As chairman of Donald Trump’s “Florida law enforcement coalition” and one of the Trump campaign’s official pilots, Vincent Caldara is doubly devoted to the Republican presidential nominee and his pledge to crack down on criminality.

A former police officer in New York and Miami, Caldara told supporters at a recent gathering in Florida that he had been flying vice-presidential nominee Mike Pence “from coast to coast to make sure we get the law and order message out to every single person that will be voting on November 8th”.



Caldara is simultaneously fighting claims that he is a lawbreaker himself.

The 55-year-old pilot is charged with aggravated battery with a deadly weapon, after he allegedly drove a vehicle at another person repeatedly in Pompano Beach in July last year. According to court records, the victim, whose name is withheld, was treated in hospital for leg and back injuries. Caldara has pleaded not guilty.

In a separate case, Caldara is accused of severely injuring a woman in June 2014 by recklessly driving into her with his Harley Davidson motorcycle in Fort Lauderdale. The woman is suing Caldara and seeking a jury trial. According to court records, officials have been unable to find Caldara to serve him with a summons.



Caldara and spokespeople for Trump’s campaign did not respond to several requests for comment.

The accusations of wrongdoing against Caldara are only the latest in an eclectic series of claims leveled at law enforcement figures who have publicly endorsed Trump’s campaign for the White House.

Amid a spike in crime in some US cities, Trump on Friday received the endorsement of the national Fraternal Order of Police union, whose president, Chuck Canterbury, said: “Our members believe he will make America safe again”.

But dark spots on the records of some of Trump’s most prominent police backers challenge the credibility of his claim to be the “law and order candidate”. In July, a coalition of dozens of police chiefs and prosecutors pleaded with the Republican nominee to abandon his draconian ideas and embrace contemporary policing theory and criminal justice reform.

Here, the Guardian reviews some of the allegations made against a half-dozen lawmen who have lent their support to Trump’s presidential campaign:



David Clarke

Sheriff David Clarke of Milwaukee County, Wisconsin, has been Trump’s most visible ally among serving police. Although a registered Democrat, Clarke, 60, accused Hillary Clinton’s campaign of “embracing criminality” after mothers of African Americans killed by police appeared onstage at the Democratic National Convention.

Clarke. Photograph: The Washington Post/Getty Images

But Clarke has been accused of violating rules and regulations himself since being elected in 2002. After one of his deputies broke a woman’s neck by crashing his vehicle into her car, Clarke was alleged to have overseen an attempted cover-up that involved framing the woman for drunk driving.

The victim, Tanya Weyker, sued Clarke, several deputies and county authorities in state and federal court in 2014 for compensation and civil rights violations. She said Clarke and his officers continued pursuing charges against her for months even after they knew video evidence showed the officer was at fault.

“Clarke was personally involved in the conspiracy to continue with the baseless prosecution of [Weyker],” the federal lawsuit said, “or, at the very least, was deliberately and recklessly indifferent to his subordinates’ unconstitutional actions and related misconduct.” Clarke and the officers denied the allegations.

An attorney for Weyker, Drew DeVinney, said Weyker settled her state lawsuit for the state-capped maximum $250,000 in compensation, and then settled the federal lawsuit for more than $95,000 for civil rights violations and attorneys’ fees.

Clarke has also come under criticism from within his own ranks. In 2010, deputy Richard Graber, a senior official in the Milwaukee deputies’ union, alleged that Clarke aggressively confronted him, called him a “sick fuck” and threatened to “come after him” for questioning an order that deputies must work mandatory overtime after the high-profile death of a local child.

“Clarke’s profanity-ridden rant included yelling, pointing, and calling Graber ‘waste,’ an ‘organizational terrorist,’ a ‘fucker,’ and a ‘cancer to the agency’,” according to an appeals court filing. Clarke denied most of Graber’s account of their confrontation. A federal appeals court said Clarke’s behavior amounted to an “adverse employment action” but rejected an allegation from Graber that the mistreatment was because of his union activity.

Inspector Edward Bailey, a spokesman for Clarke, declined to comment. “This county office does not involve itself in the current presidential race in any capacity,” he said in an email.

Joe Arpaio

Sheriff Joe Arpaio of Maricopa County, Arizona, has over the past two decades become notorious as “the most unrepentantly lawless lawman in America”: repeatedly condemned by the courts, denounced by civil liberties advocates and forced to pay out tens of millions of taxpayer dollars in compensation.

Arpaio currently faces possible criminal charges for contempt of court for ignoring a judge’s order in 2011 that his aggressive immigration patrols must stop racially profiling suspects. Earlier this year, Arpaio was held in civil contempt on three counts by a federal judge.

Arpaio. Photograph: Ross D Franklin/AP

Less well known than Arpaio’s “Tent City” detention center, however, is his record of using his department to go after personal and political enemies. In 2013, the cofounders of the Phoenix New Times newspaper, which had been investigating questionable real estate deals by Arpaio, were awarded $3.75m in damages after Arpaio’s men arrested them on false charges in late-night raids on their homes.

In 2008, Arpaio had local judges and county legislators indicted on trumped-up criminal corruption charges that later collapsed entirely, resulting in yet more million-dollar payouts to those targeted. The failed charges also prompted the state supreme court to disbar the county attorney, an Arpaio ally, who was found to have brought malicious prosecutions against political foes.

Last year it emerged that Arpaio had even hired a private investigator to look into the wife of the federal judge who ruled in 2013 that Arpaio was engaged in illegal racial profiling. Spokespeople for Arpaio did not respond to a request for comment.

Tim Howard

Sheriff Tim Howard of Erie County, New York, is a co-chairman of Trump’s campaign in the Republican nominee’s home state, which Trump has declared he can win even while trailing Hillary Clinton in state polls by an average of 19 percentage points.

Despite holding an official position in the Republican’s campaign, Howard earlier this year was involved in policing a Trump campaign rally in Buffalo, where he was filmed overseeing the removal of protesters. Aides to the sheriff denied that he had a conflict of interest.

Howard. Photograph: timhoward.com

Howard, 66, has endured rocky patchesin the upstate county – not least on three separate occasions when prisoners escaped or were mistakenly released from his jail. Two of them went on to commit serious crimes before recapture.

In April 2006, Ralph “Bucky” Phillips escaped from Alden prison. He killed a state trooper and wounded two others before being caught after five months on the run. In March 2009, Rasheed Milton was released from the same facility by mistake. Milton was recaptured after raping a woman. Then, in March 2012, Awet Gebreyesus was mistakenly released from Alden after being indicted for the attempted murder of his partner. Gebreyesus was caught before harming anyone.

Howard has also been accused of cronyism after it emerged that companies that gave Howard’s election campaign tens of thousands of dollars in contributions received hundreds of thousands of dollars worth of county contracts for purchases such as new police cars, software and furniture.

Howard’s spokesman did not respond to a request for comment.

Paul Babeu

Sheriff Paul Babeu of Pinal County, Arizona, enthusiastically supports Trump’s anti-immigration stance and campaign pledge to build a wall along the US border with Mexico. Babeu is also running as a Republican for a seat in the US House of Representatives and has made border security a key plank of his campaign.

Babeu promises voters on his website that he will tackle the “hundreds of thousands of illegal immigrants pouring across our southern borders”, warning that at present, “possible terrorists with military training, deliberate plans and lots of money can cross the border”.

In 2012, Jose Orozco, a Mexican man and ex-boyfriend of Babeu who worked for the sheriff’s election campaign, alleged that he was threatened with deportation by an aide to Babeu when he refused to sign an agreement not to publicly disclose the relationship. Orozco’s attorney said she was told Orozco’s US visa had expired, making him undocumented. Babeu denied Orozco’s allegations. An inquiry by the Arizona attorney general concluded that he committed no criminal violation.

Babeu. Photograph: Joshua Lott/Reuters

Babeu has also faced allegations made public by his sister that as headmaster and executive director of a boarding school for troubled teenagers in Massachusetts, he had a sexual relationship with a 17-year-old student. Babeu, who led the controversial DeSisto School in West Stockbridge between 1999 and 2001, responded by publishing his sister’s mental health history.

The former student, Joshua Geyer, has not disputed that he had a relationship with Babeu, but insisted that it was not “inappropriate”. This week, a spokesman for Babeu sent the Guardian a letter purportedly from Geyer that said he and Babeu had no sexual relationship at all. Asked twice whether Babeu himself denied that the relationship took place, the spokesman did not respond.

State authorities pursued DeSisto for operating illegally without a state license. Over the years, the school became notorious for its severe punishment system, and was investigated repeatedly for allegations of abuse and mistreatment of students. It has since closed.

The Babeu spokesman, Barrett Marson, said in an email: “Paul was in charge of the business operations at the school. He never had any control over student discipline or instruction. He was in charge of ensuring there was food and bathroom supplies and things like that. But Paul was never investigated nor had any knowledge of any alleged abuse at the school while he was employed there.”

Wayne Ivey

Sheriff Wayne Ivey of Brevard County, Florida, is playing an energetic part in Trump’s campaign. Earlier this month, he appeared at the opening of a Trump campaign office in Cocoa Beach with Caldara, the campaign pilot.

Ivey. Photograph: Brevard County sheriff's office

“I believe we need a leader that is going to stand shoulder to shoulder with those people that protect our great nation,” Ivey told supporters, “those men and women in uniform that protect our communities.”

Five years ago, Ivey retired as an agent with the Florida department of law enforcement (FDLE) three days after he was accused by a local muckraking website of making a threatening telephone call to a female probation officer who was the ex-fiancee of Ivey’s son, Robert.

A brief review by FDLE of the allegation said that no complaint had been made by the female officer, and that because Ivey was no longer employed by FDLE, the case was out of the department’s hands.

A spokesman for Ivey did not respond to a request for comment.

Scott Jones

Sheriff Scott Jones of Sacramento County, California, pledged earlier this year to support Trump. But Jones, who is also running for Congress as a Republican, has dialed down his enthusiasm after the Republican nominee’s recent string of inflammatory remarks.

“He has not personally or publicly endorsed any candidate, but has said he will cast his ballot for Trump given the only alternative is Hillary Clinton,” Dave Gilliard, a spokesman for Jones, said in an email.

Jones was accused of sexually harassing a junior female deputy starting when he was a sergeant about 12 years ago, which he denies. The deputy, Tosca Olives, said in a sworn deposition that Jones frequently harassed her on visits to the department’s law library, to which she was assigned. Jones denied the allegations.

Jones. Photograph: scottjonesforcongress.com

“It started with, like, rubbing my shoulders while I was on the phone,” said Olives. “It progressed to going underneath my shirt and feeling my breasts. There would be times when there would be kissing. There were times that he would unzip my pants and … but mainly feeling my breasts and kissing.”

She said Jones touched her inappropriately “approximately 30” times. Once, when she told him he must stop touching her breasts, she alleged, Jones replied: “Stop being so tempting.” Olives said she feared retaliation for taking action against Jones, and that when she eventually told him she was going to make a complaint about him, he advised her not to and suggested she would ruin both their careers.

Olives’s testimony was submitted as evidence in a lawsuit brought by four other female deputies, who alleged retaliation and discrimination by the sheriff’s department – much of it in a county jail, when it was run by Jones. Jurors ruled in favor of the female deputies and awarded them $3.6m.

In an emailed statement, Jones said the allegations against him were “without merit, corroboration or evidence” and that he denied them “in the strongest possible terms.”

“I have never been the subject of any internal complaint of misconduct of any kind during my 27-year career with the sheriff’s department, and have consistently opened up my personnel records for review,” said Jones.