Veteran reliever David Robertson’s retirement creates uncomfortable fact for the Yankees

Veteran MLB reliever David Robertson announced his retirement Friday, ending a playing career that saw him appear with eight different teams over the course of 18 years.

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, in his second season, won his only World Series ring with the Yankees’ 2009 champion team.

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Robertson was the only active player remaining from that 2009 team, and that creates quite the historical fact as we head into the 2026 season.

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With no Robertson in the majors, there will not be a single active player in MLB who has won a World Series ring with the Yankees. How rare is that? It’s been true for only one other MLB season since the Yankees’ first World Series title in 1922, a span of 104 years.

That season is 1995. And now 2026 is set to join it, as well as potentially 2027, and 2028, and so on.

You don’t need a baseball historian to tell you the Yankees regularly won the World Series from the 1920s to the early 1960s. Obviously, MLB had players with Yankees World Series rings throughout that time. Most of them were still playing for the Yankees, thanks to the reserve clause.

Over the course of Yankees history, the team has had three notable World Series droughts: from 1962 to 1977, from 1978 to 1996 and 2009 to present. To find a player whose career spanned the first drought, you can look up Al Downing, who received light work with the 1961 and 1962 Yankees but lasted in MLB until his retirement with the Los Angeles Dodgers in 1977.

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For 1978 to 1996, the closest any player comes is Hall of Famer Rich “Goose” Gossage, who was an All-Star on the 1978 Yankees and kept playing until 1994, his age-42 season. He did spend a season out of MLB in 1990 while playing for Japan’s Fukuoka Daiei Hawks, but that gap is covered by former teammate Willie Randolph, who played until 1992, and assorted others.

There was the mini-drought from 2000 to 2009, obviously covered by Derek Jeter, Jorge Posada, Andy Pettite and more, and then this one.

To be clear, this is just a fun little fact. The Yankees are not panicking because David Robertson retired. Still, it underscores how far the Yankees have drifted from their history over the past couple decades.

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The club had a chance to break the drought in 2024, but ran into a Dodgers team that has now usurped its status as MLB’s Big Bad. The pressure is going to keep building with every year that passes without a new set of players with Yankees rings.