A serial killer convicted for murdering three men in 2001 is appealing his death sentence and continuing a 16-year challenge to avoid execution.

In January a federal jury in Massachusetts sentenced Gary Lee Sampson, 57, to die for the 2001 carjacking and murder of Jonathan Rizzo, a 19-year university student, the Boston Globe reported.

The killer has also received a life sentence in Massachusetts for killing 69-year old plumber Philip McCloskey and in New Hampshire for slaying Robert Whitney, his third victim.

He tricked Rizzo and McCloskey into giving him a ride with a car and then fatally stabbed both men after he directed them to a hidden area. Later, he strangled Whitney with a rope, the Globe reported.

Sampson’s lawyers filed a notice of appeal against the death penalty on Monday following an unsuccessful request to toss the death penalty earlier this month.

His legal team is arguing that Sampson was brain-damaged when he fatally stabbed McCloskey and Rizzo.

The request to not execute Sampson was earlier denied by a U.S. District Court judge, Leo T. Sorokin, who said in his ruling that the killer will not be sparred as he “brutally and incomprehensibly murdered Philip McCloskey, Jonathan Rizzo and Robert Whitney.”

Sampson has been fighting to avoid execution for many years – he was first sentenced to death in 2003. The ruling was reversed following an appeal, but it prompted a second trial where the defendant pleaded guilty. A federal jury reached a decision to sentence Sampson to death again in January.

If the court dismisses Sampson’s appeal, he could take the case to the U.S. Supreme Court.

The Associated Press contributed to this report.