The Kiddush Cup: A Labor Day Tradition in Stamford

Labor Day always feels bittersweet. It’s the unofficial end of summer, the start of the school year for our kids and grandkids, a time for one last beach trip or backyard barbecue with friends.

But here in Stamford, CT, Labor Day also means something else: the annual Kiddush Cup softball game. Every year, Congregation Agudath Sholom and the Young Israel of Stamford take to the field for a friendly showdown to see which shul gets bragging rights—and the chance to house the shiny Kiddush Cup trophy—for the next twelve months.

This year marked the 27th consecutive game between the two shuls. Not even COVID-19 could stop this tradition from carrying on. The first game was played back in 1999. After the two teams split the first six matchups, Agudath Sholom began to take control, especially between 2014 and 2020, when they strung together seven straight victories. Overall, Agudath Sholom leads the series 18–9.

The winning team gets to proudly display the trophy in its shul until next year’s game. The base of the cup is engraved with every winner since the beginning of the annual event, making it a living piece of Stamford Jewish history.

When the first game was scheduled, I faced a personal dilemma: which team should I play for? Sharon and I are full active members of both shuls, and my loyalty was evenly split. My solution? I volunteered to be the umpire! In theory, I was the perfect neutral party. In practice … well, let’s just say it didn’t take long before I realized that making close calls was a quick way to lose friends on both sides. Thankfully, Larry Miller, a professional umpire who happened to be part of the community, stepped in after a few years and handled the job far better than I ever did.

Although it’s mostly males who play in this annual softball game, occasionally a female athlete will participate – and they are more than welcome to play.  One year Hannah Lastoff pitched a complete game for the Young Israel squad, leading the team to a victory.

Over the years, the Kiddush Cup has had its share of funny moments. One year, Agudath Sholom won the game, but the shul couldn’t find the trophy—it turned out it was still sitting at the engraving shop!

Another time, Rabbi Daniel Cohen, spiritual leader at Congregation Agudath Sholom, posed for a picture holding the cup while Agudath Sholom had a big lead … only for Young Israel to come back and win the game. Ever since, Agudath Sholom has had a new rule: no one touches the trophy until the last out is made!

One year Rabbi Adam Miller, then the shul rabbi for the Young Israel of Stamford, played in the game.  He came up to bat, hit a ground ball to the infield, and started running to first.  His kipah fell off, and he ran back to retrieve it.  No one remembers if he was out or safe at first!

Despite the natural rivalry between the shuls, the games have always been played in good spirits. Friendships across teams are common, and with Stamford’s Jewish community growing so rapidly, both shuls have thrived. These days, many families belong to both synagogues. In fact, I once watched dual members show up on game day, check whether Agudath Sholom already had a full roster, and then happily switch sides to play for Young Israel.

Simeon Wohlberg, who has been a fixture on the Agudath Sholom team since the very beginning, reflected on how meaningful this tradition has been. “When this game started 26 years ago, there was no collaboration between the two shuls. This was the first time we really had come together. Now, our community is united in so many ways—joint programs, dual memberships, friendships across shuls. I’d like to think our little softball game helped pave the way.”

Seth Linzer, who has been a player-manager for the Young Israel since the Kiddush Cup began, reflected on his own longevity.  “I have missed only one game, and that was because of a kidney stone that I got on that morning. I plan to keep playing until someone tells me to stay home — or at least sit on the bench.”

This year, Agudath Sholom kept up its dominance with a decisive 8–0 shutout. But watching the handshakes, smiles, and good-natured banter after the final out, it was clear that the Kiddush Cup had no losers. In the end, the real winners were the two shuls—and the community that has grown stronger together with every Labor Day game.