Although it has been almost a full month since Theo Epstein’s end-of-year press conference, it’s hard for any die-hard Cubs fan to forget anything the Cubs’ president mentioned that day. He preached change, change, and more change. Both at the manager spot, with eventually hiring David Ross, and the roster. It was refreshing to listen to, as every Cubs fan’s last wish is to see the front office sit on their hands again like they did last winter. However, although there is, in fact, a new manager headlining the 2020 Chicago Cubs, it feels like nothing, in fact, has changed. Theo Epstein admitted about falling into a “winner’s trap” the last three seasons in regard to not trading players who helped the Cubs win the 2016 World Series, and it took him not even one month to fall into the exact same trap.

I understand that David Ross is not Joe Maddon Jr. With all the information that has resurfaced the last few weeks in addition to Monday’s press conference and Ross’ public statements, Ross is going to have no problem holding his friends on the roster accountable. If he felt comfortable doing it as a player, it will be easier for him as a manager. He was quoted last week saying he will demand the best out of each player on a daily basis, which is a massive upgrade from Joe Maddon. Maddon’s ‘loose ship’ approach ran its course as the players aged and egos started to settle in, and that will not be how this team is managed in 2020 and beyond. Ross is also an exceptional leader of men who guys rally around and want to play for, so the 2020 Cubs are in better hands at manager than the 2019 Cubs were.

But even if Ross is an upgrade from Maddon, that does not mean the front office made the right decision on whom to hire. If your rationale for hiring Ross is due to how well the Cubs’ culture was in 2016 and how it resulted in a World Series, isn’t that the EXACT same winner’s trap you said you fell into in regard to not trading the Cubs’ core? Instead of looking back at 2016 and trying to apply it to 2020, they should have objectively looked at each candidate’s present-day merits. If they did that, they would have found that Astros’ bench coach Joe Espada is by far the more qualified candidate. It is not close. He has more managing experience than David Ross, as he worked under Brian Cashman in the past, in addition to having a deeper understanding of analytics, which was acquired from his time with the Astros. Theo Epstein, Jed Hoyer, and Tom Ricketts hired David Ross because of familiarity, not because he is the best candidate. Anything mentioned of the contrary is false.

Joe Espada would have brought an impressive analytical background to the Cubs that would have positively changed the organization’s fundamental strategy towards winning, but Theo elected to hire David Ross because he was the more familiar candidate.

While I do believe hiring Ross will invigorate a new culture in the clubhouse and the organization will be better off in the short and long term because of it, the front office had an opportunity to completely revamp how the organization looks at baseball from a strategy standpoint. Theo preached in his press conference a month ago that the Cubs are analytically behind what other teams like the Houston Astros, Tampa Bay Rays, Oakland Athletics, and Los Angeles Dodgers are doing, yet you elect to go with a guy with no analytical background? They had an opportunity to steal innovative analytical intelligence from an organization that has won 100 games in each of the last three years (and potentially two World Series titles), is the alpha in terms of analytics in baseball, and is doing things with spin rates for pitchers that nobody else in baseball is mirroring. Yet they went with a guy due to familiarity. That’s illogical. Other than culture, nothing about the 2020 Cubs will be different. I do believe Ross will have success and the 2020 Cubs will be better than the 2019 Cubs, but Espada would have completely altered the course of the organization in a positive direction. It just feels like Theo and Jed continually try to recreate 2016. While other organizations are ascending and improving their organizational strategy, the Cubs are going backward.

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