On October 1, 2021, at exactly 1:62 PM EST (a deliberate marketing tie-in to the number 162), Lolly Sports released the 50 units of Batch #162 exclusively via their Instagram shop. The price? A steep $499 USD—nearly double the cost of their standard Lolly boot.
While the surface of Lolly Sports 162 is undeniably cute and commercial, there is a subtle commentary lurking beneath the veneer. The title combines "Lolly" (sugar, sweetness, childhood) with "Sports" (competition, adulthood, structure). By merging the two, Kasey and October seem to suggest a return to a time when play was pure, and competition was friendly.
In a modern world where sports are often mired in politics, money, and intense pressure, Lolly Sports 162 offers a sanitized, idealized version of athletics. It is a visual escape, a reminder of the simple joy of picking up a ball or running across a field, unburdened by the complexities of the adult world. It is a "Lolly" version of sports—sweet, consumable, and leaving a pleasant aftertaste.
There are seasons that blend into the next, and then there is October Lolly Sports 162 — the one that Kasey still dreams about, sometimes in grainy VHS static, sometimes in vivid, slow-motion sugar-rush color.
Kasey wasn’t a star. In the grand ledger of the October Lolly League — a small-town, end-of-autumn athletic tradition where the prize was a hand-dipped lollipop the size of a dinner plate — Kasey was listed as “utility sub, unconfirmed.” But legends don't ask permission. They borrow cleats, show up early, and remember the score nobody else bothered to write down.
162 wasn’t just a number. It was the final game of the season. The last possible contest before the first frost killed the outfield grass and the field reverted to a pumpkin patch. 162 games — an absurd, beautiful marathon for an amateur league that met only on Sunday afternoons in October. How did they play 162 games? They didn’t, not really. That was the joke and the curse. 162 was the season that never ended, the one the town kept extending because nobody wanted to say goodbye. Kasey And October Lolly Sports 162
By Game 162, the lollipops weren’t just candy — they were trophies, bandages, currency, and sometimes, apology gifts. The October Lolly rule was simple: each team earned one massive, hand-swirled lollipop per win, flavor chosen by the winning pitcher. By Game 162, Kasey’s team — the Sour Apple Underdogs — had exactly one lollipop. The opponents, the Caramel Kings, had 97.
The stadium (a faded bleacher with exactly 14 functional seats) was barely half full. October wind had turned cruel. The Sour Apple dugout smelled of wet wool and desperation.
But here’s what the scoreboard didn’t show: Kasey had been benched all season. Game 162 was supposed to be mercy-ruled by the third inning. Instead, it became the longest game in league history — 22 innings, lasting until the county fair’s Ferris wheel lights flickered on in the distance.
In the top of the 21st, the Caramel Kings’ star slugger hit a line drive that should have ended it. Instead, it ricocheted off a loose bolt in the right-field fence and landed directly into the glove of Kasey’s backup mitt — the one with the broken strap held together by a twisted red licorice lace. Kasey had been hiding in right field for four hours, shivering, untouched by the ball. Until that moment.
The catch didn't make the local paper. But the girl selling hot chocolate recorded it on a flip phone. Years later, that 14-second clip would be called “The Candy Catch” in a small documentary that 3,000 people watched online. On October 1, 2021, at exactly 1:62 PM
Bottom of the 22nd. Two outs. Bases empty. Kasey, who had never batted in an October Lolly game, was sent up because everyone else had already left to go home and make dinner. The pitcher yawned. The umpire checked his watch. Kasey swung at the first pitch — a slow, clumsy arc of maple and hope — and made contact. Not a home run. Not a base hit. Just a slow dribbler between first and second that the Caramel King’s second baseman, distracted by a phone call about a broken tractor, failed to field cleanly.
Kasey reached first base. The game didn’t end there — because the rulebook had a forgotten clause: in Game 162, if the Underdogs scored at least one run after the 20th inning, the final lollipop of the season would be awarded not to the winning team but to the player who “most exemplified the spirit of October Lolly.” The vote was 7–3 in Kasey’s favor. The lollipop was enormous — blood orange and honey — and it cracked in half when Kasey tried to hold it.
Kasey gave one half to the Caramel Kings’ pitcher, who had thrown 204 pitches that day. The other half melted in the car on the drive home, staining the passenger seat like a small, stubborn sunrise.
October Lolly Sports 162 didn’t have a winner. But it had a Kasey. And sometimes, that’s the whole point of keeping score — not to crown a champion, but to prove that even in game 162 of a season nobody was supposed to finish, someone showed up, caught a miracle with licorice lace, and made contact.
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Kasey & October Lolly Sports – Season 162: A Tale of Grit, Growth, and Glory
One of the most informative aspects of Lolly Sports 162 is its technical execution. In an era where digital art often attempts to mimic 3D hyper-realism, Kasey and October lean hard into "flatness."
This is a deliberate stylistic choice. By removing gradient shading and hyper-realistic textures, they reduce their subjects to pure form and color. This technique, often associated with "Flat Design" in graphic arts, allows the colors to pop with an intensity that feels almost backlit. In Lolly Sports 162, the color palette is not just an aesthetic choice; it is the emotional engine of the piece. Bright reds, electric blues, and sunny yellows interact to create a sense of optimism that is increasingly rare in contemporary art discourse.
| Category | OLS | League Avg | Rank | |----------|-----|------------|------| | Runs Scored | 845 | 711 | 1st | | Runs Allowed | 632 | 689 | 2nd (fewest) | | Team OPS | .856 | .795 | 1st | | Team ERA | 3.41 | 4.02 | 2nd | | Fielding % | .986 | .978 | 1st | | WAR (Team) | 42.5 | — | 1st |
The numbers tell a simple story: October Lolly Sports were the best offensive team in the UPL while also fielding the league’s toughest defense. Their +213 run differential (+1.32 per game) was the highest margin in the past decade.