To play devils advocate: If the team wins, the fans will be there. We're now 6 years removed from the WS team. It sucks that it played out this way but, as a comparison, here are key members of the 2016 team that were on the roster in 2014: Rizzo (breakout season in 2014) Baez (hit .169, spent most of 2015 in the minors) Coghlan (traded from Oakland in 2016) Arrieta (breakout 2014) Hendricks (called up down the stretch, pitched great) Rondon Strop Grimm That's 8 guys (and stretching it a lot on Coghlan and Grimm) that were on the team just 2 years before the 2016 team. This is a bad team right now, it's been a bad team for a whole calendar year. Yes, a lot of that is self inflicted, which is garbage, but the fans (which are already showing up) will be selling the place out as soon as the record flips, regardless of the players on the field. Agreed, success (both individual and team) is always going to be the biggest driver. No one bemoaned losing the connection to the success of 2016 when Almora or Russell was kicked to the curb, or got contemplative about the business of baseball when they moved on from Quintana or Chatwood. People are dying to not look at Heyward in a Cubs uni anymore, it's always gonna come down to the belief that they can continue to be successful and play a part in the team continuing to be successful. Those guys were all much different. In Contreras, you have: A homegrown player who signed with the organization at age 17 A player who is at/near his prime and will still be only 30 years old on Opening Day 2023 One of, if not the, best offensive Catcher in the league A player who, by all accounts, wants nothing more than to stay with the Cubs A team leader on and off the field Why wouldn't he be the type of guy that you want to reward with a multi-year deal, or at least attempt to get a deal done? If the team is planning to compete somewhere around 2024-2025, a 32 year old Contreras could still be a key contributor on that team.