The World Series feels farther away than ever for the Yankees now. The last time they won it all was back in 2009, and for a while, there was still a living link to that championship on the roster. But that connection is finally gone, thanks to David Robertson.

Well, Robertson first showed up in pinstripes in 2008, a baby-faced rookie from Alabama who didn’t exactly look like someone built for the chaos of late-inning relief in New York. Still, he grew into the role and became a steady presence through some of the team’s most competitive years.

Now, with Robertson deciding to hang up his cleats, he’s walking away not just as a former Yankee, but as a piece of history!

“Veteran reliever David Robertson announces his retirement,” MLB insider Bob Nightengale shared via X.

So, with Robertson calling it a career, there are now no active major leaguers who can say they won a World Series with the Yankees. For the unversed, he spent his first seven seasons in pinstripes from 2008 to 2014. He was a key part of the bullpen during the 2009 championship run. After that, he moved on to the White Sox from 2015 to 2017, then made a brief return to New York before stops elsewhere.

However, statistically, Robertson’s peak came in 2011. That year, he put together a dominant season, logging 66⅔ innings with a microscopic 1.08 ERA. Now, at the end, he wraps up his career with a 2.93 ERA over just under 900 regular-season innings, along with nearly 1,200 strikeouts. For reference, since his debut, only Kenley Jansen has appeared in more games than Robertson’s 881. This says a lot about his durability and reliability in a role that’s usually anything but stable.

And beyond the numbers, his retirement leaves a real void in the Yankees’ clubhouse. There’s no one left who experienced the 2009 World Series title firsthand. So while Robertson stepping away is just another moment in the natural cycle of baseball, it also quietly underscores how long it’s been since the Yankees were last on top. And how distant that championship era now feels.

The Yankees have the best chance this year to revisit their golden era

The Yankees’ so-called golden era is usually pegged around 2011–12, when names like Derek Jeter and Alex Rodriguez still defined the team. Since then, dominance hasn’t exactly been their calling card. But here’s the twist: 2026 might be the year things finally flip!

Why? It starts with Aaron Judge. Heading into 2026, Judge is still very much the engine that drives this team, and he’s already being talked about as the favorite for AL MVP. If another 60-plus homer season with a slugging percentage pushing .700 is on the table, the Yankees are still riding the heart of Judge’s prime, a window that won’t stay open forever.

On top of that, the roster hasn’t changed much from last year. This is largely the same group that finished with the best record in the American League and made it to the ALDS. So, if they can build on that and take even a modest step forward, a World Series run suddenly doesn’t feel unrealistic.

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So while Robertson’s retirement makes the Yankees’ last championship feel further away than ever, it might also be setting the stage for a shift in the narrative. The past feels distant, but a turnaround could be closer than it looks.