With two DUIs, you should have an attorney and hopefully the same attorney for both. Listen to your attorney. Good luck.
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I have seen this situation several times. What matters is if the San Francisco DA knows about the second case. If not, settle the San Francisco case ASAP (tomorrow - advance it) and then deal with the felony. Perhaps the felony can even be reduced to a misdemeanor if the San Mateo DA does not know about the first case. If the San Mateo DA does not know about the first case, the second DUI might even be resolved on first time DUI terms.
If both DA's know about both cases, I resolve the misdemeanor first and the felony second, but in such a case it would be impossible to resolve the second case as a first-time, misdemeanor DUI.
Which case to resolve depends entirely on what each prosecuting agency knows. Prior to the filing of each complaint, the prosecuting agency runs your record or what is commonly referred to as your RAP SHEET. Your rap sheet would contain information that would indicate how many felony and misdemeanor bookings you have had, and provide an update as to each one. I have worked on cases where one client has two pending charges in both the same county, as well as different counties. Which case to resolve is entirely strategic on your part. You should know that by pleading guilty to Felony DUI, any FUTURE drunk driving charges (even simple and basic ones where people are not hurt - still are considered felonies) because you have a prior DUI).
In this case, I would recommend hiring a competent lawyer to assess which prosecuting agency is less likely to review your record before finalizing any deal. Some prosecuting agencies are so busy with pending cases that they don't have the time and resources to double check your prior driving record and criminal history prior to concluding cases. While your second conviction would tend to be aggravated by your prior DUI, I think you can try to settle both cases possibly on the same day or within a few days of one another. It's entirely possible that for purposes of sentencing, both would be considered first time DUIs. However, in the future, if you get another DUI, the new one could be considered your third.
I hope you don't have a public defender assisting you in both of these cases. I am not saying that public defenders are not skilled enough to handle your case. I am suggesting that this type of situation you are in requires finesse and strategy. The same attorney must resolve both cases quickly and efficiently.
Mr. Cernyar is correct. If you have an attorney talk with them as they are in a better position to know your facts and sitiuation. If you do not have one, you should contact one in your area for assistance. If you want to find one in your area here on AVVO you can select "Find a Lawyer" at the top of the page. Good luck.
If DA doesn't know about the other because they are in different counties, why not arrarrange them so they resolve on the same day. In most counties, you can do what is called a "977 plea through counsel" on a misdemeanor.
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This questions is too complicated for anyone to provide a certain answer. This is a question for your attorney.
If possible, the best option is often to resolve them on the same day, but it's entirely dependent upon the facts of your case.
With a skilled attorney that has handled resolving multiple simultaneous DUIs, you will be able to get through this situation.
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