I think the Trophy feature is a way of showing sportsmanship , it reminds me of what footballers do after a contest when they exchange kits.
When to give trophies and why

I think the second place ribbon is a great one. I've given that one to someone who was rude in chat.
i like that idea will use it

They are Facebook-esque "Free Gifts" are they not? I mean, a lot of them don't really seem to have *anything* to do with chess games.
"Enjoy a Taco" ?
Sometimes, I use them (or have them used on me) almost as a form of trash talk. A friend (who definitely isn't a mentor/coach of mine) once sent me a "Great Student!" trophy and wrote a note on it about "many hard lessons to come."
Most of my friends are jerks, incidentally.

Trophies are meant to be given to everyone (winner and losers) to aknowlegde to the other player that it was a good or enjoyable game to play. Also, the trophies are not all geared around the winners (Good Game, Good Sportsmanship, Fishy Play, Novelty Alert, Strikiningly Strong Play, I Want a Rematch, Mental Relaxation, Great Defence, Strong Fortress, Exhausting Game, Moving Up, Game Imprint, a-MAZE-ing, Inventive Game, Surprise Ending, Small Difference, and Chance) are all trophies that don't have to be given to the winner.
ADK

In have a gazillion good sportsmanship trophies, all of them for resigning lost games. I never know how to respond to them. I don't really get by what standards sportsmanship is measured. Ah well, if you ever get a trophy from me, you can feel really special, I don't give many.

Giving out trophies to deserving opponents is the right thing to do. It is my way of showing appreciation to their ubber good chess skills, or simply put, ubber good sportsmanship.

well I give out my trophies win or lose in a online turnbased game just because you have so long to look at it that that errors should be few. Live chess you would have to make an incredible comback or just flat out destroy me to get a trophy.

Remind me never to play a game with you, Snakesbelly!
I give trophies when something does something surprising, resourceful or particularly helpful or friendly.
I give a trophy to anyone that put up a fight till the end, whether I won os lost. If it was a GREAT chess match, I give them a "Good Game" trophy. I also give people trophys for giving me great advice, and other such things. I have only given out 7 trophys though, I am sure to pcik the right people.
I think we should have a maximum number of trophys you can give out in a period if you ask me, maybe that will make people more selective.
I agree 100%.

The trophies are actually a lingering bug from chess.com.v1 that didn't get worked out in chess.com.v2. True story.
Well the point is quite valid. The name "TROPHIY" should be replaced by some other appropriate name like, "AN AUTOMATED SHORT MESSAGE"