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Rabbi Danny Wolfe 09/19/2025

The High Holidays– Win; Don’t Lose

A great modern philosopher, Mike McDaniel, head coach of the Miami Dolphins, recently said something extremely profound: In order to win games, you have to win games, and not lose games.”

How true these immortal words are. Not only in making me feel better about the egregious penalty called against the Broncos that cost them the game last week (because at the end of the day, they lost, and didn’t win), but also in preparing me for the High Holidays that are now upon us. 

The truth is, the Rambam writes something (arguably) very similar. In his classic work Hilchos Teshuva, he famously describes how every year on Rosh Hashana, our merits are weighed against our shortcomings. If we have more merits than shortcomings, we are inscribed and sealed in the book of life. If we have more shortcomings than merits, we are not—and if it's a tie, then our judgment is suspended until Yom Kippur. 

Therefore, according to Rambam, a person is meant to view himself as if his merits are in perfect balance with his shortcomings. One good deed, and we can tip the scale towards the side of goodness. And one sin can tilt the scales in the opposite direction. 

In the Rambam’s words, “If he performs one sin, he tips his balance and that of the entire world to the side of guilt and brings destruction upon himself. On the other hand, if he performs one mitzvah, he tips his balance and that of the entire world to the side of merit and brings deliverance and salvation to himself and others.”

Right now, during this High Holiday season, he describes, is the time to focus on going above and beyond. Or, in Mike McDaniel’s words, “to win, and not to lose.” 

Right now, it’s a spiritual tie, and our actions can be the deciding factor to break the tie, and to achieve victory. 

Right now, our people are in a precarious position. The war in Gaza seems never-ending. Every day, it becomes harder and harder to imagine our precious hostages coming home. But the Rambam writes that every good deed we do can tip the scales of humanity towards the side of good. Every time we bite our tongue when someone offends us, we bring merit to ourselves and our entire nation.

Every time we get up in the morning or stop work early in the afternoon to come to minyan and ensure someone can say kaddish, our actions have a massive impact on the spiritual realm. 

Every time we go out of our way to help a neighbor in need, visit the sick, host people from out of town, comfort mourners, or lend a listening ear to someone going through a hard time, we are changing history. 

Please, G-d, we can all be very sensitive in how we act in these next few weeks, as we individually and collectively tilt the scales once and for all to achieve a clear decisive victory. May this coming year be filled with sweetness, joy, and happiness, as we merit the Redemption once and for all.  

Fri, September 26 2025 4 Tishrei 5786