It was a low risk, decent upside play.
And frankly, I'm still not convinced it wasn't a savvy signing. We literally haven't seen Dobnak healthy for a decent stretch since that time - which sucks but can happen to any pitcher - and I still think he's a capable pitcher if he can ever get healthy.
And Randy is an eminently likable character with a fantastic story. If, at the end of a few years, the Twins essentially donated a few million dollars to him, all I can say is "cool".