I'm a bit different than enscheff on the extension arguments, but I've always written that it isn't the individual extensions that are the problem. For the most part, they are reasonable and below market for a number of guys. Olson likes to play for the hometown squad, but he could have probably scored a $30 MM AAV if he had left after 2023.
The problem for me has always been the totality of the extensions. I just don't think Anthopoulos and company thought things through enough and were more selective in who they chose to extend. Buying out Harris' arbitration years made total sense, but should they have gone beyond it? Strider already had TJS. Given that he's a bit undersized and has a high-effort delivery, did his extension make sense. Pitching is the one category where the player development team seems to doing exemplary work and the depth was moving up. I suppose they had questions about Baldwin, so they extended Murphy beyond what really makes sense. I know the front office analyzes things to the nth degree, but I think they could have used better judgement when making some of these decisions.