loserest
adj- Team captains took money on the side, so even the loserest ball player could pitch an inning.2007, Chuck Palahniuk, Rant: The Oral History of Buster Casey, page 52:
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Informal Most like a loser; most pathetic or worthless.
- With that, he hastened out of the room as if his pants were on fire, leaving poor Gabriella to marinate in her embarrassment, feeling like the loserest of losers, after having been completely shunned by a man.2016, Jenny Gardiner, It's Getting Hot in Heir: