The New York Yankees have not won a World Series since 2009, and ever since, the quest for the Commissioner’s Trophy has continued for captain Aaron Judge and his team. This year, after repeatedly talking about winning the World Series throughout the offseason, the Yankees appear to have a legitimate chance to make a deep postseason run. So how can they get there? According to this Yankees legend, the answer lies in what Brian Cashman and the front office need to do next.

“The window is closing, and it puts tremendous pressure on Brian Cashman, ownership, the fanbase,” Alex Rodriguez said on WFAN Sports Radio when discussing the Yankees’ next World Series. “What an absolute tragedy it would be to have one of the greatest of our generation only go to one World Series and not win.”

A-Rod was part of the Yankees team that gave the franchise its last World Series title in 2009. Since then, a drought has followed, and fans have grown tired of waiting. The Yankees legend believes that if Judge, currently 34, retires without winning a World Series ring, it would be no less than a tragedy.

Judge has contributed massively to the game as well as to the pinstripes. He has set extraordinary standards over his decade-long career, as he is a three-time AL MVP, going back-to-back for the last two years. Despite being on the IL, he was selected for his eighth All-Star team this season. However, the only gap in his resume is a World Series. He was close to winning one with Juan Soto on his team back in 2024, when the offensive duo lit the AL on fire.

For now, the Yankees (54-42) hold the leading Wild Card spot in the AL. However, it’s the Tampa Bay Rays that lead the AL East as well as the American League.

Yet A-Rod believes that, despite Judge’s injury, the Yankees have the best chance of making it to the World Series this year.

“This is the weakest the American League has been in all our lifetimes; the National League is very strong,” A-Rod observed. “You have a scenario where you can play the White Sox and the Rays and go to the World Series.”

After highlighting the above facts, A-Rod demanded that Brian Cashman and the management go all in and strengthen the Yankees’ roster. Cashman needs to fill the deficits with the Aug. 3 trade deadline on the horizon, especially since Aaron Judge is still on the IL.

As the Yankees begin the second half of the season, Judge has undergone re-imaging during the All-Star break after sustaining the injury in late April but has yet to receive a positive update. His progress has not been sufficient for him to resume baseball activities, and he has not played since May 31. Initially, it was expected that he would be out for four to six weeks at most because of his fractured right rib, but several analysts now believe he is unlikely to return until September, and that’s a bitter reality the Yankees have to keep in mind now.

MLB.com’s Bryan Hoch quoted Judge, saying, “Some progress, some healing going on, but not fully healed. So we’re still waiting on one more doctor to take a look at it, kind of see how we progress forward the next couple weeks.”

While Judge’s chances of returning during the regular season appear slim, given that his rehab has been limited to lower-body workouts and neck exercises, with no upper-body or overhead lifting, the Yankees will need to be firing on all cylinders if he is to make an impact in October.