The 11-year-old East Taieri School pupil has won the Mitre 10 Takahe Rescue Kids Art Competition with his artwork - one of more than 5000 entries in the national competition.
And no-one was more surprised than Bailey.
It was the first time he had entered an art competition and, until now, the only paintings he had done were to stick on the refrigerator at home.
"I was so surprised - it was so unexpected.
"Mum knew I had won but she was trying to keep it a secret so I could be surprised in school assembly when they announced it.
"When the Mitre 10 people turned up, I thought I might have been in with a chance."
Now, he is looking forward to shouting his family an all-expenses-paid Takahe Wilderness trip to Te Anau with Department of Conservation (Doc) rangers as hosts.
The trip includes a helicopter ride into the highly protected Takahe Valley in the Murchison Mountains and the unique opportunity to help feed tiny black takahe chicks as they grow in the safety of their brooder pens at Doc's Burwood Breeding facility.
Judge, Northcross Intermediate head of art Mark Jensen, said Bailey's painting was "distinctive".
"It shows an exploring, inquisitive takahe in an unusual and difficult perspective for a young artist to capture.
"The composition is well balanced and the paint technique is accomplished, using strong colouring and with skilful over-painting used on the tussocks in the landscape."
Bailey's Inquisitive Takahe will now feature in a calendar alongside other artworks which were short-listed in the competition.
It will be sold in Mitre 10 stores nationwide to raise funds for the Mitre 10 takahe rescue project.