Fans of contending teams eventually come to rue some of the prospects their club traded away in pursuit of the championship they all desperately wanted. But all contending teams do it. The dynamic of win-now teams dealing with win-later teams is pretty much how parity exists in 21st-century baseball.
The Chicago Cubs have been no different, not in how they built up their talent pipeline, nor in how they leveraged that talent into a pretty wide window of contention. But there is often a crossroads moment that arrives for even a smartly built team, and the Cubs could be facing it. Chicago still has reasonable hopes for another playoff run in 2019, but there is also a disaster scenario that a shaky start might portend, one in which the pitching staff crumbles at the same time the front office lacks the payroll flexibility to patch it back together.
By most accounts, the Cubs' minor league pipeline has largely been emptied through attrition and trades the past few years. Chicago's system entered the season ranked No. 29 by Baseball America, one spot better than that of the defending champion Boston Red Sox, a club that currently can empathize with the Cubs' plight. Like Chicago, Boston emptied its once-fertile system in service of the present.
But what if they had not?
