There is not enough information given to be able to accurately answer this question. The short answer is that jail time is a possibility for any probation violation.
If he violated probation two times and the bail is that high you should spend the money on a a good lawyer to try to get the lowest sentence and best possible disposition.
The short answer is yes. Anytime someone is already on probation any violations of the terms of that probation open the person to a potential jail sentence up to the maximum allowed for the original charge that they are on probation for.
A second probation violation will probably result in time in jail or prison. As to how much time, that depends on the person's criminal record, and the judge.
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