Put yourself in Theo Epstein's position as the head of a multi-billion-dollar corporation knowing that every decision you make could have a franchise-altering outcome. Think that sounds overly dramatic? Well, it isn't.
A quick recap of some of the best moves made by Epstein's administration since he arrived in Chicago from Boston in the fall of 2011 proves that sometimes some of the smaller moves you make on paper can turn out to have a major effect on your team.
When the Cubs traded journeyman pitcher Andrew Cashner for minor league first baseman Anthony Rizzo before the 2012 season, no one could have predicted that Rizzo would go on to become the face of the team and one of the best players in Cubs history.
Another example is the trade the Cubs made to send veteran pitcher Ryan Dempster to the Texas Rangers for two lower-level minor leaguers at the 2012 July MLB trade deadline. For two months of Dempster, the Rangers parted with a solid but unspectacular starting pitcher named Kyle Hendricks who would go on to start and win the 2016 pennant-clinching game over the Los Angeles Dodgers and start Game 7 of the 2016 World Series.
The Cubs best pitcher since Epstein arrived in town was Jake Arrieta who won the 2015 Cy Young Award after coming over alongside reliever Pedro Strop in a deal with the Baltimore Orioles. Arrieta was so underwhelming in Baltimore that he actually began his Cubs career with a stint in the minor leagues at Triple-A Iowa. Strop had an ERA north of 6.00 and was considered a throw-in in the deal. Both men were major factors in the Cubs 2016 World Series title.
So, as we enter the hot stove season in advance of 2020 baseball season the Cubs have to be very honest with themselves about where they are as a major league team and more importantly, where they are as an organization.
Yes, they have some very talented players on their major league roster. However, they also have significant holes in their lineup that at this point keep them from being a serious World Series contender.
They currently don't know who their starting second baseman is although they have high hopes for Nico Hoerner. They don't know who their starting center fielder is. They don't know who their leadoff hitter is and that is an area they have steadfastly refused to address since the Cubs allowed Dexter Fowler to leave via free agency after the 2016 season.
As far as their pitching staff goes, the Cubs have holes in their rotation with at least one definite opening and perhaps more if they choose to upgrade multiple spots. Add in a bullpen that struggled to pitch in high leverage situations in 2019 and you see all of the areas that must be addressed successfully before the Cubs can consider themselves championship contenders.
That means that Epstein, GM Jed Hoyer, and their staff have to be willing to consider any and all opportunities that are presented to them no matter how hard it might be to trade some of the organization's most popular players. They must tune out all of the exterior noise from the Cubs' massive fan base, who as fans don't want to see their favorite players traded.
However, the fact of the matter is that Epstein and Hoyer have offered extensions to every key player on the roster over the past few seasons and only Kyle Hendricks was willing to commit long term to the organization.
If the Cubs choose to go down that road again with the best players on their roster and those players say no, then it is incumbent on the front office to explore trading anyone that does not want to make that same commitment and chooses to get to free agency.
With only two years of control left on Bryant, Rizzo, Baez and Schwarber and three on catcher Willson Contreras, the Cubs are at a crossroads for their future.
If they decide to ride it out with their stars and hope to re-sign them when they reach free agency, then the Cubs run the risk of turning into the Detroit Tigers. They had a 2014 starting rotation of Justin Verlander, Max Scherzer, David Price, Rick Porcello and Anibal Sanchez. All five men helped win a World Series ring, but all five men did it for a franchise other than the Tigers who got very little in return after losing those stars.
Epstein has a responsibility to maximize his assets and to try to extend the Cubs window of contention as long as he can. The only way to do that is to either lock up his stars now or move them for as much as he can get to replenish the talent level in the organization. Despite many clamoring for the Cubs to throw more money at their holes and trying to sign the best players on the free-agent market, I fully expect Epstein to pull back from that path which is often fraught with peril.
Take your heart out of the equation and ask yourself what you would do if you were in Theo Epstein's shoes. The answer is clear and obvious. Maximize your assets. It may hurt to see a big name in another uniform, but it is the only way to keep the Cubs a contender for years to come.