About The Winter in Shorts
The Winter in Shorts
Jake Diamond
In the fluorescent-lit corridors of suburban Toronto malls, Deren the Baron reigns—armed with nothing but a fanny pack, athletic shorts in January, and the unshakable conviction that the world owes him its gaze.
He’s always sharing: his pranks, his raps, his relentless pursuit of teenage boys who might finally make him famous. The internet watches, laughs, and slowly morphs into something hungrier.
As bans stack up like snowdrifts, shelters bolt their doors, and the fragile line between fan and predator dissolves, Deren’s winter turns colder than the Canadian night. What starts as cringe comedy spirals into a raw, unflinching portrait of addiction, delusion, and the terrifying price of going viral in the 2020s.
Darkly funny, deeply unsettling, and impossible to look away from, The Winter in Shorts is the tragicomedy of one man’s unstoppable descent—and the quiet, devastating moment the world finally turns its back.
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Author Bio:
Jake Diamond is a pseudonym. You might recognize him from Kyle Benjamin Kesselman: A Story Told in One Room.
Jake wrote both books in the Fall-Winter of 2025. They’re not a series but they definitely share some characters, as well as the same Toronto street,