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Winter Olympics films: what CTOs can learn from underdog narratives

As Milano Cortina 2026 approaches, streaming platforms are recycling Olympic documentaries and dramas. The pattern reveals something tech leaders know: transformation stories sell better than they execute. Here's what century of Winter Games films actually tells us about performance under pressure.

Winter Olympics films: what CTOs can learn from underdog narratives

The recycled playbook

Winter Olympics content follows a predictable cycle. With Milano Cortina 2026 eighteen months out, streaming services are repackaging the same dozen films: Miracle (1980 U.S. hockey upset), Eddie the Eagle (first British ski jumper since 1928), I, Tonya (the Harding-Kerrigan scandal that dominated 1994).

The titles change but the narrative template doesn't. Underdog team beats impossible odds. Athlete overcomes systemic barriers. Scandal exposes uncomfortable truths about winning at any cost.

What actually happened

The facts behind these films are more instructive than the dramatizations:

  • Jamaica's bobsled team—inspiration for Cool Runnings—returned in 2022 with both male and female squads. The original 1988 story was substantially exaggerated for drama.
  • The Schultz brothers in Foxcatcher were the first Americans to win wrestling golds in the same Olympics. The film ended with murder.
  • Downhill Racer (1969) remains technically accurate about alpine skiing. Most others prioritize narrative over accuracy.

The pattern tech leaders recognize

Every Olympics film follows the same arc: announce ambitious goal, face setbacks, achieve unexpected success through determination. Sound familiar?

It's the same structure vendors use for digital transformation case studies. The difference: Olympic films acknowledge the cost. Herb Brooks' players in Miracle trained obsessively for months. Eddie Edwards became a joke to much of the skiing establishment. Tonya Harding's talent was real; so was everything that destroyed her career.

Transformation isn't a montage. It's sustained effort, trade-offs, and often failure.

Worth noting

The best Olympic films—Downhill Racer, early documentaries—focus on process over outcome. They show what performance under pressure actually requires. The worst ones suggest inspiration alone drives results.

CTOs know better. So do athletes who've actually competed.

The 2026 Games will generate new stories. Some will become films. The template won't change. Neither will the gap between Hollywood's version of achievement and what it actually takes to ship.