I do not practice in KY. This, however, is a common situation.
A person on probation commits a new crime. So now he has two problems: the new crime and the likely violation of probation. Once he pleads guilty on the new crime, i.e. is convicted of a new crime, he has violated his probation based on that new conviction. He faces sentencing on both. Separately.
Sometimes the plea deal on the new crime is officially packaged with the old crime/probation. For instance, all parties and all judges agree prior to any plea that he will face concurrent time or, perhaps, more time on the violation of probation. If this agreement is not in place, then he can face up to the maximum on the probation violation.
Typically, in the same county, the prosecutor's office is the same and this sort of resolution is a possibility, even if the judges presiding over the different cases are different and have different jurisdictions. But often such a deal is clarified on the record prior to the plea on the new crime.
Sometimes either the prosecutor or one of the judges does not think the defendant should get such a deal. In those situations, sometimes the defendant, such as your friend, gets a relatively lenient sentence on the new charge, while getting substantial time on the probation violation for a lesser offense. This is not an uncommon outcome when a person is on probation for a DUI and then gets convicted of another one. Actually, it's probably still a better deal, overall, than if he got the max on the new crime. He should expect that his new probation will be more restrictive and more intensive than his previous supervision. It is now clear that your friend has a serious drinking problem that will need to be addressed.
As to your desperation, if you are the person with whom he was about to start a family, you should consider what you need to do to support yourself financially and otherwise while he is doing whatever he needs to be doing. You may want to get a better job, or get trained so that you can get a better job. You need to be able to rely on yourself, as he may be unavailable for periods of time. Think about how to improve your lot in life, with or without him. Desperation is pointless; start making your plans for yourself. Think about yourself as becoming the strong person in the relationship for now.
DISCLAIMER: I do not practice in your state. This answer to a short question is provided solely for general informational purposes and based on general legal principles and court practice, both of which differ from state to state, even from judge to judge. This answer does NOT constitute legal advice, create an attorney-client relationship, or constitute attorney advertising.
Yes, but I would check to make sure there was not some sort of mistake made. If this was his 3rd DUI and plead guilty, then yes that would violate probation for his 2nd DUI goes. Whatever judge imakes decisions. Judges take vacations, get sick, get stuck in long trials, etc and other judges substitute, just like teachers. The substitute judge has all the powers and responsibilities of the regular judge. Sometimes the substitute judge will do whatever he/she wants and sometimes the substitute judge will try not to interfere with the regular judges decisions. In you cannot afford attorney contact KY Dept. of Public Advocacy for low cost or free attorney. Thank you, please click on the website, "In your corner."