Veteran MLB reliever David Robertson announced his retirement Friday, ending an 18-year career that spanned eight different teams.
Nine of those years were spent with the New York Yankees, who selected him in the 17th round of the 2006 MLB draft. He reached the majors two years later and won his only World Series ring the following season with the Yankees’ 2009 championship team.
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Robertson is the only active player left from the 2009 team, which creates quite a historical fact as we enter the 2026 season.
Without Robertson reaching the major leagues, MLB would not have a single active player win a World Series ring with the Yankees. How rare is this? There has been only one such MLB season since the Yankees first won the World Series in 1922, a span of 104 years.
That season was 1995. Now 2026 will join the season, and possibly 2027 and 2028, and so on.
David Roberts spent the first seven years of his career with the Yankees before returning in 2017 and 2018. (Photo by Rich Schultz/Getty Images)
(Rich Schultz via Getty Images)
You don’t need a baseball historian to tell you that the Yankees won the World Series regularly from the 1920s to the early 1960s. Apparently, MLB had players with Yankees World Series rings during that time. Most of them are still playing for the Yankees due to reserve clauses.
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In the history of the Yankees, the team has experienced three famous World Series droughts: from 1962 to 1977, from 1978 to 1996, and from 2009 to the present. To find a player whose career spanned the first drought, you could look to Al Downing, who got some cushy jobs with the Yankees in 1961 and 1962 but stayed in MLB until retiring in 1977 with the Los Angeles Dodgers.
The closest player to that feat from 1978 to 1996 was Hall of Famer Rich “Goose” Gossage, an All-Star with the 1978 Yankees who played until 1994, his age-42 season. He did spend one season away from Major League Baseball (MLB) in 1990 while playing for the Fukuoka Daiei Hawks in Japan, but the void was filled by former teammate Willie Randolph and others, who stayed with the team until 1992.
There was a mini-drought from 2000 to 2009, apparently hosted by guys like Derek Jeter, Jorge Posada, Andy Pettite, and then this one.
To be clear, this is just a fun little fact. The Yankees aren’t panicking about David Robertson retiring. Still, it highlights how far the Yankees have strayed from their history over the past few decades.
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The club had a chance to break the drought in 2024, but instead ran into the Dodgers, who have now usurped Major League Baseball’s Big Bad status. With each year that doesn’t bring a new batch of players with Yankee rings, the pressure will continue to mount.
