Chicago Cubs: Five trades that could have created a dynasty

While it’s impossible to predict the future, here are five trades from the past which could have made the Cubs the dynasty we all thought they would be.

They say hindsight is 20/20. Given that the year now reads 2020, it’s apropos that we take a little gander back in time to investigate five potential trades that could have made the Cubs into the veritable dynasty we all expected them to be after the parade in November 2016. Granted, all of them would and could not have occurred in this alternate timeline, but each and every one of them would have been feasible and plausible at the specified time.

While this is an exercise in futility and tomfoolery, the fact remains that trades have the potential to happen at any time and for any reason. It also stands to reason that since these were all players who were traded at one point, the Cubs could have been players either at that point or another. Also, trades that were once thought foolish at the time they were made now look stupendous, and the inverse also holds true – that’s just the nature of trading.

Sometimes, trades are efficient and productive for both teams, as in the case of the Gleyber Torres for Aroldis Chapman deal that gave both teams exactly what they were looking for knowing all the risks and future ramifications. Cubs fans may look back on it and say they should have given up Addison Russell instead of Torres, but they probably wouldn’t have won a ring without the services of Russell at shortstop in that miraculous postseason run. Sure, it was a lot to give up at the time and in hindsight, but would any Cubs fan give up their 2016 revelries for Torres back now? Don’t answer that – there are plenty of curmudgeons out there.

A sure thing is better than a gamble in the business world and professional sports, but gambling can often be more fun and exciting – and isn’t that what a lot of trades are at their core? In that vein, here’s a look at five prospective deals from seasons past – each of which could have extended the Cubs “window of opportunity”/playoff run and created a true Cubs dynasty.