When winning is the only moral test

Sports make this rule easier to see because bodies fail in public. Over the weekend at the Milano Cortina Olympics, Lindsey Vonn pushed her body through years of injuries to a devastating crash because elite competitors too often don’t get clean endings. When her career effectively ended that day, the reaction was split. There was admiration for the fight and criticism that she should have known when to stop. In the ethos of public opinion, however, the criticism appeared to center more on her refusal to exit on a culturally acceptable schedule — that she was taking a space that should have been used by a younger athlete. 

Now set that beside Tom Brady. He extended his career far past what most quarterbacks are encouraged to do. As long as the wins held, longevity became proof of exceptionalism. The same decision was praised as vision rather than stubbornness. Coverage made the distinction clear: winning validates the risk, losing retroactively condemns it.

This culture of winning also governs how we tend to also judge founders, CEOs and our elected leaders. Stay too long and succeed, and you’re a visionary who is paving the way and refuses to be limited by outdated expectations. Stay too long and fail to deliver, and you’re accused of blocking the next generation. We claim to be debating humility or responsibility, but we’re mostly retroactively reading the scoreboard and calling it ethics.

There is another underappreciated path, one where influence evolves and the system grows stronger because of it.

In the final years of Megan Rapinoe’s career, she was still very much a star but she used that visibility differently. Rapinoe amplified younger teammates, pushed structural fights like equal pay while her leverage still mattered, and normalized leadership that didn’t require being the center of gravity. When she retired, the U.S. Women’s National Team didn’t need to scramble to replace her because leadership had already been redistributed. Rapinoe made this possible with her own brand of exceptionalism that is far too undercelebrated. 

The same logic applies at institutional scale when leaders treat succession as part of the job rather than an afterthought. Satya Nadella didn’t revive Microsoft through sheer force of personality but instead rewired the culture to focus on internal mobility and collaboration that then became expectations. Senior leaders were evaluated on whether they produced other leaders, and collective winning became the value driver.

This distinction matters, because organizations and movements built around a single irreplaceable figure are fragile by definition. Nadella’s contribution creates durability so when he chooses to step aside, Microsoft won’t face an identity crisis. This outcome is the result of treating succession as organizational architecture.

What’s striking is how rarely we celebrate this kind of leadership while it’s happening — there is simply no trophy for restraint and no viral moment for mentorship. Credit often accrues to whoever comes next, which makes the work easy to miss. This kind of leadership only becomes understood in hindsight, once the transition holds and the institution doesn’t wobble. By then, the moment for recognition has passed, and the discipline required to replicate its success is forgotten. Our culture well understands how to reward the win and dissect the loss, but it really struggles with much in between.

The uncomfortable truth is that American exceptionalism trained us to equate worth with winning, and in the wake of all of that, many of us never learned how to both appreciate and execute plans that create the legacies we want to see or put in the necessary work to bring those plans to life. But in the game of life, anyone claiming certainty for an outcome yet to happen is usually protecting a preferred ending. What I do know is this: cultures that only reward the win then lose the capacity to judge decisions independent of outcomes. And the cost of that omission isn’t paid by today’s winners — it’s paid by the next generation, inheriting institutions, norms and expectations shaped by hindsight rather than responsibility or vision.

If I counted correctly, this is my 100th column writing for the Daily Journal. It’s been an absolute pleasure and gift to be able to write for you every week. Thank you for sharing this journey with me.