Don Morrissey’s career has been in free-fall since June, when he made parts of his personnel file public by suing to appeal his second demotion.

The veteran lawman resigned as president of the Santa Clara County Deputy Sheriffs’ Association (DSA) in July after San Jose Inside exposed the extent of his role in a texting scandal involving reams of bigoted messages. Just last weekend, he gave up his badge after 19 years at the Sheriff’s Office, and public defenders are now analyzing 16 of his 87 arrest cases for potential bias. (The remainder weren’t handled by the Public Defender’s Office, but could still be subject to appeal by the defendants).

Recently obtained information sheds new light on how extensively sheriff’s candidate John Hirokawa has been involved in running interference for the one-time union chief.

San Jose Inside has now learned that Morrissey, who already plummeted from lieutenant to transit cop, was the subject of yet another investigation into alleged wrongdoing when he resigned from the agency last week. Sources at the Sheriff’s Office say he tried to meddle in a probe involving a deputy with suspected ties to the Hell’s Angels motorcycle gang—the same investigation that unearthed the text messages that led to Morrissey losing his sergeant’s stripes in 2016.

Morrissey went from being a “rising star,” to cite a retaliation claim he filed against Sheriff Laurie Smith, to a liability for the county, his union, his profession—and his preferred candidate for sheriff.

During his time as head of the DSA, Morrissey positioned himself as one of Sheriff Smith’s most strident critics. He supported her opponents in the past two elections—retired Capt. Kevin Jensen in 2014 and retired Undersheriff John Hirokawa this year—because he said he wanted to reform the troubled agency, which has grappled for years with the high-profile murder of a mentally ill inmate, a series of excessive-force lawsuits, a higher-than-national-average jail suicide rate and soaring overtime spending.

But Morrissey’s history of misconduct eventually caught up to him, compromising his role as watchdog. Politically, it also made him a thorn in the side for Hirokawa, Smith’s former second-in-command and jails chief who has tried to portray himself as a reformer despite decades as part of the same administration he’s opposing and his years-long affiliation with a wayward, and arguably corrupt, cop.

As a candidate, Hirokawa has criticized Smith for failing to hold officers accountable, playing favorites and meting out discipline based on personal retribution.

“Setting a higher standard for all officers starts from the top and permeates down through the department,” Hirokawa wrote in a July 5 press release issued after San Jose Inside’s reporting prompted him to publicly denounce Morrissey. “The current leadership of the Santa Clara County Sheriff’s Office has failed to set this standard over four decades, and that is the core root of the problem. The current leadership ... were the ones that ultimately decided what the disciplinary action would be for this texting scandal and they are the ones that should answer to their decisions.”

While Hirokawa may have been unaware of the latest probe into whether Morrissey’s interfered with a criminal case, the candidate has known for years about the ex-deputy’s alleged ethical lapses. San Jose Inside has obtained non-public depositions from last year that shed new light on Hirokawa’s participation in efforts to give disgraced former union president good assignments within the department after he’d been disciplined for porn surfing and trolling for Craigslist sex on the clock.

A 242-page transcript of a Sept. 18, 2017 deposition shows that Hirokawa also advocated on Morrissey’s behalf in an internal affairs investigation after his participation in a texting ring involving misogynistic, racist and transphobic comments prompted a follow-up disciplinary action. Hirokawa additionally served as a supportive witness in Morrissey’s union-funded wrongful demotion lawsuit against the county.

The Morrissey-led DSA later provided Hirokawa with its endorsement and $246,588—nearly double the amount the candidate raised himself—in independent expenditures, which forced Sheriff Smith into her first runoff since being elected to the office in 1998.

However, newly unearthed records affirm that Hirokawa’s defense of Morrissey predates his run for office. In 2012, when the officer was found using his work computer for porn and sex ads and was accused of lying after he falsely claimed it was part of a prostitution investigation. According to department documents, Morrissey was also accused of pressuring subordinates help him cover-up his activities.

Smith initially wanted Morrissey fired for the on-the-clock erotic escapades. When that failed, she sought to remove him as an instructor in the academy that trains incoming deputies, concerned that he might corrupt the new recruits. Rather than bar him as an instructor, Hirokawa, in his own words, pitched the idea of re-assigning him to the detectives unit because he was an otherwise diligent, well-liked employee.

“We had options,” Hirokawa said in the deposition. “We tried to come up with, let’s just say, alternatives for him.”

Hirokawa says in depositions that he was involved in meetings in which Morrissey would be reassigned as a detective. Hirokawa, by his own account, was also deeply involved in the discipline process that resulted in Morrissey’s demotion rather than termination.

After Morrissey was caught red-handed, not only did Hirokawa seek a good position for the accused voyeur and hookup advertiser, he participated in softening the disciplinary actions and expressed misgivings about Sheriff Smith’s treatment of him, which was viewed as politically motivated and personally vindictive.

Hirokawa praised Morrissey as “very energetic,” “engaged,” “a good communicator” and “level headed” in his deposition, according to documents received by San Jose Inside. Despite his misconduct, Morrissey was a favorite instructor, Hirokawa said, and should be allowed to teach cadets despite director orders to pull him out of the Academy.

He also testified that Morrissey’s discipline for porn-watching may have been “disproportionate” to the documented misconduct. Hirokawa suggested he felt the same about his discipline for failing to report hate speech about “kikes,” “nig nogs” and “cunts” sent by fellow officers because they have the right to say what they want on their own devices and in their own free time.

“What if the sergeant found out that a group of deputies had used disparaging slurs about racial ethnic groups or women, would you expect a sergeant to report that to a superior officer?” Deputy County Counsel Melissa Kiniyalocts asked Hirokawa during the deposition last fall.

“While they’re off duty?” Hirokawa inquired.

“Yes, well, on duty and off duty.”

“On duty more so than maybe off duty.”

“Why?”

“On duty we have on duty conduct,” Hirokawa explained. “Off duty—again, depending on the—let’s just say the stage or the context of what’s going on. Like, is this bantering? You know, it depends.”

“Do you consider prolific use of the N-word bantering?”

“Depends on the context,” Hirokawa answered, before clarifying that he personally doesn’t consider it bantering.

That’s a far cry from the press release he posted on his campaign website in July, which declared unequivocally that there’s “no place for hateful speech,” and the message he’s been telling his supporters ever since his public split with Morrissey.

Hirokawa did not respond to a request for comment on Morrissey’s recent resignation.