It was billed as the largest criminal indictment in Hawaii history.

The counts related to gambling numbered 414. Nine defendants. Nearly 80 sweepstakes machines seized.

The investigation spanned roughly two years, but pursuit of the charges unraveled in a matter of days.

A state judge last month tossed out the indictment, finding that the two deputy prosecutors who presented evidence to the grand jury committed prosecutorial misconduct.

And even though Judge Randal Lee dismissed the charges without prejudice, leaving the door open for a new indictment, he took the unusual step of disqualifying Deputy Prosecutors Katherine Kealoha and Jacob Delaplane from pursuing the case again.

The bungling of the grand jury presentation was the first of two recent high-profile missteps in cases involving Kealoha and her husband, Louis Kealoha, chief of the Honolulu Police Department.

A federal criminal complaint against Katherine Kealoha’s uncle, Gerard Puana, was dismissed earlier this month after the police chief inappropriately mentioned the defendant’s criminal history during testimony. That triggered a mistrial.

First Assistant Federal Public Defender Alexander Silvert, Puana’s attorney, has said the defense investigation uncovered police misconduct in the case against his client, who was accused of stealing the mailbox at the Kealoha’s former home. The allegations of police misconduct have been referred to the FBI.

Chief Kealoha has not responded publicly to the allegations.

While the mailbox case has intensified scrutiny on Kealoha and his department, the gambling case has magnified the spotlight on the prosecutor’s office.

Lee cited numerous discrepancies in Katherine Kealoha and Delaplane’s presentation to the grand jury but concluded that their misconduct was unintentional, due to a lack of experience with complex cases. Such discrepancies would not be expected from prosecutors with substantial experience in grand jury proceedings, he added.

Delaplane, however, told the Honolulu Star-Advertiser that since becoming a prosecutor in 2007, he has taken hundreds of cases to a grand jury, including racketeering and other complex crimes.

City Prosecutor Keith Kaneshiro likewise defended Kealoha’s experience, saying she has been with the prosecutor’s office for 10 to 20 years. Kealoha is on personal leave as head of the office’s Career Criminal Unit and was unavailable for comment.

The 77 sweepstakes devices were seized from six Oahu gaming parlors in September 2012. Prosecutors and police described them as illegal gambling machines. But the defendants argued the machines are legal.

Lee’s ruling portrayed a case that was mishandled in several ways, and he cited "troubling" testimony or actions by the two prosecutors.

After a two-year investigation that encompassed more than 20,000 documents, Lee said he was troubled that Delaplane was assigned to prepare the 414-count charging document even though he had been hired just two weeks earlier, acknowledged not reading the entire case file and couldn’t recall whether he reviewed the closing investigative report.

Delaplane was assigned to assist Kealoha, the lead prosecutor for the case.

The judge said he was equally troubled by Kealoha’s disregard of pertinent information related to ownership of several businesses named in the indictment, and by her failure to correct inaccurate testimony by two of the three witnesses called to testify before the grand jury.

The discrepancies included insufficient evidence and excessive use of hearsay, Lee concluded. Among other things, he cited:

» No evidence to demonstrate that the machines seized were the same machines played during the undercover investigation.

» No forensic financial accounting to prove that profits or deposits from the devices were gambling proceeds.

» Evidence that undermined the grand jury’s responsibility to determine whether probable cause existed to issue an indictment.

Kaneshiro said the lack of evidence cited by the court dealt with information that would be needed to prove a case beyond a reasonable doubt, not what was needed to establish probable cause — a lower threshold — for an indictment.

He also disputed Lee’s finding of prosecutorial misconduct, saying the judge based his ruling on an incomplete set of facts. Kaneshiro noted that Lee issued his ruling after a hearing to reconsider the court’s decision to dismiss the indictment.

No hearing was held specifically to review the grand jury proceedings or the qualifications of Kealoha or Delaplane, leading Kaneshiro to say Lee overstepped his authority in disqualifying the pair.

Kaneshiro also criticized Lee for taking "minor stuff and blowing it out of proportion."

Still, he said he would not take the judge’s findings lightly as his office plans to seek a new indictment.

Kaneshiro’s office filed the motion to dismiss the earlier case, acknowledging potential deficiencies it intended to address.

Bruce Green, a Fordham University law school professor in New York, said it is uncommon for a judge to dismiss a case without prejudice while disqualifying individual prosecutors from pursuing the case.

"That’s an unusual thing for the court to say," Green said.

But Green and Ken Lawson, an associate faculty specialist at the University of Hawaii law school, said after reading Lee’s ruling that they agreed with his decision to allow the case to be refiled. They said the prosecutorial misconduct did not appear to be egregious or intentional — the threshold required to dismiss charges with prejudice.

Myles Breiner, an attorney for Tracy Yoshimura, the lead defendant in the case, said prosecutors so bungled the grand jury presentation that the charges should have been dismissed with prejudice.

"It was such a hackneyed job," Breiner said.

The prosecutor’s office has also been criticized this year for a series of setbacks.

Prosecutors were unable to get a murder conviction in August at the second trial of federal agent Christopher Deedy, who fatally shot Kollin Elderts in a Waikiki McDonald’s restaurant in November 2011. Though Deedy was acquitted of second-degree murder, the jury was unable to reach a verdict on the lesser charges of manslaughter or assault, which means he can be tried a third time.

Kaneshiro’s office also took heat when it failed to file charges in a negligent homicide case before the statute of limitations lapsed and disclosed in November that it had discovered 15 to 20 sex assault cases that also were not pursued for the same reason. But Kaneshiro said the charging deadline for the latter cases expired before he took office.

More recently, a state appeals court overturned a Waipahu man’s manslaughter sentence because the prosecutor in the case urged the judge to impose a harsh penalty "to send a message to the Micronesian community." A defendant’s race is not relevant in sentencing.

Kaneshiro disputed the notion that the outcome of the Deedy trial was a setback.

"That’s the process," he told the Star-Advertiser in an interview. "It’s not really a setback because the jury couldn’t reach a verdict."

Kaneshiro noted that his administration had nothing to do with the lapses in the sex assault cases, and saved 30 others in which the statute of limitations was about to expire. He also said he personally apologized for his office’s failure to file charges in the negligent homicide case.

On the matter of the deputy seeking a harsher penalty for a Micronesian defendant, Kaneshiro said that attorney was disciplined. He called the courtroom incident an isolated one that wasn’t indicative of the good work done by his office.

Kaneshiro cited several tough-to-prosecute cases — including convictions for a 1989 murder of an elderly woman and a 2009 Chinatown killing in which two prior trials ended with no verdicts — as examples of that good work.

"There shouldn’t be any isolated incidents," Kaneshiro said. "But you know what, our world is not perfect. There are mistakes made. I’m not claiming our office is perfect."