Former CPD officer on probation for tax crimes asked judge to end it after just weeks

Diondre Winstead began his career with the Cincinnati Police Department as a recruit in Sept....
Diondre Winstead began his career with the Cincinnati Police Department as a recruit in Sept. 2005. He was promoted to a police officer the following year but quit last year in a plea deal with federal prosecutors.(Cincinnati Police Department)
Published: Feb. 7, 2023 at 11:38 AM EST|Updated: Feb. 7, 2023 at 12:08 PM EST
Email This Link
Share on Pinterest
Share on LinkedIn

CINCINNATI (WXIX) - A former Cincinnati police officer recently sentenced to two years federal probation for tax crimes served just six weeks before asking the judge to end it, court records show.

Diondre Winstead wants to leave Ohio and “essentially start a new life” after struggling to find a job since quitting the police department last year and surrendering his state police training certificate in a plea deal with federal prosecutors, according to a motion filed by his attorney.

The request comes after U.S. District Court Judge Douglas Cole already granted Winstead’s handwritten motion just 10 days after sentencing to fly to Los Angeles on Feb. 4 and then embark on a cruise two days later to Mexico and back. The judge also said he could permanently keep his passport once he returns on Feb. 10.

Less than a month later, his attorney argued in a “Motion to Terminate Probation” that Winstead is not qualified to get a job making the same kind of money he did as a police officer and works as a truck driver “earning substantially less. He has been suffering from a lack of income for almost three years now.”

Federal prosecutors didn’t object to Winstead’s request to go on the 4-day cruise but did balk over his attempt to get out of probation so soon after it was imposed.

“Winstead states that he is making less money and is suffering from a lack of income, which is somewhat belied by his upcoming cruise,” reads the Jan. 4 motion submitted by U.S. Attorney Kenneth Parker.

It’s possible for him to move without ending probation.

“Winstead can request permission for a transfer of his probation but apparently has not attempted to do so. In short, Winstead does not explain how his term of probation is limiting him in a practical or real sense,” the motion states.

“Under these circumstances, asking for the termination of a sentence almost immediately after judgment is unreasonable, particularly when almost no justification is offered.”

Judge Cole denied the request the following day.

Winstead, 45, of Colerain Township, could not be reached for comment for this story Tuesday because, according to federal court records, he is currently sailing on “Carnival Radiance.”

Winstead was with Cincinnati police for a total of 16 years, starting as a recruit in 2005.

FOX19 NOW called his attorney, Brad Moermond, for comment Tuesday and Wednesday. We also emailed him. We will update this story if we hear back.

Read the court records for yourself:

Shortly before his May 31 2022 trial, Winstead pleaded guilty to three misdemeanor counts of filing a false tax return as part of a plea agreement with prosecutors.

Winstead admitted to underreporting nearly $50,000 in cash on his federal income tax returns that he was paid working off-duty details as a police officer in 2015, 2016 and 2017, federal court records show.

He had his tax returns amended to report an additional $49,600 for that time period, according to an affidavit.

Federal authorities originally wanted Judge Cole to put Winstead on house arrest for the first three months of his probation, but the judge didn’t do that.

He ordered Winstead to pay $7,729.07 after the IRS claimed he owed more than $10,000, his sentencing sheet shows.

When he was indicted in September 2021, it was with felonies, not misdemeanors, and he faced up to three years in prison on each charge.

Winstead’s attorney told FOX19 NOW last year all of Winstead’s debts are paid, he corrected his tax issues once the IRS contacted him and he had relied on an accountant other police officers used.

Winstead came to the attention of authorities as part of a money laundering and drug trafficking investigation by several law enforcement agencies into local nightclubs, according to federal court records unsealed in August 2021.

The investigation came in the wake of the March 2017 Cameo Nightclub shooting that killed two people and wounded 15.

Winstead is one of three Cincinnati police officers charged since 2019 with failing to report money they were paid from off-duty details.

Former officer Quiana Campbell and retired captain Michael Savard are the other two.

Campbell was sentenced in 2021 to five years of federal probation after pleading guilty to three felony counts of filing false income tax returns.

Federal prosecutors did not object last year when she requested her probation be dropped early. U.S. District Court Judge Michael Barrett terminated it in July 2022, court filings show.

Savard entered pleas to federal charges of bribery and filing a false income tax return.

Savard admitted to asking for and accepting a $5,000 bribe from an unnamed sergeant to retire early so the sergeant could be promoted, federal court records show.

Cincinnati Police, the IRS and other federal, state and local law enforcement agencies in the Organized Crime Drug Enforcement Task Force were investigating drug trafficking activities “of criminal enterprises and violent street gangs operating in Southern Ohio,” according to an Aug. 18, 2021 affidavit signed by IRS agent Chad A. Adolph.

“Information obtained during these investigations identified alleged money laundering organizations operating as nightclubs supporting and facilitating drug trafficking organizations where drug proceeds were being used to pay popular entertainers to perform at various nightclubs to generate revenue which would appear to be legitimate, reportable income,” the court record states.

During the investigation, investigators received information “that individuals associated with nightclubs had been or were currently being warned of police activities and were in essence, being forewarned of impending investigations and/or enforcement activity and thereby protected by members of the Cincinnati Police Department,” the affidavit continues.

No officers, including Winstead, were ever charged in connection with these accusations.

As part of that case, the sworn statement reads, “it appears members of the Cincinnati Police Department working off-duty details were aware of money laundering activities ongoing in the nightclub and had reason to believe the cash being paid to them was derived from narcotics sales.”

Winstead stated that it was likely he and the other officers were paid with drug cash, according to court records.

He told an IRS agent and a Cincinnati police official he began working details at area nightclubs that had performers and concerts paid for and promoted by “dope boys” so they could clean their drug money through the nightclub, the affidavit states.

Winstead told them promoters of the concerts were “dope boys” who told the owner they wanted to do an event and signed a contract with the club on how much is to be paid to the performers, the club to rent out the space, for security and agreed that the club kept all bar sales and the “dope boys” collected ticket monies, the affidavit states.

He said “dope boys” pay for all the expenses including the cost for officers to be there and the “dope boys” paid for the expenses in cash which came from drug sales, court records show. “Winstead stated it was likely he and the other officers were paid with drug cash.”

Winstead’s attorney has previously and repeatedly said Winstead denies being involved in any money laundering or drug trafficking.

Winstead lost his police powers during the investigation on April 3, 2019, police records show.

At the time, he was a member of CPD’s Honor Guard.

It was the second time he was suspended and lost his police powers since 2016, according to records Cincinnati police released to us in 2017.

FOX19 NOW began looking into Winstead in July 2016. Cincinnati police launched an internal investigation earlier that year into an allegation of “Law Violation by Officer,” police records show.

At the time, Winstead worked in District 4.

He was stripped of his police powers, gun and badge and put on desk duty on June 3, 2016, according to police records.

His police powers were restored nearly two weeks later, on June 15, 2016.

He was moved to another area of the police department. His personnel file at the time did not indicate why.

Winstead was moved to District 2 and remained there until he was put on desk duty in 2019.

It was later revealed through police records we obtained from his 2016 internal investigation that Winstead was suspected by his then-co-workers in District 4 of thwarting undercover drug investigations and tipping off drug dealers about police activity.

The internal investigation closed with the allegation “Not Sustained,” in March 2017, records show.

We requested the entire internal investigation file to review once a police spokesman confirmed in late May 2017 it was over.

Cincinnati police released a few documents related to it at that time.

We were told the full report would not be released for several weeks while privacy redactions were made.

After multiple follow-ups, a police spokesman finally confirmed in late October 2017 the case was once again considered confidential and exempt from the public records law requiring its release due to an ongoing investigation.

In August 2018, former Assistant Police Chief David Bailey was asked about Winstead during a deposition he gave as part of a federal lawsuit filed by a former Cincinnati police officer seeking reinstatement.

According to a copy of the deposition, Bailey responded:

“Officer Winstead was assigned to a (violent) crime squad in District 4. They do some undercover work, narcotics activity. They have the opportunity to work with other agencies. One of those agencies was the Regional Narcotics Unit.

“The commander of the Regional Narcotics Unit (RENU with the Hamilton County Sheriff’s Office) believed that Officer Winstead had advised a suspect of an impending search before arrival, and as a result, they believe that the contraband was discarded. That was the allegation that came to CPD.”

Bailey then stated: “CPD agreed to take on that investigation internally and look into it.”

However, the former commander for RENU, Brad Winall, told FOX19 NOW in a 2017 interview the leader of CPD’s internal investigation section at the time, Lt. Craig Gregoire, called him in June 2016 and asked RENU to turn the case over to CPD to handle.

Winall told us he honored the request, but he and RENU were ultimately disappointed at the outcome of CPD’s investigation based on what they originally were told.

Bailey said in his deposition CPD’s internal “investigation went on for many, many months. As you can imagine, there are things that we would have to do on our end to see if we can mimic that behavior. It didn’t work.

“There was a time where Internal believed that there was the opportunity to - to intervene, they went to District 4. They confiscated some cell phones that belonged to Officer Winstead, and they looked at those cell phones pursuant to a warrant to determine if there was interference with searches being done.

“The outcome of that search I will tell you proved negative. We had no more information. The case was closed non-sustained.”

Then, Bailey said in his deposition, he pulled the accused officer aside and gave him some advice.

“I will tell you, upon conclusion of that investigation, I had Diondre Winstead come to my office and I had a very, very candid conversation with him. I told him what I believed he was doing and I advised him whatever he is doing, he had better stop. He said he understood, he shook my hand and he left.”

“So,” attorney Robert Croskery said, according to the deposition, “when you’re saying that the allegation was not sustained, you’re not saying the conduct didn’t necessarily occur, but rather that you were unable to find evidence to corroborate it that you felt was sufficient, is that right?”

“That’s correct,” Bailey responded.

See a spelling or grammar error in our story? Please include the title when you click here to report it.