SHORT ANSWER:
Yes. You are naive.
LONG ANSWER:
You are not a History teacher, are you?
When Jesus was preaching, Judea was a Roman province gained by Roman conquest of the region. Did you think that Jesus, the Apostles and the rest of the Jews of Judea at that time spoke Latin, the language of Rome, as their main language because Judea was a ROMAN TERRITORY?
Hong Kong was a British Crown Colony from 1842 until 1997, gained by British conquest of the region. Did you think that from 1842 until 1997, the residents of Hong Kong spoke English, the language of Great Britain, as their main language because Hong Kong was a BRITISH TERRITORY?
The Philippines were:
1. Spanish territory from 1571 to 1898, gained by Spanish conquest of the region.
2. U.S. territory from 1898 to December 1941, gained by U.S. conquest of the region during the same same Spanish-American War that made Puerto Rico a U.S. territory.
3. Japanese territory from December 1941 to October 1944, gained by Japanese conquest of the region.
4. U.S. territory again from October 1944 to July 1946, gained by U.S. reconquest of the region.
Did you think that the main language in the Philippines was Spanish from 1571 to 1898, English from 1898 to December 1941, Japanese from December 1941 to October 1944 and then back to English from October 1944 to July 1946?
No. The Filipinos continued to speak the local languages that their parents, grand parents and ancestors had spoken for hundreds of years.
Map of the dominant linguistic groups of the Philippines.
Puerto Rico has been a Spanish-speaking island since the early 1500's and the vast majority of Puerto Rican families have been native Spanish speakers for hundreds of years.
Expecting native Puerto Ricans to speak English as their main language in Puerto Rico simply because Puerto Rico is a U.S. territory is as naive as expecting Jesus, the Apostles and all the rest of the Jews in the Holy Land at the time to speak Latin as their main language simply because Judea was a Roman province.
Give the kid a break.
If Jesus had been sent to school in Rome by Joseph and Mary, one of His teachers could have been saying:
"Here is what I am trying to figure out. I have several students from Judea, a ROMAN TERRITORY, yet the main language is Aramaic or Hebrew. I have one student named Jesus who barely understands anything I say in the classroom. Maybe I’m just naive to think that the main language in a Roman Territory would be Latin."