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Chris Crowley had neither the fundraising firepower nor the coveted endorsements from local lawmen to match his opponent in the tumultuous race to become Southwest Florida's next state attorney.
But as the former prosecutor took the stage in a dimly lit North Naples restaurant on a sunny Saturday afternoon in late July, Crowley was armed with a conservative political weapon Amira Fox, the chief assistant state attorney for the State Attorney’s Office, did not have in her arsenal.
More:Broken TV set part of what drew Amira Fox to the law; love of prosecution sealed the deal
"He started out as an adviser to Richard Nixon, then he was an adviser to Ronald Reagan, then, of course, he was an adviser to President Trump," Crowley told dozens of supporters who had come to ROW Seafood Restaurant.
"Right now he's advising me. So it's great. I would almost say I have a Republican legend who advised ... the three greatest presidents in American history giving me advice on how to do direct mail properly."
Soon, Stone would tell the crowd that Crowley was the "anti-establishment candidate" who "won't go along to get along" and would "crack down on violent crime."
“That is your choice (between Fox and Crowley)," Stone said. "There is no question that Chris and his campaign are outgunned.”
If the heft of a campaign war chest and the weight of endorsements predicts success, Crowley is facing an uphill battle in his bid to defeat Fox in the Aug. 28 Republican primary.
The winner will succeed outgoing State Attorney Stephen Russell as the top prosecutor for the 20th Judicial Circuit, which covers Charlotte, Collier, Glades, Hendry and Lee counties.
Fox has garnered endorsements from the National Rifle Association and from former and current sheriffs, including Collier Sheriff Kevin Rambosk and Lee County Sheriff Mike Scott.
More:State Attorney candidate Chris Crowley turns himself in, accused of violating campaign laws
She had raised more than $300,000 by late July, drawing on a web of attorneys, law enforcement officials and prosecutors. Fox loaned her campaign $25,000 of her own money. Crowley, by comparison, had raised about $100,000 including $70,000 of his own money.
Indeed, campaign contributions only tell part of the story in the turbulent mad dash for state attorney.
Crowley, 51, grew up in Brookline, Massachusetts, a suburb of Boston, the middle sibling of three.
His father worked as a security guard and died when Crowley was just 14. His mother later remarried and is now a seasonal resident in Southwest Florida. His brother works as a federal administrative law judge for the Department of Veterans Affairs, his sister as a state trooper in Massachusetts.
After graduating from George Washington University in 1990 with a bachelor’s degree in political science and working in Republican politics for a few years, Crowley attended law school at Suffolk University, earning his law degree there in 1998.
In between, in 1995, he joined the National Guard in Massachusetts as an enlisted soldier, later switching over to the Army Reserve. (His current rank is lieutenant colonel.)
“I decided in my late 20s I couldn’t keep jumping around from political job to political job,” he recalled. “It was kind of like being a minor league baseball player.”
More:State attorney candidates spar at debate in North Naples
Crowley’s interest in prosecuting criminals was sparked as a law clerk for the United States Attorney’s Office drug task force in Boston in 1997.
Two years later he was hired by the State Attorney’s Office in Southwest Florida as an assistant state attorney in the misdemeanor division in Naples. He rose to the felony division in Fort Myers soon thereafter.
In early 2004, less than a year after the invasion of Iraq by United States forces, Crowley turned in his suit, tie and legal pad for fatigues and an M16 assault rifle when his unit, the 50th Area Support Group, was called to Kuwait.
Crowley, then a captain in the Army Reserve and in his mid-30s, was part of the Judge Advocate General Corps, which handles a range of legal matters for military personnel.
“I was nervous,” Crowley said of his deployment. “But it was a great experience. I still have some friends I keep in touch with that I was deployed with. It was 11 months in the sand. It was challenging because for a good four to five months it was 130 degrees by 10 in the morning.”
One of those friends is Elroy Schipper, a former member of the National Guard.
Schipper, 46, a plans officer for most of his time at the camp in Kuwait, said he "greatly admired" Crowley for the way he enforced military codes to discipline soldiers.
"As a leader you could count on him," Schipper said.
More:Emails outline concerns about state attorney candidate Chris Crowley's past job performance
After his return from duty, Crowley decided he wanted bigger cases.
He joined the Office of Statewide Prosecution, an arm of the Florida Attorney General’s Office, and worked as an assistant statewide prosecutor there from late 2005 to early 2006. The agency prosecutes crimes that affect two or more judicial circuits, regularly works with state and federal agencies and focuses on complex, often large-scale, organized crime.
But Crowley’s stint as an assistant statewide prosecutor in the Fort Myers branch was relatively brief.
As previously reported by the Daily News, internal emails from Crowley’s supervisor in late January 2006 show Crowley’s boss had concern that law enforcement officials lacked faith in Crowley's abilities as a prosecutor.
Crowley, who is running on promises to establish better relationships with law enforcement and offer improved training for prosecutors, said he wanted to take more cases to trial instead of following what he claimed was a culture of “cutting deals.”
Crowley acknowledged that he would have been fired had he not resigned, but added that he left with a “good reference.”
In late 2006, Crowley returned to the State Attorney’s Office for the 20th Judicial Circuit and worked there as an assistant state attorney in Hendry County before joining the State Attorney’s Office’s post-conviction unit in Fort Myers.
It fell to Crowley to argue in court why a sexually violent predator whose criminal sentence was completed should not be released but instead committed to a treatment facility under the Jimmy Ryce Act, a law named after a 9-year-old boy who was raped and murdered in 1995 in Redland, Florida.
The cases were “the worst of the worst,” Crowley said.
“It was very rewarding,” he said. “Because it was really a question of public safety. I mean, these guys were going to offend again.”
Over his roughly 15-year tenure at the State Attorney’s Office, Crowley earned praise from supervisors, especially early into his career, but later had disagreements over his performance.
Higher-ups commended Crowley for his hard work and called him an “asset to the office” in evaluations from 2003 and 2005, though one noted that Crowley in his zeal would at times “oversell” the strength of a case, “thereby creating unrealistic expectations,” according to his personnel file.
His relationship with his supervisor in the post-conviction unit was not as smooth, records show.
In a lengthy rebuttal to an unfavorable 2008 evaluation, Crowley wrote it “appears my method of effectively prosecuting sexually violent predators is not looked upon well by my supervisor” and defended his abilities as a prosecutor.
Cynthia Ross, the head of the post-conviction unit at the time, replied with a lengthy memo of her own, criticizing Crowley for not knowing the elements of the Jimmy Ryce statute and accusing him of a “lack of attention to detail.”
Another, unnamed assistant state attorney preferred not to act as Crowley’s co-counsel, “because of his poor preparation, his lack of understanding of the law, and his curt and dismissive treatment,” Ross wrote.
His employment with the State Attorney’s Office ended in September 2014, when he was fired for what Russell, the state attorney, later wrote was “poor job performance.” (Crowley said he was not given a reason for his firing.)
But Crowley’s clashes with some of the office’s top figures continued.
In November 2014, Crowley’s attorney sent the State Attorney’s Office a letter, alleging the office had violated federal law when he was reassigned after returning from service in the Army Reserve.
Crowley and the State Attorney’s Office eventually reached a pre-litigation settlement and he was paid $16,000 in back pay.
Crowley now is in private practice in Fort Myers, handling mediation and, mostly court-appointed, criminal defense.
“I like being a prosecutor better,” he said. “But it’s been a great learning experience.”
Crowley’s bid to become the region’s next top prosecutor is no recent ambition. It has been four years in the making, he said.
At campaign events, in interviews, on fliers and at debates, he has portrayed himself as someone who will be tough on crime, especially violent and repeat offenders.
He has repeatedly criticized the State Attorney’s Office for what he claims is a below 40 percent conviction rate he calculated by comparing the number of defendants adjudicated guilty to arrests in a year.
(The State Attorney’s Office has rebuffed Crowley’s claims, saying the methodology he uses is wrong and pointing to a guilty disposition rate calculated by the state that shows a rate more than double Crowley’s and in line with other judicial circuits.)
“I really think there needs to be a change at the State Attorney’s Office,” Crowley said.
Crowley is also quick to rattle off a list of cases he says the current administration botched or didn’t pursue.
There is the 2016 shooting death of 32-year-old Ryan Modell in south Fort Myers. The State Attorney’s Office did not bring charges in that case, citing the state’s infamous Stand Your Ground law.
There are the allegations of animal cruelty cases at several farms in Lee County. The State Attorney’s Office has said the evidence gathered by an animal rights group was collected illegally.
There is the case of 46-year-old Matthew Walker, a Charlotte County inmate who died after an altercation with prison guards in 2014. His death was ruled a homicide, but one juror told the Sun Newspapers jurors were “talked out of” indicting the guards accused of beating Walker. Russell defended his employees.
Earlier this summer Crowley found himself in the crosshairs of investigators.
Crowley turned himself in Aug. 6 after an order for his arrest was issued in connection with allegations that he set up a lottery for his campaign.
The allegations, made in an anonymous tip the State Attorney’s Office passed on to the Florida Department of Law Enforcement, stemmed from a June campaign fundraiser he attended.
Crowley, investigators said, had received $670 from a raffle, which by law cannot be used to raise money for campaigns.
Crowley has said he only found out about the raffle when he arrived at the event and returned the money after contacting state election officials six days later and being told he could not keep it.
He faces felony charges of promoting a lottery and violating Florida's campaign finance law, but agreed to sign a pretrial diversion agreement that allows first-time offenders to have their charges dropped if they successfully complete the program.
Gov. Rick Scott assigned Crowley's case to the 10th Judicial Circuit to avoid any conflict of interest with the 20th Circuit.
During his campaign, Crowley, a lifelong Republican, has sought to tap into Southwest Florida’s conservative base. He has found support among members of the Collier for Trump Club and aligned himself with conservative figures like Stone.
With the help of Stone, Crowley also appeared on a brief segment of a program sponsored by Infowars, the far-right media platform run by controversial radio show host Alex Jones.
(Several major technology companies restricted the reach of Jones and Infowars, which has been criticized for peddling conspiracy theories, in early August and removed some of its content, saying it violated their policies, including prohibitions on hate speech.)
In the video segment posted on his campaign website July 5, Crowley calls into the show and talks to Stone and another Infowars radio host about the alleged animal abuses in Lee County and promotes his campaign website.
To Tom Ravana, co-founder of the Collier for Trump Club, the alleged animal cruelty cases were what solidified his support of Crowley.
Crowley, he said, is a known commodity.
“He’s an honest guy, he’s a straight shooter, he’s a hard worker,” Ravana said. “He knows his job and he is very capable of handling the 20th Circuit.”
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