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Sypher Trial Day 6: Lots of Random People Speak


Today was admittedly not the sexiest of day of the Karen Sypher trial. Yes there were plenty of people who had some type of sexual relationship with Karen Sypher, but at this point it takes a lot to shock me in that regard. Nevertheless, this was the day that the mainstream media decided, “OH!!!! You know what, maybe we should do what that Kentucky Sports Radio goober has been doing and start tweeting out trial details, etc!” One tv station, the Courier Journal and the AP reporter all began to tweet out details at every break, but unfortunately for them, the good stuff was over. Instead of salacious details, today was about the Prosecution wrapping up the loose ends of its case and calling a number of witnesses, each of which was designed for a specific purpose. I had to cut out on the afternoon session, so you will only get a short summary of those folks, but we will pick it up today with the cross-examination of Dana Kolter.


— Kolter was dressed to impress any vixen again today, as he spoke in great detail on cross-examination about his relationship with Sypher and the events that led him to help her. He said that on March 21, 2009, when Sypher came to his home to get him to write the letter to Pitino, “she appeared to be very upset and afraid.” He said Sypher told him that she thought Pitino would try to expose her to the public and she was on her own. This, potentially combined with the oral sex (my words, not his) is what led him to help Sypher.

— Kolter wrote the demand letter to Pitino with Sypher sitting right next to him. He said that she relayed to him the facts and that some of them may have gotten lost in translation (such as the description that it was ‘snowy’, even though it happened in July). He said that Sypher signed a contingency fee agreement that would pay him 10% of any recovery that came about without litigation, and then 50% if actually ended up with a acase being filed. He said he realized how serious the entire affair could be, testifying “I thought it [filing the case] would bring the wrath of God down…I thought it was serious.”

— Kolter was very reflective today on what the entire affair and time with Sypher has done to his life. He was asked what happens when clients call his office and he said “they used to call me”, implying that it had stopped in the past year. Later he said that because of this ordeal, “I have a big “A” on my forehead for the rest of my life.”

— Kolter testified that after he sent the letter to Pitino, he spoke with Pitino’s attorney and financial advisor. Kolter said he wanted to take Pitino’s deposition and even scheduled it, although Pitino did not show up. Kolter was also representing Sypher in the divorce and he said that both cases became interwined in his mind. He also attempted to take the deposition of Tim Sypher, but his lawyer refused.

— There was a great deal of talk today about whether Kolter believed that Sypher could have had a legitimate case. This led to a period where Dana Kolter came off as a community college professor attempting to teach uninterested students on the law. Kolter seems slightly off, but also somewhat intelligent…an odd combination. As he talked about Sypher’s potential Intentional Infliction of Emotional Distress claim, the 5 year statute of limitations, the exception that could toll the period if there was “undue influence” and his belief as to how Tim Sypher could have had such influence, one could have closed their eyes and thought that Kolter was normal. But soon thereafter he would start going off on a tangent about some unrelated fact and he would quickly lose me. I think if one were doing a character study of anyone involved in this thing, Kolter would be the guy….he needs a reality show and someone to explain to me how he didnt get disbarred.

— Kolter testified that despite all of the oddities to Sypher’s story, he legitimately believed her and thought she could be telling the truth. He said he believed “all of my clients”, but also noted that he might have been unduly influenced due to their sexual relationship saying, “I had that problem at times.”

— On re-direct, the US Atty asked why if Tim Sypher had such control over Karen Sypher, was she able to perform sex acts on other individuals. Kolter had no real answer and acknowledged that she had the ability to do things for herself saying, “if she has to seduce a lawyer to get one, then yes she can.”


— When Kolter left the stand, another former lover of Sypher followed, Tyree Fields. Fields was a former businessman, who also was a talent scout in Louisville for the Five Star Basketball Camp. What Fields did with that group wasnt clear as at various times he said he “consulted” with players, was “associated” with high school players and gave advice. Think World Wide Wes but hanging out at the local YMCA.

— Fields said he met Karen Sypher at a mall in Louisville in 2008 and soon thereafter, their relationship became sexual. Fields spoke pretty openly about their time together, saying at various times that they were “very physical”, “very, very sexual” and that they became friends, but only after first being lovers. He also said that Sypher was clear to him from the get go that “she was fertile as a rabbit”, proving that if we know anything about Karen Sypher, it is that she likes to discuss her fertility.

— Fields said he knew that Sypher was married, but she said she was not happy and planning on getting a divorce. They would call and text each other and meet during the course of the next year, and at some point, she told Fields about the alleged rapes by Pitino. She never mentioned to him any threats over the abortion.

— In April of 2009, Fields went to Alaska and when he returned, he read on a website (we will just assume it was KSR or Danny Jett’s Inner Circle) about the extortion threat to Pitino. The mainstream media was not reporting Sypher’s name, but he found it online and then called Karen Sypher. They met in a car and he asked her why this was happening. He then said that Sypher told him “that was stupid…I shouldnt have done that, I know.” Fields suggested this was in reference to the threats, although he said they werent mentioned specifically.

— On cross-examination, the defense attorney dove into Fields’ relationship with people at Louisville. He admitted that he knew Rick Pitino and had been to a few UL practices, despite his “assocation” with high school players. He avoided the question as to whether he may have been “associated” with players that Pitino was interested in, and the topic was not brought up again.

— The defense attorney asked why Fields told the grand jury that he met Sypher in 2007 and now said 2008, and Fields said he didnt know, but this was the correct date. She said that in 2008, Sypher would get angry about the fact that Pitino had a book out that was giving advice, and she didnt understand why a person like him could represent himself in that way after raping her.

— The defense attorney then asked how Fields ended up becoming part of this case and he testified that Steve Masiello, the Assistant basketball coach at Louisville, approached him and then he talked with Masiello and an FBI agent. Fields said Masiello knew about the relationship but wasnt sure how he did. The defense attorney was clearly trying to insinuate that Masiello tried to get Fields to go and have Sypher admit something to him during the conversation where Sypher expressed regrets.


— I was forced to do other things in the afternoon so the detail on these witnesses is not quite as in depth. First was Keith Wise, who was married to Karen Sypher twice, for three years in the 1980s and then six years from 1996-2002. They had four kids together and have had disputes in family court over child support issues.

— Wise testified that he had two different conversations with Karen Sypher on the events in question. The first came when Karen Sypher called him and said she “might have something on Pitino” and that he had offered her $100,000, but she was wanting $500,000. Wise then testified that he told her that he didnt want to know anything about that. The second conversation occurred after Sypher had been charged and she told Wise that the Government had offered her a plea deal. Wise said he begged her to take the plea deal for the sake of the children, but she said “If I’m going down, I am going to take Pitino with me.”

— On cross-examination, Wise acknowledged that he had been held in contempt of court for $23,000 in back child support. He claimed that the boys were living with him at that time and that it was actually a techicality that caused the error, but also later said that ended up paying the money to settle the balance. He said he now does not have to pay child support and his sons all live with him.


— The next three witnesses were all there to testify about Sypher’s decision to charge Pitino with rape via the Louisville police. One was a tv reporter who Sypher asked to come while she filed the report and the other two were officers there that day. What is important about these witnesses is the tape of the interview with Sypher which was played to the jury. Some highlights:

— Sypher comes in to the room and says, “My Mom and I — we wanted to know if we could file charges of rape.” Sypher then describes the night of the alleged incident, saying it took place at Porcinis. She then tells the officer, “I have every right as a citizen to come and file this complaint, I was told before and it’s time to do this…I am going to finally start telling the truth that needs to come out instead of keeping quiet.”

— Sypher asks a number of times if the media will get this and mentions that they are “at the door” while she is doing the interview. Her concern about whether it will go public is a recurring theme throughout.

— A second interview then begins in which the officer makes clear that all statements will be on the record. Sypher tells the officer that she drove to Porcini to meet an executive about a possible job at The Courier-Journal. She said when she was done speaking with the Courier Journal man, she was going to leave but she then saw Rick Pitino at the bar. He invited her to come sit down next to him and have a glass of wine. She said she did because she “didnt want to be rude.”

— She said the conversation began with Pitino and Sypher each talking about their kids, but then it “grew dark.” She noticed the Porcini’s owner and Rick whispering back and forth and she said she knew she was obviously the topic. She said she began to wonder if something was in her drink, as all the customers began leaving. Pitino asked her to stay and order an appetizer with him and soon thereafter they moved to the booth. The Porcinis owner then came by, handed Rick the keys and told him to lock up afterwards.

— She said the food never came, but Pitino showed up with a couple of bottles of wine. She then said he unzipped his pants and began to foce himself upon her. She said she screamed at that point. After he forced himself on her, he asked her to take him home and she said she felt scared and felt like she had no choice but to take him home. So she drove him home and then went home herself afterwards.

— Sypher was reported to be crying in the courtroom while this part of the recording played. She also told the police in the recording that she was forced to have an abortion and said that she was a “devout Catholic” and that Pitino forced the sin upon her. She said Pitino told her that he could not have the baby with her because he “was too well known.

— The Judge then stopped the trial for the day and the jurors were told they would come back to the rest of the tape tomorrow.

So thats where we are. The Government may wrap up its case on Tuesday and then the Defense begins. Nothing too wacky today as the Government got testimony from witnesses that it will use to prove the elements of its Retaliation charge. We will have more tomorrow, as it happens.

Article written by Matt Jones