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One of our Chicago Skimrish Wargames club members decided to organize a secret Santa game over the holidays. Pretty standard procedure: pick a name, paint a model for that person and exchange present at a club meeting in January. 6 Members participated and the results were pretty impressive. Every member went above and beyond finding rare figures and/or doing conversions to create something the recipient would appreciate and would fit their interests. Here's the awesome pre-30k Rogue Trader era marine that I received:

and an amazing standard bearer painted by one of our other members

My buddy who organized the game wrote it up as a blog post and you can see the other 4 great gifts and a picture of me looking a bit too enthusiastic here:
http://chicagoskirmish.blogspot.com/2015/01/csw-annual-gift-exchange.html
The group who signed up for this are pretty reliable folks so I knew they would deliver, but I didn't realize everyone would be so thoughtful and put so much effort in. This will not be the last time we do this.

Have any other groups tried something like this? How did it go?

Oddly I am working on something similar to this.

Originally I did the Dakka Secret Santa this year which was a lot of fun. I also, although it was late notice, tried to organize one for the local NW group. However no one really showed interest except for someone who suggested something similar to what you did, a hero swap.

We agreed we would each paint up someone from WH40K then do an exchange. Even though Christmas is over with, we are still doing it so we can share with the group and hopefully do something similar next year.

I didn't even know there was a Dakka secret santa!

Best of luck with your group's exchange.

Yeah I didn't know about it until I mentioned it another thread about how a secret santa exchange would be interesting. I was directed to the DCM section where it usually is located. Essentially someone is the main moderator for it collecting the lists, assigns out secret santas. Then the participants sends out 200g or more of bits (without sprue) as gifts. That is the minimum rule although usually it is more and sometimes isn't just bits, but painted miniatures, full sets, NIB, etc. It was a really fun experience which I would definitely end up doing again.

Sounds like fun.

I just took my turn in a traveling bits box over at Lead Adventure. Sort of a take-and-add box. Though everyone seems to go beyond and give more than they take. Was a good experience and I got some cool stuff out of it.