Even as Hong Kong media tycoon Jimmy Lai looks to defend himself against possible charges under China’s national security law, a long-running feud with a rival tabloid may see him end up in jail.

Lai’s trial for "criminal intimidation” in 2017 of a reporter from the Oriental Daily News, a fierce competitor to his flagship Apple Daily, is set for closing arguments on Friday. If convicted, he faces as many as five years in prison. Lai has pleaded not guilty.

The case is the first among at least five faced by Lai, one of Hong Kong’s most influential democracy advocates who has loudly criticized Beijing’s push to clamp down on dissent in the city. After his Aug. 10 arrest under the national security law — unrelated to the Oriental Daily case — about 200 police officers searched the headquarters of his media empire, Next Digital Ltd., and seized multiple cartons of documents. Lai said the arrest was based on "trumped up” allegations.