As many of you know, in 1988, Lynn Tilton distributed holiday cards whose theme can best be described as “Dominatrix Santa” to her ten best clients. Tilton has explained her rationale for doing so in the past (“For many years I had men asking me on the phone each day what I was wearing and what color my underwear was, so I sent out a Christmas card with me in a red lace sort of teddy, and red cowboy boots and a Santa hat, wishing them a Merry Christmas), and when asked again this week by the Wall Street Journal to explain her thinking, added that:

1. At the time, she thought she was retiring and therefore would not have to worry about these pictures coming up again when, say, she was running her own private equity firm and 2. While she doesn’t think she’d “do that today,” she still “own[s] it” when the subject comes up. Something to think about, in case you can’t resist circulating similar photos on your last day of work (Schwarzman).

Billionaire Lynn Tilton’s Biggest Blunder [WSJ via BI]

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Comments (15)

  1. Posted by Brian Fantana | June 25, 2013 at 2:47 PM

    They've done studies, you know. 60% of the time, it works every time.

  2. Posted by Danker_Banker | June 25, 2013 at 3:06 PM

    This year she's putting out a scratch and sniff version.

  3. Posted by Guest | June 25, 2013 at 3:15 PM

    At least she drew the line at sending the clients the VHS tape she made– Sometimes Santa Comes Twice

  4. Posted by HotKarl | June 25, 2013 at 3:35 PM

    Lynn Tilton went to Yale and thus is eligible to become the newest member of IvyConnect. You can find her in the corner at the next IvyConnect mixer getting motor-boated by some Harvard Class of 08 guy who, while having a perfect SAT and GMAT, probably lacks the common sense and real world experience to be able to tell that: A) both the boobs and the tan are fake and B) why it burns when he pees the next morning.

  5. Posted by Guest | June 25, 2013 at 3:41 PM

    No, No, Never.

  6. Posted by Chiarb | June 25, 2013 at 3:52 PM

    WTF does she have to apologize for?

    Middle aged guy who does not apologize for his attraction towards wealthy oversexed middle aged women.

  7. Posted by Guest | June 25, 2013 at 4:02 PM

    I would hit it.

    – Chris Brown

  8. Posted by guest | June 25, 2013 at 4:03 PM

    You're an idiot.

  9. Posted by Anonymous | June 25, 2013 at 4:07 PM

    That Yale Thing

  10. Posted by PermaGuestII | June 25, 2013 at 4:09 PM

    Thank God for thongs.

    -guy who is glad he came of age in the late '90s

  11. Posted by Snarf | June 25, 2013 at 4:14 PM

    Lion o, she looks like she smells …Snarf Snarf

  12. Posted by Clifford | June 25, 2013 at 4:23 PM


  13. Posted by Abe_Froman_ | June 25, 2013 at 4:43 PM

    If those sad sandbags are fake, she deserves a refund!

  14. Posted by The Wild Rover | June 25, 2013 at 4:58 PM

    No, Nay, Never

  15. Posted by gary euelle | June 27, 2013 at 4:30 AM

    Go Lynn!