The teenager striker, who will be hoping to follow in the footsteps of his dad, Danny, has been with the Owls academy for a good few years now, climbing up the ranks from the U9s to his current position of being offered a two-year scholarship.
And he’s certainly grasping the opportunity, scoring a hattrick for the U18s over the weekend in a big 5-1 win over Ipswich Town that his old man would’ve been proud of.
Speaking to The Star, the youngster’s dad – a former Owls youth coach himself – gave some insight into the youngster, saying, “He’s a young U16 – he’s not 16 until May… It’s great for him, and physically he can cope because he’s quite a big boy for his age. It’s nice experience for him.
“He had a bit of comedown on the journey back from Ipswich because the bus broke down! But we messaged on the bus and the following day we had a look through the game. It’s been a decent week for him.”
But it wasn’t always easy, with some parents believing that – as a kid – Bailey was only there because of his dad’s involvement. That myth has since been dispelled as he continues to impress and play numerous games above his actual age group.
Cadamarteri Snr explained, “I was aware of other parents that were saying that he was only there because I was the U18s manager, and I think the most beneficial thing for him was when I left to go to Burnley – and he was still there.
“He started to get a bit more credit for his own performances then, rather than people thinking it was because of me. He started to get more recognition, and I do think it’s difficult for kids when their parents have a history or background.”
And Bailey’s not the only little Cadamarteri zipping around the fields of Middlewood Road, either, with his younger brother, Caelan, currently doing his thing with the U11s.
It’s been a while since their dad left the club, now, but with a number of young players having progressed nicely through the ranks at Hillsborough, there’s definitely a pathway to success that the former Sheffield United striker played a part in forging.
The ex-Everton man helped in the development of the likes of Alex Hunt, Liam Shaw, Liam Waldock and others, and he’ll no doubt be excited to see the good work still being done by Steve Haslam and his team – work that is contributing to Bailey’s rise.
Wednesday’s young forward did cause a bit of grief for his dad not long ago, though, when he bagged four goals for SWFC’s U16s against Sheffield United – Danny’s current employers.
“Just before he was offered his scholarship he scored four against Sheffield United, which made a few ripples,” he said. “But it didn’t help me because I’m working there! So I was getting a bit of jip for that.”