The Arpaio All-Stars: Meet the county sheriff’s sketchy retreads

Despite giving Joe Arpaio a birthday hug in June, new Maricopa County Sheriff Jerry Sheridan has repeatedly and publicly distanced himself from Arizona’s most infamous law enforcement officer.

Sheridan may have been Arpaio’s second-in-command back in the day, but he insists he has no interest in using his office for immigration enforcement. He promises to fully comply with the orders of federal Judge G. Murray Snow, who has kept the sheriff’s office under his thumb for more than a decade as a result of the Melendres v. Arpaio racial profiling lawsuit (now Melendres v. Sheridan). The message from Sheridan is clear: He ain't no Sheriff Joe.

It’s true that the 58-year-old Sheridan is a pale shadow of his Machiavellian former boss, who once bestrode Arizona like a gloating, malevolent colossus. But it’s not quite true that Sheridan’s reign carries no Arpaio-esque echoes. Like his erstwhile jefe, Sheridan inexplicably rocks five stars on his collar. (The standard is usually four.) And Sheridan occasionally espouses revanchist fantasies of bringing back a revamped Tent City or beefing up the much-diminished sheriff’s posse — both old calling cards for ol’ Joe.

Other signature Arpaio policies — like pink underwear, chain gangs and green bologna — have yet to make a comeback. But Arpaio-era people, especially those with pockmarked records, certainly have. To fill out his command staff, Sheridan has drawn heavily from ex-Arpaio minions.

Since taking office in January, Sheridan has hired, re-hired or promoted at least four notable figures from the notorious Arpaio era, surrounding himself with some of the same badge-wearin' bubbas who helped place the sheriff’s office under federal scrutiny in the first place. One retired sheriff’s office insider, who asked not to be named, called the new command staff “Arpaio light.”

“You can't say that you're not like your former boss when you're checking all the same exact boxes that your boss checked,” the insider said. “It's the same players, the same roster.”

Among those Arpaio all-stars are:

• Paul Chagolla, who once reportedly threatened to call Child Protective Services on an uncooperative local reporter
• Jeff Gentry, who led a unit that was often sicced on Arpaio’s biggest critics
• Steve Bailey, who was once recommended for federal contempt proceedings
• Chad Willems, a political strategist with zero law enforcement experience

Sheridan’s even brought back old-timer Rollie Seebert to be his executive chief of custody. Seebert, who retired in 2012, had been gone so long that county officials had a hard time finding his personnel records when Phoenix New Times asked.

Sheridan may be “putting the band back together,” the insider said — only “they’re a lot older and don’t sing as well.” But it’d be a shame to forget their greatest hits.

Here’s a refresher on what Sheridan’s moldy-ass crew of flunkies did so poorly the first time around.

Paul Chagolla, Deputy Chief

Chagolla is a one-time acolyte of Arpaio’s former second-in-command David Hendershott, whom Arpaio fired in 2011 in the wake of an abuse of power scandal that threatened Arpaio’s reign.

For many years, the rotund Hendershott literally and figuratively played the heavy for Arpaio, retaliating against anyone inside or outside of the sheriff’s office not sufficiently deferential to Sheriff Joe. That included recalcitrant employees, judges, county supervisors and mayors. It also included the former owners of New Times, who were arrested in 2007 after the paper exposed bogus grand jury subpoenas seeking identifying information on New Times’ online readers.

Chagolla was once a much-despised member of Arpaio’s public information unit, with a well-earned reputation for puerile, bellicose behavior toward journalists. In 2011, an outside investigation revealed that Hendershott and Chagolla had threatened a local reporter with arrest for refusing to cooperate on a probe of county officials. They warned her “several times” that if she did not comply, Child Protective Services would take her kid.

Arpaio’s top in-house flak told investigators that Chagolla was “clearly under the thumb and influence of...Hendershott.” By that time, Chagolla was no longer doing PR for the sheriff, having been promoted from lieutenant to deputy chief.

After Hendershott was fired, Chagolla remained with the agency. When Paul Penzone became sheriff, he busted Chagolla down to captain in command of a district that included that hotbed of crime known as Sun City. Pressed on Chagolla’s continued employment in 2018, Penzone said Chagolla had his support and had worked hard in the community, offering, tongue in cheek, that Chagolla was “deserving of the position he currently holds.”

A few weeks after being sworn in this January, Sheridan promoted Chagolla to resume the rank of deputy chief as commander of the sheriff’s Patrol Resources Bureau. Chagolla now oversees several divisions, including aviation services, SWAT and court security. According to a county spokesperson, his annual salary is $207,408.

Jeff Gentry, Undersheriff

A stalwart Sheridan apostle, Gentry scored the plum position as Sheridan’s “undersheriff,” which is the same role as chief deputy, but perhaps without the negative connotations that resulted from Hendershott’s misdeeds in that role and later those of Sheridan himself.

Gentry, who retired from the sheriff’s office in 2020, was once the sergeant of the Selective Enforcement Unit — formerly known as the Threat Assessment Squad or Threat Management Unit — which was involved in many questionable capers in the Arpaio days. The unit was accused of targeting political opponents and critics of Arpaio, often at the behest of Hendershott.

Hendershott would later take credit for the unit’s 2007 nighttime raids on the homes of former New Times’ owners Michael Lacey and Jim Larkin, ending in wrongful arrests that spawned a lawsuit that the county paid $3.75 million to settle. Hendershott also reportedly sicced the unit on Nick Tarr, a Sheriff Joe impersonator who went by the name of Joe Arizona and wore a trick-or-treat style getup involving an old Department of Public Safety shirt and a pair of pink boxers. Hendershott ordered members of the squad to cite the comedian for “impersonating” a law enforcement officer.

Additionally, Hendershott used the squad in 2004 to help smear Arpaio’s political rival at the time, former Buckeye Police Chief Dan Saban. The sheriff’s office boosted the unfounded allegation that Saban had raped his adoptive mother when he was a teen, supposedly more than 30 years prior to her decision to report it to the sheriff’s office. Saban insisted that he was the victim in the episode, but the smear did undeniable damage to his candidacy. It was the kind of character assassination the KGB perfected during the old Soviet Union — known as kompromat, at which Hendershott was a past master.

During the Saban investigation, Gentry, then a detective, interviewed Saban’s adoptive mother and wrote up the report as ordered. His superior at the time was along for the ride: Sergeant Steve Bailey.

According to a Maricopa County spokesperson, Gentry’s salary as undersheriff is $209,636.

Steve Bailey, Executive Chief of Enforcement

Bailey, a former sergeant of the threats squad who was directly involved in both the Tarr and Saban investigations, is Sheridan’s pick for executive chief of enforcement, which oversees all enforcement and detention personnel. Sheriff’s office spokesperson Chris Hegstrom confirmed that Bailey has been offered the position, and Bailey told New Times that he was inclined to take it.

“I’m pretty sure I’m going to do it,” he said. “I’d like to be there sometime this month.”

Bailey said he would report to Gentry in the new role, a man he had known “for years and years.” He added that he believed Sheridan was “doing it for the right reasons” and that “this might be a really good chapter for the sheriff’s office, without all the sideshow nonsense, if that makes sense.”

But back in 2015, both Bailey and Sheridan were knee-deep in that very sideshow — particularly the civil contempt trial of Arpaio and his underlings before Judge Snow.

Snow had discovered that Arpaio and the sheriff’s office were violating his orders not to enforce federal immigration law. Snow also discovered that Arpaio was using a confidential informant in Seattle, a supposed computer wiz with a dubious past, to investigate a cockamamie conspiracy theory that involved the Obama White House, the Department of Justice, Snow and a law firm working for the plaintiffs, among others. The judge ordered the sheriff’s office to cough up all records having to do with the “Seattle operation,” plus evidence related to the agency’s violation of his orders.

Instead, the sheriff’s office attempted to hide the existence of 50 hard drives related to the Seattle investigation and nearly 1,500 IDs that had been confiscated by the agency, many of them from Latino drivers. Snow was pissed when he found out about the cover-up, ordering the U.S. Marshals Service to seize the evidence. Both issues became part of the contempt proceedings.

By this time, Bailey was head of the agency’s Professional Standards Bureau. As captain of PSB, he’d opened an investigation into the 1,500 IDs, which he later told the court Sheridan ordered him to pause. Ultimately, Snow concluded that Bailey gave a “knowing and false report” to the court’s monitor about the existence of the IDs and referred the matter to another judge for possible criminal contempt proceedings. Bailey was spared when the Department of Justice eventually took the position that the one-year statute of limitations on contempt of court had expired.

Arpaio was later tried and found guilty of criminal contempt, only to be pardoned in 2017 by President Donald Trump.
Unlike Sheridan, whose prevarications and misconduct earned him two civil contempt citations from Snow and a spot on Maricopa County’s “Brady list” of cops with honesty issues, Bailey eluded any lasting consequences. He retired from the sheriff’s office in 2017 and until recently had been working at his own security firm, RPI Consulting, in Chandler.

Bailey insisted to New Times that he “pushed back hard” on some of the things Arpaio wanted and had “testified truthfully” before Snow — which, he said, displeased Arpaio. Asked if he thought his work for Arpaio cast a pall over his career, he said that he hoped not. “Sheriff Arpaio just did things differently,” he said. “I didn’t always agree with it.”

Bailey said he thought he made “good decisions” in the Arpaio years. Sheridan, Bailey claimed, never asked Bailey or others to do anything hinkey because it was “never part of his DNA.”’

Bailey’s salary for his new role has not been made available to New Times.

Chad Willems, Chief of Administration

Willems was Sheridan’s political consultant and fundraiser, a service he also performed for Arpaio for many years. After helping Sheridan to an election win last fall, Willems now gets to call himself the “Chief of Administration” for the sheriff’s office.

According to Willems’ LinkedIn page, he has zero experience in law enforcement, but he has loads of experience in raising money for politicians. Over the years, Willems raised millions for Arpaio, and for himself in the process. Willems' clients of yore include notoriously racist state Sen. Russell Pearce and the medical marijuana industry.
During the 2024 election cycle, Willems consulted for Sheridan’s campaign, earning $364,000. Now, Willems is being paid $185,000 for what a sheriff’s office spokesperson described as a “chief of staff” position.

As they say, to the victors go the spoils, all of it at taxpayer expense.

‘Slendershott’

Perhaps the biggest Arpaio retread is Sheridan himself. The newly minted sheriff’s early track record in office is both self-serving and less than inspiring.

During the 2024 campaign, Sheridan tried to downplay the actions that landed him in hot water with Snow, to the point of severely distorting the historical record. Then there was his failed attempt to cancel his first court-appointed monitor meeting as sheriff, and his announcement that the sheriff’s office would no longer screen employees entering county jails for drugs and other contraband, despite a rash of drug overdoses in the facilities.

And there are his repeated mischaracterizations of the state of the sheriff’s office’s compliance with Snow’s orders. For instance, in a recent interview with Jim Sharpe on KTAR’s AZ Political Podcast, Sheridan asserted that his agency was down to a four-second discrepancy between stops for white versus Hispanic drivers, which Sheridan called “pretty darn good.”

Not quite. The sheriff’s office’s own Traffic Stop Annual report for 2024 showed a 14-second discrepancy, which differs from Sheridan’s figure by a full New Year’s Eve countdown. A sheriff’s office flak admitted to New Times that Sheridan misspoke. In a 2014 training session with deputies, Sheridan notably scoffed at the idea that even a 14-second discrepancy is significant. In that same training session, Sheridan called Snow’s order to cut out the racial profiling “ludicrous” and “crap.”

As local politicians and commentators bitch about the more than $300 million price tag for Snow’s mandated reforms, it’s worth noting that Sheridan is a big reason the case has lasted so long and cost so much. Snow has reinforced and broadened oversight of the sheriff’s office’s internal affairs investigations, finding that Sheridan and Arpaio “willfully and systematically manipulated, misapplied, and subverted” internal investigations “to avoid imposing appropriate discipline.”

Sheridan also signed off on ridiculous investigations like the Seattle operation (at a cost of $250,000), described Arpaio in print as a successful and dedicated public servant and fostered a laissez-faire office atmosphere that benefited a favorite detective who admitted to sleeping with the female victims of crimes that the agency was investigating.

Phoenix civil rights attorney Joel Robbins, a well-known Arpaio foe who has sued the sheriff’s office numerous times, says he’s not impressed with Sheridan, whom he used to refer to as “Slendershott” because Sheridan “wasn’t fat like Hendershott.”

When Penzone was elected over Sheridan in 2016, Robbins said, “our business fell through the fucking floor.” But he was OK with that.

“It was the best day in my fucking life, because I solved the problem,” Robbins said. “I didn't just get money for a problem.”

But now, with “Slendershott” back in the saddle and a “City Slickers”-style cowboy hat on Slendershott's native New Yawker noggin’, Robbins said he’s back to suing the sheriff’s office again. It’s business he doesn’t want.

“I don't want people to get hurt,” Robbins said. “I would rather have a good sheriff that actually gives a shit. But he's bringing back the bad guys, ya know?”

This story is part of the Arizona Watchdog Project, a yearlong reporting effort led by New Times and supported by the Trace Foundation, in partnership with Deep South Today.