Maybe we're missing some side info, but I'm a bit confused about why you suspect the boss is playing some kind of passive-aggressive power-trip game with you.

What's the quote - "Never ascribe to malice that which can be explained by stupidity"? That probably applies here.

IMO, it's bad form to assume the boss is purposely jacking you around, when he/she may very well just be clueless about optimal flight selection (as most people are).

That's probably not a healthy way to begin the new boss-employee relationship, even if you're keeping those thoughts to yourself.

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BTW, I *also* hate when other people book my travel. It gets messed up at least 25% of the time, and it is rarely optimal.