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WASHINGTON — The suspect charged in last month’s South Carolina church massacre should not have been allowed to purchase the weapon used in the attack, FBI Director James Comey said Friday as he outlined a series of “heartbreaking” missed opportunities and flawed paperwork that allowed the transaction to take place.

“We are all sick that this has happened,” Comey told reporters in an unusual, hastily scheduled meeting at FBI headquarters. “We wish we could turn back time, because from this vantage point, everything seems obvious. But we cannot.”

The cascading set of problems began with the drug-related arrest of Dylann Roof in South Carolina weeks before the June 17 shooting, which left nine dead. During that arrest, police say he admitted to possessing illegal drugs.

Under federal rules, that admission alone would have been enough to immediately disqualify him from his gun purchase even though he wasn’t convicted of the charge. But, Comey said, the FBI background check examiner who evaluated Roof’s request to buy a gun never saw the arrest report because the wrong arresting agency was listed on the South Carolina criminal-history records that she reviewed.

Had the West Virginia-based examiner seen the police report, the April purchase would have been denied, Comey said. The request was on hold for three business days as the FBI examiner sought information about whether it should be approved or rejected. Once that window closed, the firearms dealer used its legal discretion to allow the sale to be completed.

Comey said he learned about the problem Thursday night and had directed an internal 30-day review into the situation and the FBI’s background check process more generally. The Justice Department’s inspector general already had been exploring the same issue.

Sen. Chuck Grassley, the Republican chairman of the Senate Judiciary Committee, condemned the errors.

“It’s disastrous that this bureaucratic mistake prevented existing laws from working and blocking an illegal gun sale,” he said. “The facts undercut attempts to use the tragedy to enact unnecessary gun laws. The American people, and especially the victims’ families, deserve better.”

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