I agree with the theory that dude has put forth that the Orioles didn't really bid against themselves, at least not substantially more than a small amount to get the deal done. Rather they restructured the offer so that on the surface it seemed much bigger (for Davis and Boras' sake) by deferring a nearly unprecedented amount of money, this kept the value of the contract the same even if the raw dollar figures were much higher. I forget the reports from the time but 6/$144M seems to stick in my memory, was that the original Orioles offer or just a deal that equates to the same contract Davis actually got (they are nearly identical NPV)?
Also 98% of Orioles fans everywhere would've signed Davis to say a straight 5/$115M deal. People are gonna have to show me posts from 2016 to get me to believe they would've turned something like that down (I know there are a few, but not many). Is it really dramatically different that he got 7/$161M with a ton deferred? So much so that your idea was smart and the Orioles idea is the stupidest thing in the history of baseball? Yes it's a larger scale, no doubt, but Davis went south so fast that no matter what the contract was it'd be laughed about as one of the worst in baseball history even if it was a bargain when he signed it. The major difference between Pablo Sandoval and Chris Davis is not the extra 50% or so on the contract, but it's the impact that the contract had on the franchise. The Red Sox shrugged it off as nearly no issue at all. The Orioles have spiraled downwards and are cutting costs at every turn.
I appreciate the thoughtful breakdown of how you remember the negotiations unfolding. But there's one thing that can't be explained away. The O's offered X, he signed for more than that original offer. That is the definition of bidding against yourself.
Here's what I remember about that process. The O's made an offer. Boras said that won't get it done, because other "teams" have shown great interest in Davis's services. Some time passed, and Boras started talking about how Davis wasn't just a 1Bman, that he's a a skilled COFer as well. This is when the rumors started floating that Detroit (who already had a guy for 1B) were interested in that COF idea. None of that "multiple teams interest" propaganda has ever been substantiated. Eventually, Duquette makes the statement that the O's made an offer, and that offer has an expiration date, because they can't hold up their entire off season, waiting for one player to make his decision. More time passes, and Jim Duquette (as a regular on the XM MLB channel, says Dan is tired of waiting for Davis, but he's been told that money is for Davis, and Davis alone. It cannot be used to sign a marquee pitcher (which is what Dan wanted to do). Eventually Dan is no longer involved in the Davis negotiation, because Peter took over the entire thing.
So, not only did they actually bid against themselves, by upping their original offer (even if it was only a marginal increase), they failed at negotiations 101. The stalling was Boras desperately trying to get other teams involved. A smart baseball mind would have pulled the offer, wait for Boras to come back to accept, then let him know the new offer is X number of dollars less.
And while I wasn't here during those negotiations, I can tell you that I vehemently opposed retaining Davis at a market value rate, because he was too streaky of a hitter. His usual season involved a few, two week stretches, where he'd carry the team, followed by several week stretches where his bat disappeared. I posted this on the SunSpot board. Davis at $10M is fine, Davis at $25M will frustrate you, because he'll ultimately end the season with his usual production. But there will be a lot of 2-1 losses that could have been wins, had he been a more consistent hitter.