One of my personal headcanons is Jack faces a Gretzky-esq situation where he leads the Falconers through a few dynasty years but when the team goes into rebuild mode he gets traded. Montreal, eager to say they have a Zimmermann back in Quebec, picks up the contract immediately.
Using that as a jumping off point for your ask: when a 35-year-old Jack returns to Montreal with his husband in tow, Bitty finally achieves his dream of experiencing ‘Roll Up The Rim’ season firsthand.
(That said, when Peyton Manning went to Denver and became a spokesperson for Papa John’s, part of his compensation was a stake in like 30 Denver area franchises.
Imagine Jack becoming the face of Tim Hortons in Quebec and coming home like ‘haha Bits, we own like ten Timmys now,’ and Bitty being horribly devastated because ownership disqualifies you from winning promotional prizes.)