First I'd like to say I'm all for capitalism and believe private companies should do the best for its owners or share holders.
However, companies in the service industry (including airlines) should take care of their most loyal costumers. I have been a Delta Medallion for almost two decades. I was there when they were struggling in the verge of bankruptcy, and I chose to spend hundreds of dollars more in Delta tickets (versus other airlines) because I wanted the excellent costumer service and medallion perks.
All that said, today I was checking in for the short DCA-JFK flight and got this message:
I would not pay $89 for such a short flight. Furthermore, I had checked the seat map before and notice several open first class seats. Right after check in I opened the upgrade list and sure enough I was number one on the list with 5 seats open! I'll get the upgrade for free, but it's been a long time since as a Platinum Medallion I got the upgrade cleared 5 days before departure as Delta advertises on their Medallion benefits page, see below:
The lesson here is: Make sure to check how many first class seats are open before you check in. And if you get the offer and feel like paying what Delta asks you, by all means do it! But remember that as a loyal Medallion Member you should be getting that seat for free.