A lawyer would need to know the facts of the cases and you in order to answer. Your lawyer is in the best position to answer your question.
I am a former federal and State prosecutor and have been handling criminal defense and personal injury cases for over 21 years. The above answer, and any follow up comments or emails, is for informational purposes only and not meant as legal advice.
Impossible to answer without knowing the facts. If your first is still pending it may be possible for your attorney to work out a disposition that covers both cases. But the fact that you picked up a second in less than a year will make any sort of disposition that doesn't include at least some probation or possibly jail difficult without some significant pro-defense issues.
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Depends on the facts and other factors. You need to obtain representation from an experienced DWI defense attorney sooner rather than later. No “general” answer on this one.
You are at risk of going to jail but it might be avoidable. You should attempt reduce the risk of going to jail by retaining a lawyer who limits his or practice to handling DWI cases to represent you in both cases. You should also seek out immediate help for your obvious drinking problem. You can not afford to ever get a third DWI.
The information provided is not intended to be legal advice, but merely conveys general information related to legal issues commonly encountered. The information is not guaranteed to be correct, complete, or current. I make no warranty, expressed or implied, about the accuracy or reliability of the information. You should not act or rely on any information at above without seeking the advice of an attorney. The determination of whether you need legal services and your choice of a lawyer are very important matters that should not be based on websites or advertisement
This is difficult to answer in a fact-vacuum, but I believe the only reliable answer we can give is that it is certainly possible. You absolutely need to consult with an attorney asap and see if there are any grounds, procedural and/or substantive, to attack either of these cases (or both). If you're able to re-ask your question, you'll want to include which VTL charges you face (misdemeanor, felony) as well as any accompanying charges (suspended license, reckless driving, etc). Even still, nothing can substitute for the targeted advice of a lawyer who is able to review your file and give an opinion based on the specific facts in your cases.
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