rodriguez. From the moment the Yankees and Texas Rangers agreed on the blockbuster trade in February of 2004, A-Rod brought constant noise along with him. Say what you want about his PED controversies, but there is no doubt he was one of the best players in the game during the first half of his tenure. When the 2009 playoffs arrived, A-Rod had established a reputation for playoff shortcomings, despite being a perennial All-Star. Still, he finally put that narrative to bed by slugging six home runs and 18 RBIs with a .365 average, helping the franchise win its 27th and most recent championship. 

#8 Ron Guidry (1975-1988)

‘Louisiana Lightning’ made an immediate impact on the Yankees’ pitching rotation from early on in his career. Ron Guidry was brought to the team at a time when the franchise was struggling and had recently undergone an ownership change. Guidry became extremely reliable from the moment he took the mound at Yankee Stadium and never looked back. He was the ace of the staff during their World Series wins in 1977 and 1978. His 1978 season is still considered one of the best single seasons by a starter in franchise history, boasting a record of 25-3, a 1.74 ERA, and 248 strikeouts.

#9 Jorge Posada (1995-2011)

Throughout the franchise’s 27 World Series championships, the catching position has always been a point of strength. From Bill Dickey to Yogi Berra to Elston Howard to Thurman Munson, Jorge Posada became the latest in a line of Yankees catching legends throughout his career. Posada was part of five World Series wins behind the plate, and his switch-hitting power made him a unique weapon in the batting order.

#10 Andy Pettitte (1995-2003, 2007-2010, 2012-2013)

Similar to Ron Guidry, Andy Pettitte established himself as a top-of-the-rotation arm from the minute he was called up in 1995. Pettite led the American League in wins in 1996 and helped anchor a pitching staff that won five championships in his tenure. In a must-win postseason scenario, there are not many guys more reliable than Andy Pettitte.

#11 Graig Nettles (1973-1983)

Graig Nettles was a catalyst for bringing the Yankees back to their winning ways when he joined in 1973. Nettles built a reputation as a guy nobody wanted to mess with over at third base. His toughness and all-star production helped catapult the team to winning back-to-back World Series in 1977 and 1978. Entering the 1982 season, Nettles earned the title of Captain, the team’s first since Thurman Munson’s tragic passing in August of 1979.

#12 Dave Winfield (1981-1988, 1990)

The 1980s were a confusing time for the Yankees. Despite leading the league in wins throughout the decade, they rarely saw the postseason after losing to the Dodgers in the 1981 Fall Classic. Dave Winfield signed a 10-year, $23 million contract with the team in 1981, making him the highest-paid player in MLB history at the time. Winfield made eight All-Star appearances with the Yankees from 1981 to 1988 while also winning five Gold Glove awards in right field.

#13 Goose Gossage (1978-1983)

The move to sign Goose Gossage in November of 1977 was met with questions at the time. The Yankees already had Sparky Lyle as the closer who just won the American League Cy Young Award the previous season. The move proved to work wonders, as the duo of Sparky and Goose essentially shortened each game for the opposing lineup. Gossage closed the final out of the 1978 World Series.

#14 Paul O’Neill (1993-2001)

‘The Warrior’ was acquired by the team before the 1993 season from the Cincinnati Reds, as manager Buck Showalter sought to instill a fresh culture within the team. Paul O’Neill brought discipline and accountability to the clubhouse, laying the foundation for one of the greatest dynasty runs in baseball history. O’Neill’s hitting prowess and steadiness in right field helped lead the team to its glory.

#15 Willie Randolph (1976-1988)

Perhaps one of the most underrated players in franchise history, Willie Randolph was a consistent presence for the Yankees at the top of the order for 13 seasons. As the man who hit No. 2 in the order and manned second base, Randolph was as steady as they come, helping anchor the team to their 1977 and 78 World Series victories.