I think it's certainly fair to criticize this front office's complete inability to extend any of their core position player prior to free agency. All of Vlad, Bo, Chapman and Semien were guys in my view who were worthwhile in investing in to sustain a long term position player core. I can't help but wonder if the front office was lowballing these guys to a certain degree, or if it's a case where all of these players were essentially looking for free agency level mega deals to sign on the dotted line.
The Vlad situation reminds me a little of the Edwin situation years ago. The front office was largely painted as the villain despite Edwin and his agent turning down the best offer they received that year in free agency and being forced to take a shorter deal as a result. I think the Vlad situation is another unfortunate situation where it's kind of hard to fully blame either side. It appears as though Vlad has been insisting all along on being handed a contract that he hadn't fully earned, and the front office was looking to share a bit of the risk of an extension in the case where Vlad never became a consistently elite offensive contributor. I'm nearing the point where if the team can't agree to contract terms with Vlad it might finally be time to ship him out to another organization and consider a full on rebuild.