What you were expecting to happen, and what actually happened:
I was expecting some gain in gold and buff to Quickpaw Jack’s damage. This did not happen in any match out of 10. One of those matches was against a 4x Gold Ring team, in which I allowed the first enemy to cast, and then cast with Quickpaw Jack. Zero gold gained.
How often does this happen? When did it begin happening?
Every match where quickpaw jack is used.
Steps to make it happen again
Play with Quickpaw jack on the team, and cast his spell. (Whether against an enemy known to have gold or not)