A U.S. cit­i­zen who moved his fam­i­ly to Syr­ia to join the Is­lam­ic State ter­ror­ist group has been sen­tenced to 20 years in fed­er­al prison.

Em­raan Ali, 55, a U.S. cit­i­zen born in Trinidad and To­ba­go, was sen­tenced Tues­day in Mi­a­mi fed­er­al court, ac­cord­ing to court records. He plead­ed guilty in No­vem­ber to con­spir­ing to pro­vide ma­te­r­i­al sup­port to a for­eign ter­ror­ist or­ga­ni­za­tion.

Ac­cord­ing to court records, Ali moved his fam­i­ly from Trinidad and To­ba­go to Brazil, and then to Turkey and even­tu­al­ly Syr­ia in March 2015. He false­ly told his chil­dren that they were go­ing on va­ca­tion but ac­tu­al­ly in­tend­ed to join IS, pros­e­cu­tors said.

Af­ter ar­riv­ing in Syr­ia, IS reg­is­tered Ali and his fam­i­ly, and Ali un­der­went IS re­li­gious and mil­i­tary train­ing with oth­er Eng­lish speak­ers, of­fi­cials said. The train­ing in­clud­ed in­struc­tion on the op­er­a­tion of var­i­ous au­to­mat­ic weapons such as the AK-47 as­sault ri­fle and PKC ma­chine gun.

Ali was even­tu­al­ly dis­charged from com­bat du­ty and worked in res­i­den­tial con­struc­tion for IS in the group’s then-de fac­to cap­i­tal of Raqqa, in­ves­ti­ga­tors said. Ali al­so be­came a mer­chant and be­gan buy­ing and sell­ing live­stock, cars, weapons, weapons ac­ces­sories and tele­phones to and from oth­er IS mem­bers. Ali al­so pro­vid­ed mon­ey re­mit­ting ser­vices to oth­er Trinida­di­an IS fight­ers in Syr­ia and do­nat­ed his own mon­ey to IS mem­bers to sup­port the IS cause.

Ali and his fam­i­ly re­lo­cat­ed with­in Syr­ia sev­er­al times over the years, of­fi­cials said. Ali and his son, 22-year-old Ji­had Ali, sur­ren­dered to Syr­i­an De­mo­c­ra­t­ic Forces near Baghuz in March 2019, dur­ing the last sus­tained Is­lam­ic State group bat­tles to main­tain ter­ri­to­ry in Syr­ia, of­fi­cials said. They were lat­er trans­ferred to FBI cus­tody and re­turned to the U.S. The son, who was born in New York and be­gan IS mil­i­tary and re­li­gious train­ing at 15 years old, was pre­vi­ous­ly sen­tenced to five years in prison.

De­spite their de­feat in Syr­ia in March 2019, the mil­i­tant group’s sleep­er cells still car­ry out dead­ly at­tacks in both Syr­ia and Iraq where they once de­clared a “caliphate.”