1. Looking to the bargain bin when building out a bullpen
Look. This is a strategy that's worked extremely well for the Cubs in recent years and, if we're being honest, the last month has been much stronger for the bullpen - and that includes Michael Fulmer, who put up a 0.66 ERA in the month of June. But it's clear the front office could've brought in more proven commodities and addressed the lack of left-handed depth, both of which could have prevented the early season woes in the later innings.
On the year, it's been a very middle-of-the-pack showing for Chicago relievers - but Mark Leiter, Adbert Alzolay and Julian Merryweather have emerged as quality options for Ross as the year has progressed. There's been a glaring need for left-handed options since Opening Day and the latest injury update on Brandon Hughes makes it clear that need is as pressing as ever.
I'm not saying the solution is going out there and paying top-shelf money for ninth-inning guys. But there were established options available last winter and, instead of opening up the pocket book, Hoyer and Hawkins went with Fulmer and Brad Boxberger, who was ineffective and has been injured now since mid-May.