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Sypher Trial Day 5: The Men Who Were Seduced By Sypher


Day 5 ended with a bang in the Karen Sypher Trial, as a day of mostly mundane testimony was rocked by a crazy ending with Karen Sypher’s former attorney Dana Kolter. The day was basically a show of men who could not withstand the siren call of Karen Sypher and their testimony showcased her amazing talent. The day began with Tim Sypher finishing his testimony and facing cross-examination, but the star of the show was Dana Kolter, so we will begin with him in our factual recap:


— Kolter walked into the courtroom, looking like a heavier version of John Gotti…if John Gotti lived in Louisville and tried family law cases. Kolter had the appearance of a B-level mafia member wearing a C-level suit, with hair slicked back and a confident walk. He began his testimony by telling the jury that he was a lawyer in Louisville who did mostly civil litigation and family law, but was basically a general practicioner.

— He said that he met Sypher in a parking garage in 2005 as she was in his parking spot (“I pay $90 a month for those spaces, so I stopped.”) He was taken aback by her and she seemed upset…so Kolter tried to comfort her. He gave her his business card and then he left soon after.

— Later in the year, she came by his office to sell holiday cakes for his employees. They struck up a conversation and began talking over the next few months. Then in 2006, on her birthday, they went to a party at a bakery. He remembers because he realized that there was “a connection that men and women have” between them (this was kind of gross to hear him talk about…but nothing compared to what was to come). Both were married, but they ended up kissing during this encounter.

— Then in September of 2006, Kolter hired Sypher to work as a model for his company “Hoosier Daddy” Motor Bikes at a trade show. She worked for him that day and then at the end of the day, gave him oral sex. When it was completed, he asked her if this meant she was his girlfriend, but she did not answer.

— Sypher then got Kolter to write a letter to her husband in 2007, informing him she wanted a divorce. They were still hooking up at this point and Kolter testified that their relationship was more than “strictly business.”

— Then came the part that I may never be able to forget. On Valentines Day in 2008, Sypher came to Kolter’s office in a red jacket and skirt, or as Sypher called it “an outfit appropriate for Valentines Day.” The Government introduced four photographs from that day…three with Sypher posing and then one showing the back of her blond hair, with her head in his lap and a bare abdomen being shown. Kolter testified that Sypher was performing oral sex during this picture. Kolter had taken photographs for his own use of the act being performed.

— On March 21, 2009, Sypher came to Kolter’s house for the purpose of getting him to help her with the Rick Pitino situation. He said she called and came over, and when she arrived, he showed her around the house. Sypher was distraught and told Kolter that Pitino had raped her twice in 2003. Kolter testified he told Sypher to go to the police or the Commonwealths Attorney, but she said she was afraid of what would happen if this went public. He suggested she see a psychiatrist or a different attorney, and attempted to comfort her and make her feel better. While attempting to comfort her, they ended up getting physical (Kolter said that it “devolved or evolved into sex”) and she performed oral sex on him.

— After the oral sex was over, he said he would mull over whether to represent her. Then Kolter became emotion and he said that he went through a “person and professional crisis over this.” Kolter began to cry and said that he was worried that she could be killed and decided he would try and help her. The two parties agreed that he would receive a 10% commission on any money that was won, but it ended up being “10% of nothing.”

— Kolter then agreed to write a letter to Pitino to “try and figure out a way to solve this problem.” While he was at the computer typing, Sypher sat right next to him, watching every word. They worked together to type the letter and in it, they threatened a lawsuit for sexual battery. Kolter says he warned Sypher abou the ramifications and that it would be a big deal and would have a large effect on the community (on this he was correct).

— Kolter was asked whether some of the details of her story concerned him…such as the fact that she drove him home after the alleged rape. He said no, because of the potential for Post-Traumatic Stress Disorder. He also said he didnt find it odd that she said it was “snowy” outside (it was in July) or that she wore panty hose, even though he had never seen her wear panty hose. Kolter said that in the end, “I believed her.” He mentioned that he mentioned the risks, such as that if there was no rape, she had no claim and the Statute of Limitations issues….but still he felt he could go through with it.

— Then things got a little testy. Kolter is sort of a bumbling attorney and he liked to talk about everything and the US Attorney grew frustrated…with his own witness. But of course the Attorney said during his opening that the jury might not like Kolter, and it looks like he was correct. Kolter said that he asked Sypher to write down her claims “under oath” in an affidavit and then recorded her agreeing to the facts of her claim on audio (which was played to the court). He said this is part of why he believed her story. He asked Sypher on the tape if she had sent the man on the phone calls to call Rick Pitino and she said, “absolutely not.”

— Kolter testified that he was told Rick Pitino asked her to make a list of demands, and he believed that he was doing this to try and get her to deny the claims if the caller went public. That was why he believed Pitino asked for the list. He also said he found it interesting the list had a UL mascot on it and that Tim forced her to write it and give it by 4 pm before they left for West Virginia. He saw this as Pitino putting a deadline on the list.

— He said Sypher made him demand for a mediation in 2 days, even though he thought it was a bad idea. Kolter testified, “even if someone raped you, you should be more genteel” in your dealings with the other side. Still he went ahead and made the demand.

— After the FBI was brought in, he saw the agreement signed by Sypher in which she waived attorney-client privilege and thought he had to give file to the FBI. He said that during the course of his 3-week representation, he had oral sex with her three times. He was never paid any money.


— The day actually began with Tim Sypher finishing up his testimony from the day before. He testified that Pitino set up a secret college fund for his daughter that Karen did not know about. His sister was put in charge of the fun, because he thought “that was the right thing to do.” Two $10,000 contributions were put into the fund by Pitino as part of a bonus for Tim Sypher.

— A note was shown in which Tim wrote his wife Karen a card that said, “I said I do 27 months ago today.” It was addressed to “Daisy Mae” and showed that it was from “Hoke.” Tim Sypher testified that these were their pet names and came from the names of the characters in “Driving Miss Daisy.” Tim said that he and Karen used these names as a reference to the trip to Cincinnati for the abortion (I try to refrain from editorial comments…but this is just strange).

— On cross-examination, Tim says that he looked for abortion clinics outside of Louisville at the direction of Rick Pitino, although Pitino never mentioned the word abortion. On the trip to the clinic, he took her to a park and told her that he wanted her to “go to that special place.” The defense was clearly trying to suggest that this trip was a threat to her that she had to get an abortion.

— Tim Sypher then had his least believable strand of testimony, when he said he “couldnt remember” whether he took Karen Sypher to Cincinnati once or twice. He says he may have taken her on August 27, but he doesnt know. The defense attorney showed Tim’s calendar and the fact that he had written down the Aug 29 trip, but not the Aug 27 trip as having taken place. The Defense seems to be suggesting that only one trip took place, contrary to Ohio law and could be implicating that Pitino was able to get them to go around that law….this argument remains to be seen but seemed important to the Defense, as they stayed with it.

— At the clinic, Tim testifies that they mutually agreed to leave his name off the paperwork. The defense shows that the original contact phone number on the paperwork was Tim Sypher’s but then was changed so that one digit was different. When asked why this happened and if it was Tim who did it, he replied, “I might have, I am not sure.” He testified that he paid for the abortion out of the $3,000 given to him by Pitino.

— Tim Sypher then testified, “that day at the abortion clinic…is stuck in my head and she gave me a look I will never forget.” He said, “we hit it off…we clicked.” He was asked if Rick Pitino cared that he decided to start dating the woman that Pitino had sex with previously and Tim said it didnt seem that it bothered him.

— They then went to the incidents after the extortion calls in 2009. Pitino calls Tim Sypher after his “Red Alert” text and says to get to the Yum Center. He gets Karen to come after calling her son Jacob and begging him to bring her. When they get there, they talk suspects but are not able to come up with anyone. Tim mentions that he did not know Lester, who ended up being the caller, saying that “he was like the Easter Bunny…he gave stuff and then would run away.”

— They have a second meeting later that night in the Yum Center and Karen takes off her wedding ring and tells Tim not to come home. Tim said he didnt know what to do but he didnt think about turning it over to law enforcement, that he wanted to find out who was making the calls.

— On March 6, 2009, the events that happened, that could be the major part of the case for the Government. Tim testified that he found out that Karen was at the doctor’s office with her mother and he went there before their trip that evening to West Virginia for the game. He said he doesnt know whether he was invited or not but that he went to check on her and talk about the phone calls. He then asked Karen “what do you want and I told her to write it down.” He testified that he didnt know if Rick had told her in a previous meeting that the things on the demand letter were things he would give her.

— The defense then made a big deal about the fact that Tim Sypher was not invited to come see Karen, thus suggesting she had not intention of writing the letter. The attorney also noted many times that Tim asked Karen to write what she wanted down. The attorney is clearly setting up the argument that Pitino/Tim Sypher were the ones asking Karen to write the note, not the other way around. The attorney asked if Tim had told her to write the “I will protect Rick Pitino’s name forever” language and Tim Sypher said, “you can stop right there sir. I did not tell her to write that”.

— The attorney then asked if Tim called Karen’s son Jacob and told him to make sure and bring the letter before they got on the flight to West Virginia. Tim said he wasnt sure. The defense attorney asked repeatedly why would Tim be in such a hurry to get this demand letter the night before the biggest basketball game of the year for Louisville. Tim Sypher really had no answer.

— He also testified that he did take Karen to the cemetery a couple of days after they got back from West Virginia, hoping that reminiscing at the spot where they got engaged (another odd fact) would make things better. It did for a couple of days, but then things were bad again.

— Tim said on redirect that Pitino did not ask for a list, but that he asked Karen Sypher to write things down so he could remember them. He testified, “things she said and what she wrote down, I dont think she knew what she wanted.”

— On re-cross, two major points were shown by Defense. First, Tim Sypher admitted to buying Karen’s son a car and attempting to buy her a car, both at Pitino-owned dealerships in Lexington. He bought Karen’s son a car at Toyota of Nicholasville and tried to buy Karen one at Lexus of Lexington, with the “Sold” sign even being put on the car. Both happened after the “demand letter” was given.

— The defense attorney then also asked, why would Karen Sypher ask for $75,000 after Pitino left Louisville unless that was a clause that Rick Pitino wanted. He asked Tim why would Karen want her money later instead of now. Tim said he didnt know. He also said he had no idea if Pitino was entertaining NBA offers at that point and defense continued to suggest that the clause was proof that Pitino told her what to put in letter, rather than it being her demand.

The day ended after Kolter and will begin Monday with cross-examination of Dana Kolter, which could be very interesting. Kolter came off as bizarre and the entire affair between he and Karen Sypher a little too gross to think about. His cross should be also full of odd details. As for Tim Sypher, he is done and had some parts of his story torn into a bit. The question as to whose idea was the letter is (along with who made the third phone call) the center of the case so far. Thats it for Week 1…hope you enjoyed it. The rest of the coverage from the week is linked below:

Day 1: The Opening Arguments

Day 2: Lester and the Seconday Characters

Day 3A: The Pitino Testimony

Day 3B: The Guy Who Waited on Pitino at the Bar

Day 4A: Pitino Finishes on the Stand

Day 4B: The Guy Who Married Karen Sypher Speaks

Article written by Matt Jones

56 responses to “Sypher Trial Day 5: The Men Who Were Seduced By Sypher”

  1. PatrickPattersonISwalkingthruthatdoor

    Looks like Rick finally made it to

  2. GeorgeCostanza

    “That’s totally inappropriate. It’s lewd, lascivious, salacious, outrageous!”
    ~~~ Jackie Chiles

  3. GeorgeCostanza

    BTW- Jackie was talking about Valentine’s Day 2008 (this time anyway).

  4. tonygreendoesthestankylegg

    sorry if someone has already coined the term “Karen Siphon” but if they havent, i claim it!!!

  5. E Cat

    Two questions:
    1) Was it ever re-visited or questions about the meeting with the unnamed Pitino “advisor” and Kolter, when they allegedly were negotiating a settlement/payoff?
    2) Has this been more damaging to RP so far than you had imagined?

  6. gmo

    as my dad would say….”that ole gal likes to suck di**!

  7. flemingcountycat

    I have read the entries from matt on this all week, and have really enjoyed it, btw. Pitino realizes she is a psychopath and reveals his info the FBI, his employer, and his family, at which point his publicist dies of a massive coronary, all hell breaks loose in louisville, and he is now revealed a letch, personally and the dog who pissed in the ice cream, professionally. My question is this- How is going public with these details better than just paying her?

  8. Tom

    Please say there is a sketch artist rendition of the Sypher/lawyer photos…

  9. bbobbo

    “The defense attorney then also asked, why would Karen Sypher ask for $75,000 after Pitino left Louisville unless that was a clause that Rick Pitino wanted. He asked Tim why would Karen want her money later instead of now.”

    i’m no lawyer (although i did do mock trial years ago in high school), but shouldn’t this have elicited an, “objection! calls for speculation!” from the prosecutor?

  10. BlueDeuce

    Odd week to say the least! Thanks for the update.

    I guess what I have gathered the most of this trial is Karen Sypher wanted to be inside the circle….the “coaches wife’s circle” and she was hoping laying RP would get her there but it backfired on her. She ended up pregnant (which I don’t think RP did…) and then he cut her loose. So she grabbed on to the closest thing she could…Tim. That went south as he was not as large a fish as she thought he was and then all of this extortion stuff started up when she didn’t get what she was originally after.

    Sounds like a classic piece of trailer park trash trying to get in on the “good life” of the rich and famous! She has failed to say the least and in the end, I don’t see how she gets out of this!

    RP…well, he’ll never let any of this down and I guess, considering what has already been said, what I’m sure will never be known about other ladies…his habits finally caught up to him. Not much else to say really to him other than sleep in the bed you made son! You should of wrote the check and you would still be getting laid by strange women!

  11. Ken T. Ucky

    Before this trial I actually thought Rick got his crony Tim to marry Karen just to keep her out of the way. But reading Matt’s blog entries I now believe Tim really did love her. So I’m glad Pitino is not quite THAT scummy. But what a bizarre relationship Tim and Karen had. Getting engaged in a graveyard and having pet names from the abortion!?!?

  12. tdogg4033011

    11) Everything about the woman sounds bizarre to me as well as slutty …lol

  13. duhville cat

    12) ud still do her.

  14. WalkersGoggles

    just think if this was your mom and they were showing pictures of the top of her head in court!!!! wow!!!

    She’s had half of Louisville in her mouth!

  15. ukcat1

    National media may not be picking up on this but Leno make a joke about it tonight!

    Any one else think that the picture of Kolter looks a little like Bruce Pearl?

    I wonder why there has not been a bunch of other women claiming to have had affairs with Pitino like the Tiger Woods mistress collection. This could not have been an isolated quickie?

  16. Calipari'sInYourEar

    #7 – flemingcountycat – Because this woman lost her mind.

    You pay her any amount, and she burns through it and comes back for more.

  17. Calipari'sInYourEar

    I wish the prosecutor would take an open tally of the courtroom via a show of hands by asking, “Who in this room has been blown by this woman?”

    That’s when Billy Gillispie stands up in the back row and claims he’s the one that made the 3rd phone call.

  18. Calipari'sInYourEar

    #14 – WalkersGoggles – If Karen Syphers son doesn’t know she’s a whore by now then he’s missing the short bus to school on purpose.

  19. Calipari'sInYourEar

    Has Karen Sypher given more blow jobs than the Kentucky Basketball team has won games?

    I say by a country mile.

  20. Straightbent

    Jones, I am loving these updates but we need to have a live blog so we can ask questions. Happy Saturday!

  21. JP

    What’s the equivalent of a Pulitzer for bloggers?

    This train wreck has been utterly fascinating all week long. What a cavalcade of odd characters. I can’t look away even if I feel dirty afterwards. lol If she does take the stand…wow.

    Thanks for all this stuff this week Matt! Apparently real court is nothing like Matlock. I’m looking forward to next week for sure.

  22. Calipari'sInYourEar

    When this bimbo is carted off to jail within the next week… what will she be screaming as they are dragging her out of the courtroom??? Will she drop some more bombs?

    Can we get a thread for suggestions?

  23. GoCats2010

    so John Wall retweeted a tweet that dropped the “C” bomb…there are very few words that should never be used, but that is one. He’s gotta be feelin’ ripe if he’s RTing that at 1:30am, he’d been doing a good job too

  24. tdogg4033011

    13) nahhh, not this ole boy. I’m a married man, that actually means something
    to me. She is a slut, no if ands or buts about it

  25. DaveUK

    Matt – thanks for the details this week! You’ve been doing a great job! I haven’t seen much from the defense yet on the “accessory/complicit in extortion” angle aside from the “Pitino asked for a list” portion. If these men were exercising influence on Karen S.’s actions regarding writing her “needs” in the letter, they have to be included in the charges or have been provided immunity in exchange for their testimony. Both are in dominant and assertive roles (husband, attorney) and it could be established quite easily that she relied on them to advise and protect her and do what is right, and there was never any intent to extort. Ultimately, I think she’ll be acquitted but the images in our heads will live forever.

  26. NotTheSlickistRick

    19) Maybe she should get some shirts for her fan club BJ2K

  27. duhville cat

    24) …. And that’s a bad thing?

  28. CalifCatFan

    Why haven’t we heard from BPsycho? This comment section is not complete without the wit and wisdom of BPsycho.

  29. billwill431

    damn i swear i didnt read the “sticky ricky” urban diction post 1 posted till after I made my comment. But they got it wron a Sticky Ricky is when you go for a Dirty Sanchez but end up pre ejaculating on your self.

  30. BigBlueSwagger

    It’s a good thing I’m not on the jury because this woman would be going down! pun intended 🙂 She clearly abuses her assets for personal gain (not that I actually find anything wrong with it; I’m female & have used “the girls” to get drinks bought for me). But Sypher takes it to a whole new level~ she uses sexual favors to get jobs and exchanges her talents for help. Truthfully, I don’t think I realized exactly how much men think with their other head…. So far, she’s had relations with a gas service man, a newspaper exec, an attorney, a coach, a coach’s pawn that she was at least married to and we’re only a week into the trial. And of those men, at least 3 of them were married. She is nothing but a gold-digger, home wrecking, name dropping ho.

    And if you haven’t followed the articles related to her, here’s another dandy that sounds uncannily familiar….

  31. BigBlueSwagger

    Oh and while I’m at it~ Pitino deserves what he’s getting. I’m sure he’s had his own share of trysts and while I’m a fan of his from a coaching standpoint (I just can’t forget that he brought UK back to it’s glory), I’m not a fan of his from a personal standpoint. He’s dirty. But for all intents & purposes of this trial, Sypher is obviously a crackhead. Rape? And then driving him home? And then meeting him in a private residence? Seriously??? Even if she isn’t found guilty, she sounds like nothing but a big ol’ slut who would give head to just about any Hairy, Dick and Tom… LOL

  32. bluebiscuit

    The more that is revealed by this trial, the more of a mystery it seems to be. A nasty mystery.

  33. NotTheSlickistRick

    With all the time she has spent going down she must have the knees of a 50 year old NFL lineman.

  34. JohnB

    You’re right Kolter looks like Gotti. Is that a pinky ring Kolter is wearing? That would say it all.
    The only conclusion from this trial is Karen Sypher is trash, Pitino is trash, and his friends are trash. Welcome to Pitino World.
    Pitino’s family and other families deserve our sympathy, not them.

  35. SexnNursinHomes

    I’d tag sypher

  36. NotTheSlickistRick

    35) Sex I used to think the only requirement you had was that she had a pulse, now I’m not so sure that is optional. LOL

  37. Boggie

    Never underestimate the power of good BJ.

  38. SexnNursinHomes

    36- haha, don’t kid yourself! Only thing left on my bucket list is necrophilia.

  39. NotTheSlickistRick

    YIKES you are truly DA MAN

  40. NotTheSlickistRick

    BTW I have a friend of a friend that hit that several times(even before this all came out, while Tim was at away game). He says she damned near killed him. What a disappointment Quicky Sticky Ricky must have been.

  41. SexnNursinHomes

    40- hahaha, that’s hilarious! May be your buddy could give QSR a few tips.

  42. bigbluedude

    john gotti would have never banged skanks as nasty as karen. he had top of the line ho’s

  43. NotTheSlickistRick

    Tips for Quicky Sticky Ricky
    #1 Wait until after dark
    #2 Never be seen with her in public
    #3 Take your time
    #4 Allow 2 days to recover
    #5 Leave all self-respect at the door
    #6 Hide your rabbits
    #7 Make damn sure she is satisfied
    #8 Block out everything she says

  44. SexnNursinHomes

    43- your killin me this morning!! hahaha

  45. GeorgeCostanza

    OT- Tyreke Evans video released from wild ride on I-80 (up to 130 mph)

    Someone must have given him the finger.

  46. NotTheSlickistRick

    44) feel free to add to the list, it should make for an entertaining day 🙂

  47. GeorgeCostanza

    Bigger Story…
    WikiLeaks or
    RikiLeaks ?

  48. GeorgeCostanza

    Serious note: WikiLeaks sucks!

  49. catty

    Thanks once again for this terrrrific write up! I agree with a previous poster that we need a live blog on this. Or a “Send Matt your questions” and you’ll post the answers.

    I am interested in the audience and jurors reactions to the BJ pictures.
    Do you think the fact that she an adulteress and major mouth hugger will sway the jury to convict on that. poster #30 seems to imply she would convict on that.

  50. catty

    #15–My thoughts has to why no other women have come forward like they did with Tiger? Tiger’s women all are getting something they want by coming forward MONEY and FAME. The women Rick may have slept with…The National Enquirer doesn’t care enough about this to pay them $$$. Plus Kentucky society is a lot different from New York and Vegas. These women wouldn’t be able to live with the notoriety and some probably were married. Of course that’s only if Rick went outside the lines any other times.

  51. Waitin' on 8

    Did Tim Sypher mean to say that Pitino has been looking for an NBA job “at some point” in the last 2 years? Sypher’s statement about “at that time” seems to point toward Pitino looking for the NBA. Oh no! What will UofLOL fans think?

  52. Waitin' on 8

    Would it be more fun if Pitino left or stayed?

  53. BigBlueSwagger

    Catty~ I indeed would convict her. Sypher’s reputation and (lack of) character lead me to believe that she is capable of committing extortion. I’m no saint but her multiple sexcapades with married men (and many while married herself) distinctly leave a very bad impression. I’m fairly certain there’s not a man on this blog who she wouldn’t spread her legs or open her throat for~ assuming she could use his services for her own benefit (to be her lawyer, make threatening phone calls, be her handyman, offer her a job, etc…)

    IMHO, her motivation is simply money. This isn’t her first attempt to ‘seduce & get rich from it’ scheme either.
    Final piece of evidence that shows her true character comes from KSR itself…

    While I know that jurors aren’t supposed to consider any evidence outside of the court proceedings, I personally find it difficult to believe that she is a victim… She is a dirty ho.

  54. catty

    53- I agree she is a nasty nasty woman, but that doesn’t make her an extortionist. Just like it doesn’t make her a murderer.

  55. BigBlueSwagger

    Hey Catty~ I understand what you’re getting at, as someone Saturday’s post with the demands list questioned me on that too. This is my reply…

    I fully believe she attempted to extort Pitino, without specifically saying “This is a blackmail”(her demands imply extortion IMO). As indicated by the 2 links (in #53), she’s already tried to hang one man out to dry and basically laughed off her childrens’ attempts to find her a sugar daddy (and truth be told, I wouldn’t put it past her to have placed the profile herself. And another thing~ what does it say about the way her children view their mother IF they actually did post her profile on
    I understand your comment about my post & perhaps I should have stated it differently. My point is that considering Sypher’s history of using her sexual talents to exploit men and gain an advantage, I believe that she did attempt to extort Pitino. Crying rape just made her appear even guiltier in my eyes. If a man had raped me (I’m female), you can be damn sure I wouldn’t be around him at the same parties, locations, private residences, driving him home immediately afterwards. So yes, I would base much of my decision to convict her based on past behavior because I think it demonstrates patterns, tendencies, and is a good predictor of the likelihood she would do said activity again.

  56. Letcher County

    Great coverage!! Keep it up.
    P.s. Sypher is a hose beast.