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If Loretta Sheehan had her way, Honolulu Police Chief Louis Kealoha would be prepping for a fight to keep his job rather than cashing a $250,000 check.

Sheehan was the only Honolulu police commissioner to vote against a lucrative retirement deal Wednesday that allowed Kealoha to resign in “good standing” despite the fact he’s the target of an ongoing U.S. Justice Department investigation into public corruption.

Unlike her colleagues, Sheehan wanted to begin termination proceedings against Kealoha, which under city law would require the police commission to present the chief with a written statement outlining the reasons he should be fired. He would then be able to refute those allegations at a hearing before the commission.

“I voted against the agreement because I believe it’s expensive, unnecessary and very likely undeserved,” Sheehan said Wednesday.

She unsuccessfully argued her case during a closed-door commission  meeting that lasted nearly four hours. Sheehan presented the other commissioners with the draft of a letter to be given to Kealoha laying out various charges that she believed warranted his removal as the head of the 20th largest police department in the country.

The document, which Sheehan provided to Civil Beat, makes only passing reference to the Justice Department’s ongoing criminal probe into Kealoha.

That investigation includes numerous suspects and stems from allegations that Kealoha and his wife, Katherine, a supervising prosecuting attorney for the city, had framed her estranged uncle for stealing the Kealohas’ mailbox with the help of several Honolulu Police Department officers, one of whom has already pleaded guilty to felony conspiracy.

Instead, Sheehan said in the letter, there have been numerous other examples of questionable decision-making and lax oversight that she believed warranted the chief’s removal.

“Generally, the reasons involve your failure to demonstrate the leadership and managerial qualities essential to the position of Chief of Police, including failure to investigate, correct and prevent misconduct by officers you supervise,” Sheehan wrote.

Her letter addressed 11 concerns, including dwindling morale in the department, excessive use of force, Kealoha’s candor during police commission meetings, his lack of response to the need for cybercrime training and HPD’s struggles in addressing domestic violence, particularly in the police force.

Many of the issues were the topic of previous meetings at which Sheehan asked pointed questions about the department.

State Sen. Will Espero said he would have supported Sheehan’s efforts to hold the chief accountable for problems within his department. Espero has been an outspoken critic of HPD and the chief on many of the issues Sheehan addressed in her letter.

But he said there were still many other concerns that came up while Kealoha was chief, including destroyed and unprocessed rape kits, delays in providing updated crime-mapping statistics to the public and concerns about a cheating scandal at the police academy.

He also noted that HPD fired a record number of police officers in 2015 for misconduct and criminal behavior. The department might say that shows that it has gotten tougher when it comes to discipline, Espero said, but it’s merely a reaction to growing public pressure and legislative actions. He said he’s skeptical that the department would have changed course on its own.

“I believe there was a strong case for termination,” Espero said. “Loretta is a breath of fresh air and she’s providing a perspective and insight that’s been lacking on the police commission. Hopefully it will be contagious and we will see more debate, more transparency and more accountability within the department.”

Specifically, Sheehan wanted details about Kealoha’s decision in February to promote Maj. Ryan Borges to assistant chief despite his history of domestic violence. Borges’ promotion, which did not go through, was seen as a tone-deaf maneuver considering that the department was already under intense scrutiny for mishandling domestic violence cases.

Sheehan also wanted more details about Kealoha’s response to numerous incidents that have resulted in high-profile legal settlements that have cost city taxpayers millions of dollars.

One case in particular involved allegations by current and former officers of systemic racial and sexual discrimination within HPD that resulted in the permanent disability of at least one officer, who said she did not receive proper backup. The case settled for $4.7 million, but the city also paid out nearly $1 million in legal fees to outside law firms to defend itself.

Another case Sheehan was interested in involved two hikers who said they were brutalized by HPD officers who mistook them for burglars. The hikers received a six-figure settlement from the city, but the incident raised questions about whether Kealoha and HPD were letting the individual officers off the hook.

The police commission, which is the sole independent oversight entity for HPD, initially found that some of the officers involved had used excessive force against the hikers, one of whom suffered fractured bones in his face during his arrest.

Despite the commission’s findings, Kealoha defended his officers’ actions and refused to discipline any of them.

The lack of discipline has been a concern for Sheehan, not only in the case involving the hikers, but also in the racial discrimination lawsuit. One of the police officers accused of using racial slurs against his fellow officers had been recommended for suspension but Kealoha overturned that decision.

In the letter, Sheehan, a former city and federal prosecutor, requested numerous documents that would help her build a case against the chief, including those related to internal affairs investigations, surveys of officer morale and travel records for retired Deputy Police Chief Marie McCauley, who Kealoha sent to an FBI leadership training event despite the fact that she was planning to leave the department.

Sheehan said she would use the subpoena power voters granted to the commission in November to get access to those documents.

Sheehan, who is out of state, was unavailable to comment on her proposal to the commission.

Police Commission Chairman Max Sword, who generally speaks for the commission, did not return a phone call seeking comment.

Steven Levinson, who has been one of the more open and accessible people on the police commission, didn’t want to discuss any of the specifics of the backroom discussions that led to the chief’s retirement deal.

But the former Hawaii Supreme Court associate justice said he struggled when weighing the options, including Sheehan’s suggestion to initiate termination proceedings.

“I thought then and I think now that the commission would have been in a strong position had the commission decided to take the termination route,” Levinson said. “Nevertheless, had we ultimately opted to go to the mattresses with the chief there very likely would have been civil litigation resulting from it.”

Levinson’s decision to approve the settlement came down to a cost-benefit analysis. He said he presumed the chief would file a lawsuit no matter the outcome of the commission’s termination proceedings. That case, he said, would likely go on for years, possibly even going to the Hawaii Supreme Court.

Considering the financial and emotional toll, Levinson said it was better to pay the chief to retire and drop any future legal claims he might make.

“It really was a tough decision for me because I think it was a close call,” Levinson said, noting that he has 37 years of experience of negotiating settlements in legal conflicts. “In an ideal world essentially all civil disputes should settle. If they didn’t then somebody wasn’t doing their job or was being unreasonable.”