Sylvester
Leon returned to Jamaica with the Jamaica Choir and performed in their very
popular concerts which celebrated the Choir's return, in Kingston in January 1909.
His portrayal of Shylock from The Merchant of Venice was an instant
success. He quickly showed that he had not forgotten his roots, being involved
in two concerts in February, one for the residents of the Leper Home in Spanish
Town, the other for the Kingston Catholic Sodality Union. Later in the year he
appeared with the Choir in concerts all over the island, creating an immediate
reputation for his dramatic and humorous performances. He also did other
performances for specifically Catholic occasions, namely for the Mission in
Spanish Town and at Thomas Linton's Continuation School in Kingston which was
sponsored by the church.
After
a bout of illness in October Leon began to think of returning to England. He
took part in the Jamaica Choir's Christmas concert at Rockfort Gardens, and
then started on a series of performances in Kingston and around the island
which as the year progressed were billed as farewell performances. His
performances of extracts from Hamlet were particularly successful. He once again performed with the Choir
at Rockfort Gardens in its Easter Concert.

Soon
after this it was announced that he would be returning to England, probably on
May 19th. He started on a final round of farewell appearances in Montego
Bay, Spanish Town and Morant Bay as well as Kingston; he included the whole
range of his repertoire in these performances. The death of the king, Edward
VII, on May 6th led to a rearrangement of the schedule and the
postponement of his departure. After these very successful appearances,
Sylvester Leon left Jamaica, for the last time it would appear, on the 'Port
Antonio', on June 2nd 1910.