Article by Emanuel Giordano

The topic is always much debated, and the confusion due to the various oral traditions is great. Kyan sensei lived mainly in Okinawa and Tokyo, where he moved for a while to follow his father, a member of the exiled court of the former ruler of the extinct Ryukyu Kingdom, Sho Tai. To try to shed light on the subject, I will report below some written sources of the time (or immediately following), discarding oral and / or modern sources.
TAIDAN (1st PART),  24 SEPTEMBER 1957 
Nagamine: […] Who was under Itosu sensei?
Chibana: Yabu Kentsu (Sergeant Yabu), Hanashiro Chomo, Kyan Chotoku
(Chan Mi-gwa), Yamakawa Choto and Kina Choken were my senpai, Chinen, Mabuni Kenwa, Gusukuma Shinpan, Tokuda Anbun, etc, they were my dohai, but now I am the only survivor. There were also Motobu Choyu and his brother Choki, Yabiku Moden, etc..” 
According to what Chibana sensei wrote, Kyan sensei also practiced Karate under the guidance of Itosu sensei, although he cannot be referred to as his main teacher. As we will see later in the article, Kyan sensei himself declared that he had studied with several teachers, although he did not name them all. Moreover, like Funakoshi sensei, he too wrote that at the time it was customary to go to different teachers to learn their specialties! As we know from Yabu sensei (Itosu no buyuden, 1915), Itosu sensei's specialty was the Naihanchi kata, praised by Asato Anko sensei as the best execution of this form in all of Shuri and Tomari!
Kyan studied with Oyadomari from Tomari. […] His Kusanku kata originates from the lineage of Chatan Yara. He actually learned this kata from Yara of Yomitan, who was a direct descendant of Chatan Yara.
This written source confirms what is already known traditionally, that is, the origins of the peculiar version of the Kusanku kata handed down by Kyan sensei.
[…] and so my father, Chofu, made my daily routine fight with my older brother, Chohitsu, to make my body stronger.
Subsequently, as soon as I finished the ritual that marked my reaching adulthood on the day I turned 15 [1884. Kyan was born in 1870, but according to the Japanese method of counting the years of age, they don't start from 0 as for us Westerners, but from 1], my father stood in front of me and my brother and told us that we couldn't become real men if we didn't study martial arts. He said that from then on he would teach us the authentic martial arts.
As can be learned from this, Kyan began practicing the first rudiments of martial arts by fighting with his older brother (the second son) in order to strengthen the body. Later, after they turned 15, his father began to train them personally.
I will never forget the spring of my sixteenth year [1885], when I went to Shikina-en with my father and first met the famous Okinawan Karate master of the Restoration period: Matsumura Sokon. I was able to train with Matsumura sensei thanks to my father's introduction. I remember that Matsumura sensei was eighty [in reality he was 76 or, according to the Japanese counting method, 77]. I learned Karate kata from him, it was called Gojushiho, and I still practice this kata today, I have never forgotten it. […] I received instructions from Matsumura Sokon for two years and, little by little, I became interested in martial arts, more and more.
According to the above, Kyan practiced Karate with Matsumura sensei for two years, then from 1885 to 1887, although we don't know how often. He had to interrupt the practice to follow his father to Tokyo, who was a member of Sho Tai's court. Sho Tai was already in Tokyo since 1879, with 100 people in tow (including Asato Anko sensei), but in 1884 he returned for a short period to Okinawa for business reasons. In accordance with what Kyan wrote in the rest of the text, he and his brother followed their father shortly after his departure for Tokyo, therefore in 1887. Here we encounter an incongruity. Kyan declares that 5 years after his transfer to Tokyo, that is, around 1892, Matsumura sensei died, while according to the data of the Okinawa Prefecture (Monument to the Shuri-te), and according to the data present on his tomb (erected by the family ), he died in 1899, that is 4 years after Kyan's return to Okinawa. The date of death of Matsumura Sokon sensei is always a matter of discussion, and I believe that a thorough investigation should be carried out.
For family reasons I returned home to Okinawa when I was 26 [1895]. Upon my return to Okinawa I received Karate lessons from Matsumora Kosaku sensei from Tomari, Oyadomari Peichin sensei, etc. The instructors in those days, out of mutual respect, taught their students only their particular specialty. If a student asked his teacher to show him something that another teacher was well known for, [the pupil] would be introduced to that teacher to receive his teachings.
As can be seen from what has been written, on his return to Okinawa Kyan studied Karate with Matsumora sensei, Oyadomari sensei, and with other unspecified teachers. It is therefore possible that, if he also studied with Itosu sensei (as stated by Chibana sensei in Taidan, and by Nagamine sensei in his book Tales of Okinawa's Great Masters) he did so in this period. A further indication of his contacts with the latter master lies in the sentence below, also taken from the same article.
Matsumura sensei and Itosu sensei still hit makiwara when they were over eighty.” 
In addition to these teachers, Kyan sensei continued to make technical exchanges with various Okinawan teachers in the following years, also attending Gusukuma Shinpan sensei, in accordance with what Iha Seikichi sensei (Beikoku Shidokan Shorin-ryu) stated in a video shot in Okinawa in 2019.
Obviously there are also different oral traditions handed down by different students of Kyan sensei, and it is fair to remember that some of today's practitioners, members of the Kyan lineage, absolutely deny any kind of contact with Itosu sensei and his Karate, although several martial exchanges are documented with several students of the latter (interview with Iha sensei, Karate-do Kyohan by Funakoshi sensei, etc.), although Kyan sensei also took part in the spread of Okinawan Karate through performances, teaching in schools, etc., and although some sources written by people who lived at the time of the events (eg Chibana sensei) clearly report contacts between the two. However, for the drafting of this article I have chosen to base myself only on written sources, chronologically closer to the time of the facts, discarding the most modern sources which, according to myself, almost always suffer (regardless of the topic) from manipulation and attempts at revisionism (in its negative meaning).
In conclusion, written sources report that Kyan sensei began studying martial arts under the guidance of his father, Kyan Chofu. Subsequently he studied for two years with Matsumura Sokon sensei, from whom he had to separate to follow his father to Tokyo. On his return he studied with Matsumora Kosaku sensei, Oyadomari Kokan sensei, and with other unspecified masters including, perhaps in the same period, Itosu sensei, according to what was declared by Chibana sensei (and subsequently by Nagamine sensei). Finally, he also learned Kusanku from Yara of Yomitan. Obviously this with regard to Karate, and excluding the study of bo-jutsu, etc.
  • "Shorin-ryu Karate: kata 2" (here)
  • "Shorin-ryu Karate: kata" (here)
  • "Shorin-ryu Karate: The legacy of the bodyguards of the king of Okinawa" (here)
  • "The legend of the masters of Okinawan Karate: Biographies, curiosities and mysteries"  (here)