But Tuesday, 58-year-old Charlotte DePersia is likely to learn she's used her last get out of jail free card.
"I couldn't imagine that she was not going to be drinking again," Suffolk County District Attorney Thomas Spota said.
It was over Suffolk DA Thomas Spota's strenuous objection that Supreme Court Judge William Condon allowed DePersia to walk with a slap on the wrist after her most recent escapade.
Back in November 2010, she was guzzling a Starbucks cup full of red wine as swerved along a darkened Montauk Highway in Bridgehampton. That's when she slammed into an SUV with four people inside, including a pregnant woman and Lindsay Soyka, who suffered multiple broken bones.
"Does she need to kill somebody at this point? She's already had three offenses, she's hurt four people. What's next?" Soyka said back in July 2011.
Last summer, DePersia pleaded guilty to DWI and vehicular assault, but convinced the judge she'd sobered up in rehab.
He let her walk with community service and five years probation, including a loss of driving privileges and an outright ban on drinking.
But Tuesday, DePersia will be back before Judge Condon, after probation officers say she violated the terms and drank anyway.
"I just could not understand why the judge was giving her yet another opportunity for treatment when she has clearly shown that she's a danger," Spota said.
This could be Charlotte DePersia's last day of freedom for a while.
Tuesday, she'll walk back into a Suffolk County courtroom where prosecutors hope that same judge says enough is enough and sends her to prison for up to four years.
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