Songfacts®:

• While the exact dynamic between Conan Gray and the song's subject remains a mystery - could be an ex or family member - one thing is clear: Gray's mission is to spotlight the self-absorbed and hurtful nature of this individual.
  
  Picture this: not a soul out there has mastered the art of bringing me down quite like you. Congratulations, you've won. This character cunningly tried to twist Gray's reality to their advantage, but now by crowning them the "victor," Conan flips the script, seizing control over the whole twisted affair.
• In verse two, Gray's done with them. Now they're crawling back, missing the singer.
  
  My heart that once was beating
  Bleeding in the palm of your hand
  Yet, you have the nerve to miss me
  How do I somehow feel guilty
  When you're the one who let it get this bad?
  
  Guilt creeps in for Gray even though the other person brewed this mess.
• Gray wrote "Winner" at 2 a.m. at the piano when everything just spilled out all at once. "It was a moment where I finally felt like, 'fine. great job. you did it. you hurt me more than anybody ever could hurt me,' and it oddly felt nice," he said. "I see now that there is a certain freedom that comes from recognizing that you've been hurt. in no longer running, and just facing the fact that 'you win. you hurt me.' I hope this song helps people find a little piece of that freedom."
• Conan Gray co-penned "Winner" with Greg Kurstin, an American record producer, songwriter, and multi-instrumentalist. He has worked with some of the biggest names in music, including Adele, Paul McCartney, Sia and Kelly Clarkson.
• Kurstin played all the instruments: strings, guitar, bass, synthesizer programmer, piano, Mellotron, keyboards, percussion and drums.
• Conan Gray officially previewed "Winner" during his August 12, 2023 set at Outside Lands Music Festival. He released it as a single a fortnight later.