Sometimes When You Win, You Actually Lose

A MESSAGE FROM THE PUBLIISHER

Blessed are the peacemakers, for they will be called children of God. —Mathew 5:9

 By Bobby R. Henry, Sr.

The other evening, while having dinner with several Jewish couples, our conversation naturally turned to politics, the state of America, and the direction of our nation under the current administration. As often happens in such discussions, opinions varied, but one thought remained constant in my mind: regardless of who occupies positions of power, those at the bottom of society often continue to bear the heaviest burdens.

My thoughts were immediately directed back to an article I read pertaining to a meeting recently held in Miami concerning the relationship between Blacks and Jews. More than 100 national leaders, including Van Jones and philanthropist Shari Redstone, gathered in Miami for the first National Convening on the Black-Jewish Alliance in over 25 years, aimed at renewing a historic partnership. Hosted by the Exodus Leadership Forum and Redstone Family Foundation, the event focused on combating antisemitism and racism while building a stronger, future-focused alliance between Black and Jewish communities.

During our dinner conversation, I remarked that while the higher echelons of our communities may find ways to adapt and thrive, those struggling on the margins often continue to catch hell regardless of who claims victory.

After dinner concluded and everyone was about to leave, I approached one of the Jewish gentlemen from the table of whom I have the utmost respect for. He is a leader and well-known political figure in our community for his fairness. I quietly said, “Now that dinner is over, let me ask you about the real elephant in the room.”

He looked surprised and asked, “What elephant?”

I replied, “Congressional District 20.”

Immediately, he acknowledged the issue and shared that he had already pledged his support to a particular candidate. Then he mentioned another candidate whom he seemed to believe represented the choice of the Black community.

His comment caught me by surprise.

To my knowledge, there had been no official poll of the Black community. No broad consensus had been reached. No collective decision had been made. Yet somehow, an assumption had emerged that a particular candidate had already been designated as the community’s preferred choice.

I responded with a simple analogy.

“I would never tell the opposing team not to put its best player in the game,” I said. “But I also would not assume that my team has already selected its captain simply because someone outside the locker room says so.”

That brief exchange reminded me of a larger truth.

Too often, decisions affecting communities are made without the difficult conversations that should precede them. Assumptions replace dialogue. Narratives replace listening. Labels replace understanding.

What made this conversation meaningful was not the subject itself, but the setting. I waited until dinner was over. There were no microphones, no social media posts, no audience to impress. Just two people willing to briefly engage honestly about an issue that carries deep emotions and significant consequences.

That is what we are missing in America today.

Whether the conversation is between Blacks and Jews, Haitians and Jamaicans, Cubans and Mexicans, conservatives and liberals, members of the LGBTQ+ community and those who disagree with them, or any other group, we cannot move forward if we refuse to talk openly and honestly with one another.

Not everyone needs to be in every room. But every room where decisions are being shaped should include voices that genuinely represent those who will be affected.

The reality is that progress is rarely achieved through silence. It is built through courageous conversations that acknowledge history, respect differences, confront uncomfortable truths, and seek common ground.

As I reflected on that evening, I realized that the lesson extends far beyond one congressional race.

There are moments when a community celebrates a political victory only to discover later that it has lost something more valuable: trust, unity, representation, or the opportunity to build genuine consensus.

There are times when winning an election, securing a position, or claiming a political prize can come at the cost of relationships, partnerships, and long-term progress.

That is why we must be careful not to confuse victory with success.

True success is not measured solely by who wins. It is measured by whether the people are better off afterward. It is measured by whether communities are stronger, whether voices are heard, and whether bridges are built rather than burned.

Perhaps now, more than ever, is the time to set aside self-interest and focus on what serves the greater good.

Because sometimes, when you win, you actually lose.

And sometimes, the greatest victory comes not from defeating an opponent, but from finding the courage to have the conversation that everyone else is avoiding.

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