Collier County sheriff’s reports from 2020 paint a very bleak portrait of Det. Sgt. Kristine Whittaker’s performance as a criminal investigations supervisor.
Three of the four detectives under Whittaker’s command demanded transfers and complained she interfered negatively in their work, berated them, ordered them not to interview certain suspects, ran “secretive shadow investigations” behind their backs, and was “hardly ever in the office,” according to investigative memos obtained by the Florida Trident.
Her direct supervisor, then-Acting Lt. Andrew Dunn, was most concerned however about another issue raised by the detectives – suspected time card fraud, a potential crime.
Ultimately Dunn and three higher-ups – Chief Jim Williams, Capt. Rod Bishop and Lt. John Morrisseau – took the matter to Undersheriff Jim Bloom, who Dunn later testified promised to send it up for a Command Action Review and a proper investigation.
Retribution came quickly, only not for Whittaker. Instead it came for the whistle blowers. In an upheaval of the entire investigations department, Dunn was demoted from his acting lieutenant position back to sergeant and Williams, Bishop and Morrisseau – who together basically ran investigations for the entire agency – were stripped of their duties and re-assigned to dramatically lesser roles, prompting all three to retire from the agency.
And Whittaker? She was promoted to lieutenant, leap-frogging Dunn, the supervisor who attempted to hold her accountable.
Only after her promotion were the claims against her addressed in an “inquiry” by the head of internal affairs who, in an at-times nonsensical report, exonerated her without doing any interviews or substantial investigative legwork.
The case was buried for years before it was revived in an unrelated civil lawsuit that was dismissed last year. One of the deputies who complained about Whittaker, Scott Ventura, testified in that civil case that the Whittaker investigation was “swept under the carpet.”
“No action or legitimate investigation was ever conducted into [Whittaker] as I was informed the ‘sheriff does not want to hear anything negative about his lieutenants,’” he wrote in a sworn statement.
Ventura, who retired from CCSO in 2023 after a 28-year career in law enforcement, further testified Bloom was the leader of a self-protective management crew deemed the “Barbwire Boys,” so named because the undersheriff reputedly has a barbwire tattoo.
“If you’re under the umbrella of the Barbwire Boys you can do no wrong,” said Ventura during a 2024 deposition in the same civil case. “And when they go up [in rank], you go up.”
Echoing Ventura, multiple former Collier deputies say justice was turned on its head in the case because Sheriff Kevin Rambosk and his second-in-command, the hands-on Bloom, operate CCSO as a clique that protects the command staff and the deputies the top brass favors at the expense of fairness, ethics, and the law itself.
Two uniformed deputies on stage
Former Collier Sheriff Don Hunter said the Whittaker case follows a well-worn pattern of whitewashing internal complaints involving favored staff to protect the image of not only individual deputies but of Sheriff Rambosk and the agency itself.
“Here are deputy sheriffs who are told that when you see something, say something,” Hunter said of the Whittaker case. “You have men at the sheriff’s office who did what they were told to do and they were forced out for it, while the person they said something about was promoted.”
As the Trident reported in the initial investigative piece on the sheriff’s office, Hunter himself was the complainant in a case involving Bloom in which the undersheriff was found to have accepted free stock in a company he’d approved for a CCSO armor purchase. Bloom was also cleared after an investigation conducted not by Internal Affairs but by Rambosk’s own hand-picked outside counsel, a process Hunter called a sham.
A request sent to media affairs for interviews and comment from Rambosk and Bloom did not receive a response prior to publication. A detailed email sent to Whittaker, who is now in command of the South Naples patrol division, also went without response.
Ventura said he ultimately blames Rambosk for the lack of accountability at the top of the agency.
“It’s a pattern of favoritism so that nothing reflects badly on the sheriff,” Ventura told the Trident. “It’s a pattern of protecting people and looking the other way and looking for excuses for violations of policies and possible fraud. They cover up for other police officers, which is embarrassing for a police officer to watch.”
Ventura said he was especially embarrassed during an investigative trip to Georgia with Whittaker, and it had nothing to do with the case they were investigating.
It was all about shopping.
“You pay me to watch Netflix movies?”
Ventura said even before he flew to Atlanta with Whittaker to interview a crime suspect, they were both warned by higher-ups about Whittaker’s penchant for shopping.
“She was buying and selling purses,” Ventura told the Trident. “She was told by Dunn, ‘You will not buy purses while you are up there. You’re up there to work.’”
As it happened, their work concluded two days prior to their planned return flight. Ventura said he pleaded with Whittaker to fly home rather than waste two days in a hotel. Whittaker refused to return to Collier County, he said, so she could go purse shopping.
“Georgia is full of outlet malls,” he said. “She’d buy them and then UPS them back.”
Ventura said she took the rental car they were sharing and left him cooped up in his room. Because both were on the clock, it felt like they were stealing taxpayers’ money, he said.
“They paid me to sit in a hotel room for two days watching movies while she went purse shopping,” he said. “We could have left Wednesday and instead we left Friday evening. You pay me to watch Netflix movies?”
It wasn’t the only time Whittaker’s whereabouts while on the clock became a subject of scrutiny. During two consecutive work shifts later that year, her own detectives were unable to determine where she was because nobody saw or heard from during either shift, Dunn wrote in investigative memos.
“This is concerning since Sgt. Whittaker worked an entire overtime shift … and claimed to work an entire day shift yet never entered a Sheriff’s office facility nor was she seen in or around the North Naples Substation by any of the detectives she supervises,” Dunn wrote.
When one of the detectives under Whittaker, Dave McCausland, questioned her about missing a planned “burglary suppression operation” during the day shift, Whittaker told him she was off-site writing an operational plan. But McCausland knew that wasn’t true, according to Dunn, because another sergeant was in the station writing the plan on the same day.
“When confronted with this knowledge [by McCausland] Sgt. Whittaker became upset and walked away,” Dunn wrote.
Most alarming, time card and supervisory issues had also “occurred in her previous assignment [at another CCSO district] and it is clear members that are/were assigned to her have a deep fear of reprisal,” Dunn wrote.
The source of that fear, according to numerous former deputies, was Whittaker’s reputed closeness with Chief Mark Middlebrook, not only a powerful member of Rambosk’s command staff but also the sheriff’s close friend and former brother-in-law.
Ventura said Whittaker told him and others that she was like family with Middlebrook and he was the godfather of her daughter. In a deposition, Middlebrook denied the godfather status but said he’d been friends with Whittaker’s father, with whom he rode motorcycles, for 25 years.
Despite concerns Whittaker might have undue political sway in the agency, Dunn took the matter to his supervisor, Capt. Bishop, who oversaw investigations for the entire sheriff’s office. Bishop went to human resources and pulled Whittaker’s CCSO entry card records and found she had swiped the card one time during the overtime shift at 1:39 a.m.
Just as Bishop began investigating, Whittaker changed both her story and her time card. She deleted the overtime hours to reflect she hadn’t worked that night shift after all. When Dunn was asked to sign a form authorizing the time change, he refused. According to a CCSO investigative memo: “Dunn did not sign the document without an explanation as to why Sgt. Whittaker didn’t work the overtime shift she had signed up to work, didn’t contact the [night shift sergeant], and still put on her time card that she worked the shift.”
Whittaker’s admission that she hadn’t worked the shift made that 1:39 a.m. entry card swipe even more mysterious.
“If she didn’t work, then who swiped her time card early in the morning?” asked Ventura.
There’s no indication in the records trail that question was ever asked or answered.
As potential evidence of time card fraud – which under Florida law can be a crime if proven – and poor supervision grew, Dunn, Bishop and Lt. Morrisseau met with Undersheriff Bloom to request a full internal affairs investigation of Whittaker’s actions. Also involved in bringing the complaint forward was Chief Williams, who was in charge of all investigations at the sheriff’s office.
Ventura said he and Dunn and other detectives were hopeful for accountability. But just days later, on October 15, 2020, the deputies attempting to hold Whittaker to account were blindsided with terrible – and in some cases, career-shattering – news. Sheriff Rambosk sent out an agency-wide email notifying deputies of promotions and new assignments. Dunn explained what happened to him in a deposition in the civil case against CCSO brought by another former deputy, Brian Cohen (the lawsuit alleged religious discrimination and was dismissed last year).
“Once I reported it, we then met with Chief Bloom, and then it was sent up to Command Action Review,” said Dunn. “I went back to work and then when promotions came up … I did not get the position I was in and I was basically demoted back to sergeant.”
He said he believed his demotion was in retaliation for reporting Whittaker.
“Has anyone given you any indication as to why you did not get the lieutenant position?” attorney Maria Mattox asked him in the deposition.
“Basically because of the Kristine Whittaker incident,” answered Dunn.
“Because you had reported Kristine Whittaker?” Mattox asked.
“Yes,” Dunn said.
In the same Rambosk email, Dunn learned that Whittaker, still the subject of those unresolved allegations, was promoted to lieutenant. Ventura said the turn of events shocked many of the detectives and their supervisors alike.
“Every detective knows that Drew Dunn was demoted because he did the right thing, because he did his job,” Ventura testified in the civil case. “You will not find one detective that will say anything bad about Drew Dunn … yet he got screwed and every detective will tell you that. Whereas the other one [Whittaker], ask any detective and they will tell you, if her lips are moving, she is lying. And she got the lieutenant position. So we’re all trying to figure out how that happened.”
Dunn’s demotion was just one domino to fall. Chief Williams, Capt. Bishop and Lt. Morrisseau, though not demoted, were reassigned to new positions in which they were stripped of most of their responsibilities and duties. All three chose to retire, according to multiple sources.
“Clearly their authority had been undercut and diminished severely, virtually to zero,” said Hunter, a friend to all three former high-ranking deputies. “They said, ‘We have nothing to do, but [Rambosk] is going to continue paying us on taxpayer money for doing nothing.’ You took the cream of the crop of investigations and they made them zeroes.”
Hunter said all three ultimately decided they “can’t be affiliated and associated with an agency that lacks integrity.”
In an email to select colleagues before his retirement took effect, Morrisseau said the surprise reassignment – which he didn’t ask for and was never discussed with him – prompted his departure after 31 years at the agency. He also referenced “cancerous behavior” at CCSO, without mentioning names.
“I have great respect for each of you for the way you have always tried to do things the right way and have not given way to the sometimes cancerous behavior at the agency,” wrote Morrisseau, who declined a request to comment for this story. “I will ask that each of you stay focused on what really matters in [the criminal investigations department] … put together prosecutable cases … as you have always done … and look out for each other.”
When contacted by phone, Bishop refused to comment on the case, but in an email he sent to Ventura at the time, the captain seemed apologetic for not getting the justice in regards to Whittaker.
“Not the result we wanted or the collateral,” Bishop wrote. “I echo [Morrisseau’s] words but we have always taken the hard right instead of the easy left.”
Ventura summed up Bishop’s stance in the civil case.
“After everything was said and done, when Rod [Bishop] retired, we talked at that point, and he said, ‘I tried, guys,’” Ventura testified.
Bishop’s wife, Sandra, wrote a letter following his retirement to Rambosk decrying the sheriff for not having the “courage” to speak about the Whittaker fiasco with her husband, which she wrote “destroyed him, damaged a marriage, and devastated our family.” The Bishops were divorced the following year.
“[Bishop] was replaced, embarrassed and removed from his position due to being honest and truthful,” she wrote in the April 5, 2021 missive. “He did not turn a blind eye to what was wrong and/or swept it under the rug like so many. Due to being honest and forthright he was punished.”
She further requested from Rambosk that a “formal investigation” of Whittaker be conducted, but, in a final insult to all of the lawmen whose careers were upended, that never happened.
“How do you close a case without interviewing witnesses?”
Whittaker’s conduct was ultimately subject to a superficial “inquiry” conducted by Capt. Gary Martin, who at the time oversaw CCSO’s Professional Responsibility Bureau. The report is dated June 1, 2021, months after the departmental upheaval.
Martin wrote that for his review he’d read a complaint document, looked at Whittaker’s time cards and HR file, pulled up some federal regulations, and spoke to the agency’s HR director regarding guidelines. There’s no indication he conducted any formal interviews or did any additional investigation.
Despite the scant nature of the effort, Martin exonerated Whittaker fully, writing she had committed no violations. Of the overtime night shift Whittaker later altered to indicate she didn’t actually work, Martin inexplicably concluded she was indeed working that night and found that the mysterious early morning entry card swipe proved it.
“Whittaker used her ID card to make entry into a CCSO facility at 0130 hours, thus confirming she was on duty,” Martin wrote.
Martin failed to note Whittaker had already amended her time card to reflect she actually had not worked the night shift. As for the following day shift during which she also wasn’t seen and had been accused of lying about what she was doing, Martin invented scenarios that might explain how she could have worked despite not being seen and never swiping her card.
“[‘I]t is entirely possible Lt. Whittaker was at another CCSO facility and her card was not used to enter, if she entered with another CCSO member,” said Martin, who has since retired. “It is common to meet others upon entry into a CCSO facility and only one member use their card for the group.”
The rest of Martin’s explanations followed suit, theorizing what might have happened rather than getting answers under oath from Whittaker herself. He wrote that Whittaker hadn’t violated any policies or laws when she stayed in Georgia to shop because she was at the “mercy of the previously booked air travel” and that such travel was regulated under federal labor laws (Ventura said he was specifically told he could change the flight). He said the fact Ventura also was paid for the hours spent idle in Georgia on his time card made it a “non-issue.”
Finally, Martin scolded the chain of command for not meting out discipline on their own rather than kicking it up to Bloom and the command staff – and singled out Dunn, Morrisseau, and Williams.
“If the allegations of the document were factual regarding inefficiencies in her duty performance, these should have been addressed by the acting Lieutenant (Sgt. Dunn),” he wrote.
Ventura, in his civil testimony, said the detectives expected Martin – who he said he thought was a “stand-up guy” – to conduct a good investigation. The former detective ended up shocked Martin “swept it under the carpet,” and never interviewed him or anyone else involved in the case, including Whittaker.
“How do you close a case without interviewing witnesses or detectives who made some serious allegations?” he asked during the deposition. “How do you do that?”
Ventura testified Martin “chose to lie and leave parts out of that investigation to cover Kristin Whittaker, because allegedly she’s buddies with Mark Middlebrook.”
He alleged Chief Middlebrook – Sheriff Rambosk’s close friend and former brother-in-law – took steps of his own to try to protect his family friend Whittaker.
“The power that Mark Middlebrook yields in that place is unbelievable,” Ventura testified. “When the walls started closing in on Kristine, Mark Middlebrook, he tried to [transfer] her … completely bypassing Drew Dunn, who is lieutenant, John Morrisseau, Rod Bishop. … This just baffles me this went on. And yeah I’m frustrated. I’m angry.”
There was some good news in March, though. Dunn finally got the promotion to lieutenant after more than five years of being passed over.
“I’m happy he got it,” said Ventura. “But it should have come sooner.”
The Florida Trident is an investigative news outlet focusing on government accountability and transparency across Florida. The Trident was created and first published in 2022 by the Florida Center for Government Accountability, a non-profit organization that facilitates local investigative reporting across the state. About the Author: Bob Norman is a senior editor for the Florida Trident. His work as an investigative reporter has won dozens of awards and led to criminal charges and the removal of several corrupt public officials. He can be reached at norman@flcga.org.
