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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. At The Law Offices of Kevin Jensen, we understand how important and stressful the issue of child support can be. You can learn the facts here now all about the family law attorney. 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. A number of issues must be addressed when parents divorce or separate, including child custody. The outcome of this dispute could impact the amount of time you are able to spend with your children, which could negatively affect your relationship with them. Don’t let a child custody dispute impact your relationship with your child–fight for a favorable outcome with the help of a child custody attorney at Pacific Northwest Family Law. You can Check This Out to the best attorney for Trii-cities child custody.

— 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