There are some true elements to it, though it's a bit stark for my taste. For one thing, they are trending in different directions: the Pirates have a whole host of problems, whereas the Brewers are more positioned in terms of on the cusp of earlier than expected success. As a retroactive critique of what the Pirates did over an earlier period, I buy into the idea, and perhaps even moreso than from the perspective of today, since the Cubs weren't quite yet a force until the 98-win season.
From today's perspective, I think there are different ways to look at it. On the one hand, I think with Cole, you had to turn him into more controllable assets. To me, the biggest and really only question there is whether his value would be higher at the trade deadline than it is now. I lean towards no, and I think this was the biggest reason why the move came now.
With Cutch, it's a bit different of a story. Certainly the blow will be easier if Reynolds ends up as an everyday player in 2-3 years, but I think that's where you could take the perspective of presend-day talent and the weaker market and say the Pirates should have made a more decisive attempt to win. Let Cutch play things out in a contract year, take the comp pick, and move on. Supplement him with some actual talent: we could easily have made all these same moves as depth/4th OF types, and then spent hardly anything to get another infield option, and invested in one of the starting pitchers.
How much does that all really move the needle? I'm skeptical, but it's at least more viable, and certainly a real decision to compete, much moreso than what we've gotten from Huntington, which is the baseball equivalent of thoughts and prayers.