Chicago Cubs: “Just pretend it’s flat ground!”
The Cubs probably shouldn’t have signed Tyler Chatwood, Brandon Morrow, or even Craig Kimbrel. I don’t know who the alternatives would have been at the time offhand, but those three didn’t work out very well. To be fair, even at the time each was signed, they were all pretty serious gambles due to injury history or previous ineffectiveness.
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The Cubs also should have signed a deal with Comcast, NBC Sports, or whatever conglomerate would have given the team hundreds of millions of dollars without any start-up costs. Sure, the club could have made more money going their own route in the best of all scenarios, but anyone could see the way cable was heading. Starting up your own channel and dealing with carriage concerns was enough of of an undertaking to question its viability and fiscal return. Then the pandemic hit and now Marquee already looks like as big of a flop as, well… the Titanic.
I realize that no one had any idea the pandemic was about to hit and upend everyone and every business in this country, but being a little less greedy probably would have served everyone a little bit better in hindsight.
Then again, there are probably a lot of things everyone would have done differently, both in their personal and professional lives, given what we know now.