Lucky Loser: Adventures in Tennis and Comedy

I truly believe that nothing is better than tennis for building the foundational characteristics of high achievement. The sport builds resilience by forcing players to adapt and problem-solve independently under pressure. Junior tennis players learn to advocate for themselves in the face of adversity. Most significantly, tennis instills a structured work ethic of consistent disciplined effort. The skills and attributes honed by playing tennis extend far beyond the court.

I have been a fan of the comedian Michael Kosta for quite some time. However, when I first heard him characterize himself as a tennis player, my initial reaction was, “Sure, buddy.” It’s easy to dismiss that claim as just another celebrity with delusions of athletic grandeur. As it turns out, he wasn’t kidding. Kosta played junior and collegiate tennis and spent a few years on the ATP tour. He earned a peak ranking of #864. Under the circumstances, I hope I can be forgiven for being unfamiliar with the tennis side of his life until the recent publication of his book.

Lucky Loser: Adventures in Tennis and Comedy is a unique memoir of a life that started in tennis and wound up with success elsewhere. The narrative opens by tracing how Kosta grew up in a tennis family. He competed in junior tennis, played collegiately at Illinois, made a go of it on the professional tour, and adulted for a short stint as an assistant coach at Michigan. From there, Kosta shifts into the second act of his life, an unlikely pivot from tennis into stand-up comedy.

Spoiler alert! By any measure, Kosta is a well-known and highly regarded comic. If you weren’t already aware of that, I feel like I just caught a glimpse into your political leanings, but I digress. What matters here is the tennis, and that’s exactly where this review is focused. Specifically, how well does the book hold up for true tennis fans?

Kosta’s tales of tennis ring true at every level. Whether he’s describing the grind of junior tournaments, the ego clashes of college tennis, or the humbling realities of life on the lower rungs of the pro tour, it all feels authentic. There’s a knowing honesty in how he captures the weird mix of privilege, pressure, and psychological warfare that defines competitive tennis—details only someone who’s been through the trenches could get right.

Pulling back the curtain a bit, when I review a book, I typically mark passages that I think I might want to mention in my review or use as fodder for future blog posts. (I have no idea how real book reviewers work, but that’s the way I do it.) Lucky Loser had an inordinately high number of things that I flagged for mention. Some were beautiful poetic observations about tennis. Others were about what it is like to grow up in a tennis family, including the idea that it never crossed his mind that he didn’t have to play tennis. I can relate.

Ultimately, this story of Kosta’s life is one of resilience. His perseverance on the court resonated with me, as did his raw honesty about how it is more accurate to say that players of his caliber quit the sport rather than retire. For people who have reached the end of the road in their junior, collegiate, or professional journies, Kosta’s account of how he translated the lessons he learned on the court into success in a subsequent career is inspirational. The fact that he wound up in comedy rather than in some corporate boardroom illustrates how broadly the sport’s skills can inform life after tennis.

If I had to make one criticism of the book, it would be that it wasn’t as funny as I anticipated. While Kosta masterfully layers in humor, it wasn’t a laugh-out-loud experience for me. In retrospect, I think his style appeals to me for its subtle, acerbic qualities. The good news is that I don’t think being a fan of his comedy is necessary to thoroughly enjoy this book.

In general, I recommend Lucky Loser for fans of comedy, tennis, or anyone who appreciates a great underdog story. More specifically, I highly recommend it for high-performance juniors who have reached a crossroads of their tennis journey, and one of the options is walking away from the sport. Kosta’s book reminds us that losing is an indelible part of the road to success. What really matters is that the lessons of dogged determination and persistence learned on the court can serve tennis players well in life.

Michael Kosta has given us an unlikely story of how that can be done.

Lucky Loser: Adventures in Tennis and Comedy (<- Sponsored Link)

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