Boston Public Schools has asked a federal judge to dismiss a $5 million lawsuit filed by a former student who a high school dean shot in the head four years ago.

The city of Boston, acting on behalf of the school department, says the plaintiff, Luis Angel Rodriguez, is trying to hold the city liable, even though the shooting “occurred off of school grounds, after school hours,” and the dean’s "actions were unquestionably outside the scope of his employment.”

The dean, Shaun Harrison, shot Rodriguez in Roxbury in 2015 after the two began dealing drugs at the English High School in Jamaica Plain. At the time, Rodriguez was a sophomore there.

Rodriguez survived and in January sued Boston Public Schools in U.S. District Court, charging the district had been negligent in continuing to employ Harrison after he threw an object at a female student years before the shooting.

That incident happened while Harrison was working at Boston Green Academy in Brighton. He was dismissed from that school, then transferred to Orchard Gardens Pilot School in Roxbury and later promoted to an administrative position at English High, where he met Rodriguez.

Read More: Boston Public Schools Face $5 Million Lawsuit From Former Student Shot By Dean

The city claims “any connection between Harrison’s transfer and promotion and his decision to shoot Plaintiff is too tenuous” to support a claim against the city.

The city also argues Rodriguez failed to make his claim within two years of the shooting, as a state law requires.

The motion cites that law: “A civil action shall not be instituted against a public employer ... unless the claimant shall have first presented his claim in writing to the executive officer of such public employer within two years after the date upon which the cause of action arose.”

In his complaint, Rodriguez claims school officials “covered up [Harrison’s] criminal propensities by transferring him within the Boston Public School system,” and says that the district's alleged negligence led to “severe emotional distress, psychiatric injury, facial scarring, facial paralysis, hearing loss and other injuries.”

Harrison was indicted on Apr. 24, 2015 and convicted on May 31, 2018. He is currently serving 23 to 26 years at MCI-Cedar Junction.