Teams for the NHL Winter Classic are not chosen by a strict formula, but by a mix of business, TV, and hockey-storyline decisions made by the league office each year.

Big picture

  • The league office hand‑picks the matchup; there is no automatic qualification like “best record” or “last year’s champion.”
  • The goal is to create a spectacle : big TV audience, great visuals in the stadium, and a matchup that casual fans recognize.

What the NHL looks for

  • Market size & TV draw: Teams from big media markets or with huge fanbases (Rangers, Bruins, Blackhawks, Penguins, etc.) get picked often because they reliably pull strong ratings and ticket demand.
  • Rivalries & storylines: Classic or recent rivalries are gold—Original Six matchups, regional grudge matches, or playoff rematches are all attractive because they give networks an easy narrative to sell.
  • Star power & current relevance: Clubs with marquee players or teams expected to be good that season are more likely to be chosen so the game looks like a high‑end showcase, not a slog between rebuilding rosters.

How the host city gets picked

  • Stadium and city appeal : The NHL looks for football or baseball stadiums that can be turned into an outdoor rink and provide a visually striking backdrop—iconic parks, downtown skylines, or unique settings.
  • Logistics & climate: The venue needs to handle massive crowds, TV infrastructure, and the quirks of outdoor ice; colder‑weather markets are naturally easier, though the league has pushed the envelope over time.
  • Local support & politics: Team ownership and the city have to want it—there’s a lot of cost and planning involved, so the NHL works with willing partners that can sell out the building and embrace the event.

Rotation and “fairness”

  • Every franchise has reportedly expressed interest in playing in a Winter Classic at some point, but popular teams do get repeat invites because they’re proven draws.
  • Behind the scenes, the league tries to slowly spread opportunities around—mixing in teams that haven’t had an outdoor showcase yet with legacy brands that guarantee numbers.

Why it can feel “rigged” for the same teams

  • Fans on forums often joke that step one is “decide if Chicago or Pittsburgh is in it,” and then find a rival for them, reflecting how often certain brands appear outdoors.
  • That repetition is less about favoritism on the ice and more about maximizing ratings, sponsorship value, and national buzz in what the NHL treats as a tent‑pole TV event.

TL;DR: There’s no standings‑based rule—teams are picked by the league to balance big markets, rivalries, star players, and a host city that can deliver a TV‑friendly outdoor spectacle.

Information gathered from public forums or data available on the internet and portrayed here.