What Can We Learn from Baseball's Losingest Winner?

I was a child, maybe eight or nine, when I learned about baseball’s Cy Young Award. Given to the best pitcher (as voted on by esteemed baseball writers) in each the American and National League, the award was posthumously named for baseball’s all-time winningest pitcher - Cy Young. Without knowing anything else about Cy Young’s career other than his wins total, I understood why he would be synonymous with baseball's best pitchers, since wins were the golden metric for evaluating a pitcher’s excellence.

With 511 wins, a record cemented as one of the untouchables in American sports, Cy Young was indeed brilliant. Yet over the past seventy years, Cy Young voters have evolved away from using a pitcher’s win total as the holy grail of criteria. In the 50s and 60s, Cy Young winners trended towards pitchers with high wins totals who led their team to the World Series, then in 80s and 90s it leaned towards pitchers with the highest total of wins in spite of ERA. At the turn of the century, voters chose to combine wins with weightier stats like ERA/WHIP. Now voters favor advanced analytics with wins now relegated as a second-class metric.

Paralleling the ever-changing criteria for the award, my interpretation of the award - the symbolism of Cy Young - has evolved too.

As mentioned, the first thing I learned about Cy Young was his record for most wins. But a few years later, once I turned fourteen, I learned something specious about this award’s name-sake. Cy Young also has the most losses in MLB history.

Yes, the award for the “best pitcher” is named after someone who was the “biggest loser”.

I couldn’t wrap my head around this. Being young and naive, I wondered how the MLB could have overlooked this fact.

The award was inaugurated in 1956, four decades after Young’s career ended. This meant that baseball had witnessed dozens of other pitchers of which to name the award. There weren’t just those with fewer losses than Cy, but also with a better winning percentage.

In fact, Cy Young is only 88th in history in win percentage - with more than half of those 87 pitchers having finished their career before 1955.

But now that I’m decades wiser and no longer armed-and-ready to accuse this award of being a farce, I’m able to dive deeper into what can be learned by immortalizing the losingest pitcher in baseball.

From Cy Young’s propensity for winning AND losing, I think about how one should treat, compare, and weigh our personal “wins” and “losses”, ranging throughout different aspects of life.

Let’s start with the entrepreneurial space. Any innovator or start-up business owner who strives for success will endure many losses along the way. In building a company, they’ll be required to take risks in figuring out what’s financially viable instead of theorizing and ruminating on the perfect way to start. False leaders may stay stagnant, sitting on their hands, awaiting all the variables to align out of fear of going down a misguided path. But those that act and move forward will inevitably lose…on their way to victories.

I also started thinking about the losses that come from not getting what you want or, more succinctly, rejection.

Socialite media mogul Dan Bilzerian, who is known for his lavish lifestyle decked out with beautiful women around him, initially dealt with a barrage of losing. In an interview detailing his college experience, he mentioned his ability to “get girls” because he wasn’t afraid of rejection. Relative to friends who were afraid of getting rejected, Bilzerian was okay with being turned down. He received more losses than other shyer boys, but also got way more wins.

In this way, losing builds a callous and you become numb.

Perhaps there’s no better business example than cold calling. This sales strategy of “smile and dial” leads to an incredible amount of rejection, occasionally in the form of personal attack. But with more at bats or swings (sorry for the hitting metaphor) you’ll get the opportunity for more pitches (there, brought it back to Cy Young), and you’ll receive more sales.

From Bilzerian to BDRs, the overall denominator of opportunities matter. We know Cy Young had the most all-time wins and losses, but it’s now time I share with you that he also had the most starts, most innings, and most batters faced in history.

In the same way Cy Young shouldn’t be judged on win percentage, it’s hard to get an accurate representation looking at our life’s win percentage. Especially, due to the imbalance of how we present life’s wins and losses.

Ask anyone who sees our social media, reviews our resume, or answers small talk of “how’s it going?”. Situations requiring an external means for approval will make us seem like we have a win percentage of 1.000.

Hyper focusing on our life’s wins column doesn’t equate to reality, but there is a psychological phenomenon explaining doing so is human nature - not just for our personal validity, but how we evaluate others. It turns out that when we assess one’s level of achievement, a person with as many successes as failures will be associated with their successes.

Donald Trump is a great example. Within his portfolio of business, the American public (on the whole) associates him more with a successful real estate empire, golf courses, and billions of dollars over his failed steaks, airlines, university and multiple bankruptcies.

Returning to sports, I can complement Cy Young with the polarizing on-field resume of another great athlete - Brett Favre. Favre exited his career with the most touchdowns ever thrown and because of that was hailed as one of the best QBs. But he also owns the record for most interceptions.

Considering football autocrat Bill Belichick handpicked Favre on his NFL 100 All-Time team, there must be more than meets the eye to leading the NFL in a most ominous stat.

To dissect Favre’s yin and yang is to remind ourselves that his best ability was availability. Favre’s consecutive start streak of 321 consecutive games gave him ample opportunity to lead both categories of respective bravado and humility. Yet just like with Cy Young, we associate Favre with his winning play than with his losing play.

There’s a common maxim “history is written by the winners”. But a more accurate rephrase is “history is written by winning.”

Winners lose. A lot.

Now that I’m 33 and addressing my own personal crossroads, perhaps Cy Young - our protagonist with the most losses but also the most wins - can embody an important personal philosophy.

As someone who fixates on losses, I need to embrace my victories as well.

I need to stop framing my memories around the negative space and build it around the positive. I have to rework my susceptibility to counting days where I don’t accomplish anything vs. those in which I make great strides. When on days if I feel isolated, I need to reflect on the plethora of times (both past and recent) where I’ve been extremely social, sometimes even the life of the party. This maladaptive focalism comes at the expense of realizing the great things I have in life: plethora of friends, breadth of network, and a healthy, united family.

When it comes to my freelance work, I mentally regress when I think about times I’m stuck and feel unable to grow my business. Unfortunately this comes at the expense of discounting those days where I accomplish many goals - signing new clients, publishing articles like this, and continuing to pursue this career which gives me fulfillment.

A focus on losing can spiral into a self-fulfilling prophecy. Plus, compiling losses within a vacuum may lead to detrimental identification as a “loser.” But I doubt athletes like Young and Favre (and certainly not the braggadocios Trump) ever looked at their failures and thought any less of their virtues - ability, grit, and desire to win. They view themselves as winners and their vice-like stats as byproducts of achieving greatness.

Losing is essential to one’s journey and those who accumulate the most losses work hardest towards ultimate success.

Losing demonstrates that activity is more important than an inactivity rooted in one’s preservation of perfection.

Cy Young didn’t lose the most games in MLB history because he was bad, but rather because he gave himself the most opportunity to compete - a great lesson for business, friendship, romantic relationships, or any other domain that makes us vulnerable.

I’ve chosen to appreciate Cy Young through both his wins and his losses. I need to appreciate my life the same way.