Fortune Favors the Brave
Fortune Favors the Brave
Book Review: Lucky Loser, by Michael Kosta
Book Review: Lucky Loser, by Michael Kosta
By Patrick J. SauerMarch 11, 2025

Daily Show host Michael Kosta approves of last year's U.S. Open. // Getty

Daily Show host Michael Kosta approves of last year's U.S. Open. // Getty
What Matthew Brady’s stark black-and-white photographs were to bringing Civil War realities to the American masses, The Daily Show is to splaying out the ongoing carnage in the Battle of Tennis vs. Pickleball.
It’s a decent seven minutes of your day, mainly thanks to Patrick McEnroe’s faux disdain for the announcer gig and sincere love of sriracha mayo, but what takes it to another level is the intrepid journalist at the center of the controversy, Michael Kosta. I dipped out as a regular Daily Show viewer years ago, so it never came to my attention that in 2017, a former Challengers Tour pro had joined the “Best F**kin’ News Team” as a correspondent and now serves as one of the rotating group of hosts along with that other conquering collegiate jock. Hell, I wasn’t even aware of the pickleball skit until after I donned my reviewer’s reading glasses and tackled Kosta’s Lucky Loser: Adventures in Tennis & Comedy.
I mention my coming in blind and deaf to Kosta because it worked out not having his “everything always works out for me, the handsome white dude” Daily Show persona in my head. I mean this in the best way when I say Lucky Loser isn’t all that funny, at least in the setup-punchline trap comics often bring to their books in lieu of exploring deeper feelings. Conversely, unlike so many of his stand-up peers, Kosta isn’t a self-loathing basket case probing the depths of a fucked-up psyche on the page. Refreshingly, what Lucky Loser delivers is a sincere, charming, affable—even, a few times, moving—ode to tennis and family, both the one he was born into in Ann Arbor, Mich., and the one he was recruited into at the University of Illinois.
Lucky Loser is divided into four sections, with the Springsteen-y opener “Growing Up” being the strongest because his fun-loving upper-middle-class childhood is so grounded and relatable. Today, Kosta may not be selling out arenas, but he’s certainly made it in terms of a successful comedy career, so from the outset, the stakes of the book aren’t that high. Kosta will deliver readers unto his first Tonight Show appearance, but the soul of the book comes early on in his young tennis life. From those long summer days of banging balls alone off the garage door, to endless hours spent at the Racquet Club, where a $600 membership got the Kostas “eight hard courts, four clay courts, a backboard, a swimming pool and a grass yard,” to a touching remembrance of older brother John consoling him on court as he wept while losing the vaunted “Boys’ Under 10 Final” 6–4, 6–4 to Bradley Adams. (One recurring winner is Kosta throwing out actual competitors’ names and footnoting where they are now. Adams coaches the men of Villanova; another guy is a banned Vegas poker player who ran multiple scams and went AWOL in 2011.)
The sporting anecdotes are uniformly strong in Lucky Loser, and they aren’t all for laughs. They range from the ridiculous—Kosta’s Illini coach being obsessed with clean-shaven faces no matter the Pete Sampras stubble—to the harrowing. One morning, Kosta and two teammates got into a rural “two-car-totaling crash” (100 percent the old boy-making-a-U-turn-on-the-highway’s fault) on the way to an opening-round Futures match, only for our hero to finagle his way from the scene of the accident to the tourney, where he earned his first ATP point.
Details of matches gone by are also sharp. Kosta vividly recalls a loss on Korea’s Jeju Island in which he choked away a 5–1 third-set lead, got so mad he walked back to the hotel, and ended up in a random market filled with hideous-looking marine life. What’s tellingly hilarious about Kosta’s tennis-brained recollections of Jeju is that I had the good fortune to visit a few years ago and can attest: It’s one of the most beautiful and engaging places on the planet. Just a mention of Jeju in Kosta’s book drifted me back to its golden beaches, the dormant volcano, the explorable lava tubes, the Haenyeo women who practice the ancient skill of free-diving for seafood, a delicious island breed of black pig known as the “wagyu beef of pork,” and the K-Pop Museum hologram show enjoyed by my wife and then-6-year-old daughter alongside an uncomfortable number of overly enthusiastic childless middle-aged men.
Then there’s Kosta on Jeju: “I was staring at this disgusting blowfish and I let my brain wander to the happy days of tennis, when it was the safety of home, the comfort of family, the protection and innocence of childhood…. I never want to experience that feeling of loneliness again.”
Athletes, they’re not like us!
There are enough meaningful passages to take Lucky Loser beyond a simple sentimental journey, but to put it in proper terms, the book isn’t without faults. There are multiple international first-person sex scenes that quite frankly aren’t filthy, witty, or embarrassing enough to move the needle, as it were. There is one amazing ribald moment of debauchery involving a Japanese host family, a horny daughter, an angry father, and a dog yakkin’ on a prophylactic, but it belongs to a suddenly homeless teammate. Kosta never reached such lows, so his encounters like the spontaneous Catholic-school-clad woman and the Tokyo bathroom akume feel Treetorned in as fodder for the stunted white male comic podcast universe. (A savvy bookselling play given every goddamn last one of them has one…including Kosta himself, natch.)
Speaking of shoehorning, there’s an odd coincidence that needs addressing for longtime followers of the Second Serve literary desk. Much like the time in the late ’90s when there were two separate major motion pictures about Oregon long-distance runner Steve Prefontaine, Lucky Loser shares a lot of its DNA with last year’s fantastic life-on-the-tennis-margins work, Conor Niland’s The Racket. That book is grittier, grimmer, and devoid of Kosta’s nostalgic bent, but the Irishman also had a lot more to lose. Niland topped out at #129 and played in two majors; Kosta peaked at #864 and didn’t… But Niland isn’t getting coffee with Jon Stewart, either. Neither of these memoirs is a taxing intellectual lift, though, so to get your tennis fill, don’t put them in competition; take them in tandem. Two road warriors (who crossed literal college paths during Niland’s UC-Berkeley days when Kosta took him down in straight sets) telling tales from the same side of the defeated net. Doubles partners in literary arms.
Tennis players rarely go out on the terms they envisioned, but even when they do, they have to come up with a second act of their young lives. For Kosta, failing and bailing on a Korean paradise put him on the path to make a ballsy leap. He went from a solidly secure home-owning Big Ten daytime assistant coaching gig with the Wolverines/nighttime Ann Arbor stand-up favorite, to the unpaid Los Angeles abyss known as open mic night at the Comedy Store, and on to swigging Heinekens with longtime tennis buddies in Jay Leno’s greenroom. What Lucky Loser makes tenderly clear is that Kosta’s remarkable journey, in either world, is due to the unwavering support of the family he loves. If there is a singular influence to sum it all up, it would be the Halloween his parents went as Monica Seles and the German asshole who stabbed her.
Tennis and comedy, together at last. But pickleball is no laughing matter. Michael Kosta is right, it needs to be stopped.

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