The soul of the bet was simple "conviction" by Sept. 30.Pretrial supervision conditions are issued early on - and before the plea - so your point on this one misses the mark. Your best argument is that there's no conviction until the plea is certified. But even then, the timing of how this all could work makes the bet too vague. It was possible that he could have plead and been sentenced on the same day. It was also possible that he could plead and then be sentenced several months later. Neither of you anticipated any of this in the original bet, I'm sure. In fact, I don't expect either of you anticipated a plea at all.
In regular jargon, Surfdog probaby wins this bet because a plea is generally considered a conviction. In technical jargon, you probably win the bet because a conviction needs to formalized on the record. In reality, neither of you win the bet because there's no way to tell what you intended regarding a plea.
I had no idea there would be guilty pleas in this ordeal. I thought once charges were brought, they would go to trial.
But that didn't happen when he plead guilty. He didn't plead the 5th or not guilty.
And, this whole investigation is far from over with Clinesmith's sentencing now done.
I expect more charges in the coming weeks/months. Covid is slowing this whole process, like everything else, unfortunately.
They even had to do this whole charge/conviction/sentencing ordeal remotely with tele-com.