You can't expect a GM to win rings with a spending budget of $60-80M. He did a great job with what he was given. To say he was "hardly successful is a gross understatement. One could argue he did better than anyone in MLB within the context of the budgets and situations handed to him.
Sure, he still needs to prove himself, here. Dan D. had the same reputation coming to us from Montreal, and he never won a ring, but he did set Theo up nicely.
I'm having a hard time understanding all the gloom and doom on Henry on Bloom. I get the sadness of losing Betts, and maybe some here never had to endure decades of frustration following the Sox of old, but I'm damn proud of this team and the owners and managers. We've hit a bump in the road. We all knew it was coming, or should have, and now it's time to look forward to a swift rebuild and return to the top. The quicker the better, for us fans, but we need to be more thoughtful about the long term, so maybe this doesn't happen so often.