2 words : Player Development.
It's what has haunt this organization since Reinsdorf took over.
The trades were 100% the right moves. And even the half ass free agency work to supplement talent has been OK. Not great, but OK. But it's those second tier accessory prospects that have doomed this team. Too have not found one single guy to contribute from the list of : Adolfo, Basabe, Gonzalez, Rutherford, Walker (traded but sucks), Burdi, Hansen, Stiever, Collins, Madrigal (traded but sucks)
By finding zero contribution from that mid tier is how you end up with a payroll at $180 million full of s%*#. Over-paying for relievers. Trading for washed up corner OFs like Pollock. And most likely ending up with more washed up over-paid garbage like Gallo/Bellinger this offseason.