The New York Times Magazine runs an "Ethicist" column that's essentially an advice column for ethical dilemmas. A couple of months ago, the featured letter was from somebody who had received a valuable diamond ring from a much wealthier relative, asking whether it was ethical to sell the family heirloom for needed money (
link -- paywalled for
New York Times subscribers only). The columnist's answer was that a gift is a gift, and the recipient has the right to do with the gift what they please... although in order to avoid strain on family relationships, it would be courteous to inform the gift-giver about the decision to sell the ring and why.
I scrolled through the most upvoted reader responses in the comments section and saw that a majority of readers recommended other courses of action, although those opinions were largely in the context of the ring's sentimental value as a family heirloom (among the most popular suggestions: see whether anyone else in the family would want to purchase it (although still expect hard feelings) or sell the diamond and replace it with cubic zirconia or a similar lookalike).
It's clear the iPhone held little sentimental value to Roger or anybody in his family, so there was no priceless value to consider. Looking at it from the gift-giver's perspective, if I gave somebody a valuable gift only to find out that they later sold it, while I would recognize their right to do that, it would certainly make me less inclined to give them any other gifts in the future. But I don't think Roger's going to be worried about those ramifications.
Using the celebrity connection to try to goose the selling price is a bit low... although I'm guessing Roger has no qualms about profiting off the name of the man he attributes to his firing. (Even though I assume the buyer was only interested in "first-edition iPhone in original, unopened packaging" as opposed to "iPhone Drew Carey gave some guy.") But with no sentimental value to consider, what reason is there at this point to hang on to an outdated piece of technology that will never be used?
To add an additional perspective: this memory is roughly 15 years old, so I'm sure I'm getting some of the specifics wrong, but I remember Drew once telling a
TPIR audience about the time ABC gave him a luxury car to celebrate the success of
The Drew Carey Show. He didn't need the car, so he gave it to one of the sitcom's production assistants. And I'm pretty sure the story ended with the production assistant selling the car (because you can't afford the insurance on a luxury car on a PA's salary). Drew didn't appear particularly offended by the PA's decision to sell the car.