Confessed mass shooter Nikolas Cruz had no criminal record despite dozens of disciplinary infractions, but there was one case in which Broward County school administrators were obligated to send him before a judge — and didn’t do it.

After trashing a middle-school bathroom in 2013, Mr. Cruz received a three-day referral to a newly created diversion program called Promise designed to help kids who had committed misdemeanors avoid arrest and stay out of the “school-to-prison pipeline.”

He didn’t show. At that point, school policy dictated that he should have been hauled before Judge Elijah Williams of the Broward County Delinquency Division, and yet there is no record that it ever happened, based on what the district has released, according to Timothy Sternberg, a former assistant principal who helped run Promise from 2014-17.

“There’s possible negligence here if no one ever followed up,” Mr. Sternberg told the Washington Times.

Since the deadly Feb. 14 school massacre in Parkland, Florida, Broward County officials have been accused of creating a lax disciplinary climate in their drive to reduce suspensions, expulsions and arrests, an environment that allowed Mr. Cruz to act out for years without serious consequences.

Files obtained by the Orlando Sun Sentinel show that Mr. Cruz committed 58 infractions from 2012-17 at Westglades Middle School and Marjory Stoneman Douglas High School, even though he was enrolled in 2015 at another school, Cross Creek, for students with emotional and behavioral disorders.

After nearly every episode, Mr. Cruz received the same type of punishment — detention, an in-school suspension or out-of-school suspension for one to three days—which also went against district policy.

A repeat offender like Mr. Cruz should have been brought before the district’s Behavior and Intervention Committee to decide “whether this student is appropriate for another setting,” Mr. Sternberg said.

“When you look at the discipline data, it’s not progressive,” said Mr. Sternberg, who sat on the committee. “It’s a one-day [suspension], and then he does the infraction again, and he gets another one-day. There’s no progression of discipline whatsoever.”

As a result, “With the child, it does create a false sense of ‘I can do this and nothing’s going to really happen to me,’ ” he said.

The district was lambasted after reversing its story on Promise, admitting last week that Mr. Cruz was once referred to the counseling-intensive program even though superintendent Robert Runcie had insisted for months that he wasn’t.

The district also said that Mr. Cruz underwent the intake process on Nov. 26, 2013, at Pine Ridge Education Center, but that he did not complete the program.

For Mr. Sternberg, the problem wasn’t that Mr. Cruz was referred to Promise—the problem is that district failed to follow its own rules.

“There was a breakdown in communication,” said Mr. Sternberg, who arrived after the Cruz referral. “Normally, when a student doesn’t complete the program, the district is supposed to tell the school, which then refers him to Judge Williams, but it doesn’t appear that ever happened.”

Under the protocol, the judge first tries to convince the student to participate in the program, an approach that usually works.

“They’re sitting in front of the judge, and the judge tries to reengage the student, telling them that, ‘If you don’t go to Promise, you have to go before the state’s attorney and further criminal action will take place,’” said Mr. Sternberg. “And 95 percent of the time, the student goes back into the program.”

Even if Mr. Cruz had refused, he would have at least landed on the juvenile-justice radar.

“He would have had some kind of contact with law enforcement,” said Mr. Sternberg. “Whether or not he would have been arrested—it’s discretionary always with law enforcement. Sometimes they’ll arrest you, sometimes they’ll give you a warning. But the school would have had the responsibility pre-Promise to call the police on that incident to report it and file a police report.”

Critics have pointed out that if Mr. Cruz had a criminal record, he would have been barred from purchasing the AR-15 used in the shooting at Stoneman Douglas, which left 17 dead.

Broward County schools declined to comment, saying the district continue to review Mr. Cruz’s disciplinary record and noting that an independent firm is also investigating.

“Rather than speculate about the possible reasons for his not returning, we feel it’s important to wait until we have the facts associated with his specific circumstances,” said the district in a statement.

Mr. Runcie was on the cutting edge of the Obama administration’s 2014 guidance warning schools to reduce racial disparities in discipline or face a civil-rights investigation, which has prodded hundreds of school districts to reduce their suspensions, expulsions and arrests.

Education Secretary Betsy DeVos is reviewing whether to rescind the directive amid complaints about rising school chaos from parents and teachers.

Even before the shooting, Mr. Sternberg, who left his job at the district’s Pine Ridge Education Center last year, had been urging the school board to investigate the “broken” disciplinary system.

While Promise has come to symbolize for some parents the district’s disciplinary failures, Mr. Sternberg continues to support the program, saying it provides resources to disruptive students with dysfunctional families that they might not otherwise receive.

“If Nikolas Cruz had gone through the program, he would have at least met with that counselor and gone through the DAP [Developmental Assets Profile],” he said. “They may have looked further into his home background. He would have gotten definitely another level of support.”

Ryan Petty, whose 14-year-old daughter Alaina Petty was killed at Stoneman Douglas, said the problem in Broward County schools is bigger than Promise.

“Students need a second chance. They need another opportunity, and I think that’s the intention of the Promise program,” Mr. Petty told the Miami New Times. “I think the issue is the overall discipline policies within the school district.”

Of course, even if the school system had followed its own protocol with regard to Mr. Cruz, there’s no guarantee it would have changed anything.

“Who knows whether what happened would have happened,” Mr. Sternberg said. “But at least he would have seen somebody else.”

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