The context matters here - Jed clearly attempted to compete pretty much right away by handing out contracts to Taillon, Swanson, Suzuki, and so on. So he has to be measured as a GM who's tried to build a contender for 5 seasons. If he came out like Theo did and said that we'd have a couple of difficult seasons to build up the farm, the analysis would be different. Why should he get the benefit of the doubt when he's handed out bad contract after bad contract?
The moment he signed Swanson, Suzuki, Taillon etc. the message was clear: we are trying to win. I just think they made these moves too soon with where the org was at the time.