I think the idea was that "putting fans in the seats" would equate to winning more games. The Pablo signing did just the opposite.
Looking back, signing Scherzer instead of Pablo & HRam was the best move, but some context is needed. At the time, we needed offense and pitching. The long list of top FA pitchers (like Price) coming onto the market the following year was at least a reason to think of the 2 year plan as build offense one year and pitching the next.
Ultimately, the GM gets the blame in hindsight. Porcello and HRam sucked during Ben's last year, then did very well to great DD's first year in control, and we win the division. Much of being a GM is rolling the dice, and Ben deserves the criticism he gets for several bad choices, but he also made some good moves, like Porcello and farm building, even though he was not directly benefited by them.
I'm glad we had Theo, Ben and now DD. I'm happy with all 3.