Is This Fair? NYC Guidance Counselor Fired After Seductive Early Modeling Pics Found Online

October 8, 2012  |  

New York Post

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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  • theplotthickens

    I guess Tiffany is finally getting the notoriety she’s always been looking for. I knew her from back in the day and “those” model pics are circa 2002-2004 and not the 90’s lol. what she did in the 90’s was strip at Scores Gentleman Club til 2005, in between that she would do reality shows here and there she was on fear factor,temptation island,single and the city and Gene Simmons family jewels. She even rendezvoused with Kanye West briefly, she has a couple of groupie tales here and there. However if she is planning to sue the DOE she will lose b/c if there lawyers dig hard enough they will find the dirt they need. 1099 taxes never lie and independant contracters “strippers” usually files those,they will see the timeline while she was teaching she was stripping. Hope she gets the reality show she been so dreaming about.

  • jackieOsassin

    because things like this can and WILL come back and bite you hard on the backside is why you don’t do them in the first place. no sympathy was given, she could have easily modeled just as well with clothes ON and kept her job.

  • I hope she wins her lawsuit, is reinstated, tenured, and compensated. She did not hide a thing from her supervisors, and they screwed her over. Good luck to you ma’am!

    • She might win, but I doubt they will tenure her after this. and would she even accept the position after she was so publically trashed?

  • If I had a body like that ,I would be taking those same type of pics too. IJS

  • Jennifer

    This has everything to do with that $84,000 yearly salary that Ms Webb was going to get. They obviously didn’t care about her past as a model otherwise they wouldn’t have hired her in the first place. People can be so ruthless when it comes to money. Hope she wins the lawsuit, After putting in 12 years as a guidance counselor she deserves her money.

    • NONEYA

      Are you Ms Webb or a relative of hers…you are really going out of your way defending her!

      • ojb

        I’d put this in the ‘just my take’ category (not voting into the ethical or moral merits of Webb, NCY, Jennifer or Noneya)

        I saw nothing unusual in this roll of posts, until i got to your entry. what i mean to say, is that all the comments seem pretty unremarkable. Yes, they are all pretty supportive, but they do all come from different readers – so that ‘Jennifer’ has the three sentences as her only entry. I don’t really have much of an opinion on this story – not enough to post a comment for or against NYC or Webb. What got me to post was N’s comment, because it seems like such an outlier stretch.I can’t imagine how anyone would read J’s comment as an ‘out of’ the way response. I totally get being in support of the city on this (I understand taking that position, at the very least). But interpreting those four lines as a blood relation’s throw down? Just cannot see it.

    • Guest

      How do you know she was making that? I go to school in NYC and all my teachers were complaining about being underpaid. $84K does not seem like underpay to me.

  • Miss Anonymous

    Well, wasnt Vanessa Williams pics put out and she is famous. People should be careful about the things they do in pics especially if they plan on having a good career. Just think If Mrs Obama or her husband had seductive pictures taken when they were younger and it was put out for all to see, would we really take them seriously?

    • L-Boogie

      He admitted to doing coke and marijuana. Um, a picture of underwear is nothing.

      • NONEYA

        But was there a picture of him doing it???

        • Miss Anonymous

          This right here.

  • oh a “student” randomly found the pictures by accident THEN TOLD A PRINCIPAL? yeah right.

    • IAJS

      Right what students are they talking about? The students I know could care less

    • Common sense please?

      Or, the student could have had a grudge. The accessible nature of the pics would make it easy for him or her to act without having to provide any factual basis for a grievance.

      • True, but it just seems too much of a coincidence with her tenure coming up.

  • REllisJones

    Thats why its called the PAST! I am sure there are folks there with stuff they didnt come out about!

    • Miss Anonymous

      Well I hope people keep with the spirit of “the past is the past” and let a ex thief/pedofile/murderer have the benefit of the doubt and let them into their home with their young children.

      There is plenty of people with worst pasts than her but majority of them dont have it on camera/film. The same with the old generation, they did their mess and stuff but they dont have it posted on facebook, and with the stories that I have heard it would make this pic look like a ad in the catalogue for hijabs. People should be VERY careful what they put out on the net because it will come back.

      • Miss Anonymous

        I was being a tad bit sarcastic in the first part. A lot of people like to holler out “oh its in the past, I use to do drugs/prostitute/beat up/maim/etc…” to justify some of their scandalous ways but will in the next minute say ” look at so-and-so drug addicted behind, why we have to help them”. Kind of like older women talking trash about a teen mom whereas they were a teen mom too or “got it handled”.

        • Common Cent$

          Oh ok I follow you.

  • Gimmeabreak78

    I hope she takes them for every red cent. If the school board thought the pictures were inappropriate, they could have saved themselves a lot of time and money and chosen not to hire her in the first place. All they have done at this point by citing her excellent conduct and professionalism through the years is given her ammunition with which to walk away with a hefty settlement. They should spare me their righteous indignation and faux outrage over her so called “unbecoming” behavior because they’ve known about it for almost 15 years now.


    When you take pictures like this just be ready for them to come back and haunt you later in life. Just ask Vanessa Williams!

    • L-Boogie

      It is one thing for a woman to be beautiful but society holds its against her if she uses the very beauty she is praised for. I think it is time for society to get a wake up call.

      • NONEYA

        Being beautiful is one thing but posing in revealing lingerie is totally different, this picture is about sex!

        • L-Boogie

          Um, Noneya. They were modeling pictures. Models do model in underwear. Are you upset at the Victoria’s Secret models?

          • NONEYA

            She looks like she is ready to shot a p o r n movie! Fish nets, and pulling down her panties o-o

      • very true. there are lots of young men and women who pay their way through college modeling. not everyone can afford to send their kids, and scholarships can’t go to everyone.

  • Common Cent$

    I’ll tell you what the city of New York loves being sued. This woman never hid her past letting them know up front that these pictures existed and they hired her anyway smdh. I pray that not only does she get her job back but that she’s compensated for her loss!

    • NONEYA

      If NY has at will employment you can be fired for any reason or no reason at all!

      • Common Cent$

        But I’m thinking she may have some type of union or something because she had hearings right? Or can you still get a hearing with the at will employment?

  • L-Boogie

    Those pictures should not be held against her. Let the woman work.

    • JaneDoe

      Agree.. Let this be a lesson to young ppl. Be careful of the images you put out there. It might come back to haunt you

      • L-Boogie

        Well, I do not have any bad images. But this was done to hurt her.

      • Me

        Yeah, but it also sends a bad message to those who already have pics out: you can’t climb out of the hole that you’re in. Not fair.