My rebbe, Rabbi Berel Wein, related that shortly before he made aliyah in 1997, he took some of his grandchildren to a Yankees game at the old Yankee Stadium.
It was a close game, and the Yankees lost in extra innings. The mood in the stadium was very melancholy as the Yankees faithful slowly and grumpily exited the stadium.
As they were leaving, one of his grandchildren asked Rabbi Wein, “Zaydei, how come you’re not upset about the loss like the rest of us?” Rabbi Wein replied, “Because I’m a Cubs fan. We haven’t won a World Series since 1908. We are used to losing, so today’s loss is no big deal.”
Rabbi Wein mused that a person has to know how to live with struggles and defeats, because failures and disappointments are inevitable and par for the course in life. A successful person is not one who never fails, as much as it is one who knows how to traverse setbacks and not allow them to completely derail him.
Well, in the wee hours of November 3, 2016, the Cubs have finally won a World Series. There’s no one alive today who remembers the last time they won, but the lovable losers have finally become winners.
So now the question becomes whether a team that has lost for so long can deal with such a significant win.
Not surprisingly, this is another lesson Rabbi Wein taught us: A person has to know how to deal with success, and how to capitalize on it, and how to use it to benefit others. Tragically, there are many people who are destroyed by their own successes because they don’t know how to handle them or how to capitalize on them.
In our world, many of us struggle with a balance of both of these challenges. On the one hand, we are blessed to live in such an affluent society with so much opportunity. Yet, on the other hand, we struggle to keep up with the impossible financial demands of living in such a world. This includes yeshiva tuitions, the expenses of Shabbos and yomim tovim, and all of the other expenses involved in living an elevated Torah life.
The Mesilat Yesharim cautions us that everything in life is a challenge—poverty is one type of challenge, affluence and wealth is another. The main thing is that we always seek to make the best out of every situation, as we think Hashem wants from us.
So Cubs fans, enjoy your moment of glory—make sure use you celebrate wisely.
As for Cleveland Indians fans, sorry that Lebron couldn’t save you this time. If the Cubs are any indication of how long it takes to break out of being “lovable losers,” you’re due to win the World Series in 2057.
By Rabbi Dani Staum
Rabbi Dani Staum, LMSW, is the rabbi of Kehillat New Hempstead.