What if the Cubs had stopped making trades in 2016?

Fans of all 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 crossroad 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…