No doubt, and when one superficially looks at the rotation he inherited vs the one he left, it's easy to label that part of his judgement "clueless-" the low ball offer to Lester being the lowest of the lows, however, the staff was all nearing free agency and coming off "beergate."
Serious mistakes and blunders were made. I'm not defending Ben's choices on starting pitchers. I hated the Masterson deal, but I liked the Miley deal. I disliked the Dempster deal, but many thought it was a good one. I hated how we treated the Lester negotiation, but once we screwed that up, I felt the trades (staff dump) we made was called for. I had hoped we'd have traded those guys for younger players, but Cespedes did bring us Porcello and Kelly is now blossoming into a quality set-up man. Craig bombed out, of course, but that was hard to know was coming. Peavy brought us Hembree. We got Marco Hernandez for Doubront. The jury still out a little bit on some of our acquired players, but the years of team control we had remaining of the starters we traded away were minimal.
At the time, I argued we should have signed Scherzer over HRam & Pablo, but understood the plan to wait for the stocked free agent class of the following year. Ultimately, it's Ben's fault hardly anybody performed like they had the year before being signed or acquired (HRam, Pablo & Porcello being the most notable), but he wasn't clueless, IMO.
I firmly believe he'd have made a trade or two like the Sale one but not trades like Kimbrel. He'd have spent as large as DD was allowed but maybe not on Price, which probably would have been a good thing. Maybe he doesn't sign Young or Moreland. Maybe he doesn't trade Travis Shaw (cheaper than Moreland's contract). Too many maybes to know anything, but I doubt Ben was going to just keep stock-piling prospects for the sake of it.