I think Bogey could have gotten more. It was clearly a team friendly deal.
All Bogey got was one extra year of guaranteed money, but it was at a rate that even at the time, was an underpayment. While true, nobody can predict the market and inflationary aspects, but Bogey would have made more had he not signed that deal.
One could argue, he'd have made less, in the long run, because he'd have been a FA after 2021 not 2022, and he'd never have gotten this deal with SD after 2021, but that is not really related to judging the contract he signed.
In hindsight, I wish DD would have kept negotiating to try and not have the opt out, but we don't know what Bogey would have taken. Would he have accepted $23M x 6 with no opt out? $25 x 6? It's hard to blame DD for something we'll never know, and that's kind of how I feel about what happened with Bloom and Bogey. Without knowing the bottom line dollar and years amount Bogey would have accepted, it's hard for me to fault not signing him. That doesn't lessen the fact that the $30M/1 yr offer was a slap in the face, but this does not take away from the main issue: what could we have gotten Bogey for 2 years ago, 1 year ago, 10 months ago or even 3-4 months ago?
I think he knew he was going to get a big payday, and the Sox would not be the team offering it.