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What were you doing in the ’90s that might come back to bite you in the a**? During the mid-90s, Tiffany Webb was trying to get her foot in the door as a model and in the process of doing so, took some alluring lingerie-clad photos when she was between the ages of 18-20. But by the mid-90s, Webb decided to leave that all behind to become a teacher  for the city of New York (which she finally did in 1999), and in the hopes of having a clean slate, she not only tried to have the photos taken offline but she informed her employers of her former days as a lingerie model when first hired. Though she has had a successful career, since that time, those photos have haunted Webb, circulating around the Internet on less than tasteful websites, and causing her to be investigated more than once by the Department of Education when the photos surfaced. Each time though (a whopping three investigations), she was given the green light to continue working.

Now 37, a guidance counselor at Murry Bergtraum HS for Business Careers, and after working for the Department of Education for 12 years, Webb was recently fired after a student brought the pictures (which are heavily Photoshopped) to the attention of the former principal. Coincidentally though, Webb was fired last December as she was just days away from being a tenured guidance counselor and was to sit very pretty with an $84,000 per year salary. According to the chancellor’s committee, her conduct was “unbecoming” as an employee. They found that the fact that students could easily access her scandalous photos was unacceptable, and questioned what kind of role model she could be with the photos running around online for all to see.

A 2-1 vote, according to the New York Post is what got Webb the boot, and the one nay vote said, “Her professional work as a guidance counselor has been outstanding, and she should not be punished for something that happened years ago.” Unfortunately, everyone else didn’t see it that way, so now, Webb, who has changed her name and taken a position in New Jersey, is suing the DOE, charging wrongful termination and more. The young woman, who was very popular with former students, wants to be reinstated and is of course, looking for some Benjamins in the form of back pay and punitive damages.

Webb had this to say to the New York Post about being axed:

“I am a dedicated professional and enjoyed being a guidance counselor. I did my job well, and my students and parents thought very highly of me. I would love to return to the DOE and resume the career I have chosen to help and guide students.”

It’s too bad that Webb’s past choices are impacting her in such a way, though it seems her firing was some slick ish done to keep her from getting tenure, so a lawsuit sounds about right. But I think what we can all take from this situation is that what is sometimes supposed to stay in the past, comes back from the dead to haunt you in the future, so you’ve got to be careful when trying to enter fields like being an educator. And we know who to thank for making our past choices are present misery: the good ‘ol Internet…

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