For context, I work at the in-house bank of a pretty successful local car dealership, and the department head in question runs two Buy-Here-Pay-Here lots along with the bank which I work for that finances all of the deals for said BHPH lots.
Granted, he is a pretty nice guy. Easy to work with, pretty smart and practical, and I like working with him quite a bit. He's genuinely a good dude to work for, so I can understand people wanting to get him something nice come Christmas.
I was in a bit of a financial bind at the time, my wife was student teaching to finish her degree, which is an unpaid internship. We were able to borrow enough from a 3rd-party student loan company to cover her half of the bills while she worked almost 60 hours a week between meetings, lesson planning, grading, etc. literally for free, but the rest of the expenses including gas for our cars, groceries, food, etc. fell on me. Which was fine, we made it, but it was a struggle for sure.
Cue early December when my boss comes in and announces that we're all chipping in to get the big boss a new phone for Christmas since his just broke. They were only asking for $20, but when I flat out said I couldn't afford it in front of everyone, half of them (including my boss) looked at me like I had set their beloved family dogs on fire in front of them. A couple co workers were in similar situations as me so they sympathized, but of course didn't say anything out loud like I did to avoid similar treatment.
Look, it's only $20. Sure. I get it. But this is for our department head that I happen to know makes a hell of a lot more money than the rest of us. He invited me and a couple sales guys out to lunch over the summer when the stores were all well, and paid for our lunch, which was great. Super nice of him. During this lunch he revealed that between what he was making at the stores, what he had in savings, and his investments, I believe he's a LandChad for either a small apartment building or a couple duplexes, he's worth over a million dollars on paper.
Over a million dollars. So needless to say, he's killing it financially. He's an older guy, maybe not super close to retirement, but he can sure as hell afford to buy his own new cell phone. I wasn't sure whether or not to post this here or on AITA, but why on earth should I be obligated to give this guy that has more money than I possibly might ever have in my life $20 when I am legitimately struggling to put food on my own table?
It left a really sour taste in my mouth. Still with the company and my transgressions have since been swept under the rug, but I know to expect something similar next year. The year prior, we all pitched in and got him a brand new set of golf clubs. I had just recently started so I begrudgingly gave up the money without saying anything, but I'd become a little more tenured at the time of the refusal so I was more comfortable speaking my mind at that point.
This also isn't the first time I've experienced something like an office pool to get the boss a nice gift. Why are the people who make way less obligated to get the person who makes way more a gift? Shouldn't it be the other way around?