From picking up rubbish for Martin Allen to coaching in Puerto Rico, Chesterfield's assistant boss has taken the road less travelled by

He took little convincing to become Martin Allen’s assistant at Chesterfield, thanks to their 24-year long association. It was Allen who set Whitbread on the path to his current career. “I played with him when I was at West Ham, then followed each other to Portsmouth,” he said. “He used to run soccer schools and I used to go help and pick up the rubbish, look after the place. “Martin finished playing and I was still playing, because I’m a bit younger than the gaffer. “He went to Reading and they took me on loan, so I had two very successful years on loan at Reading with him where he was coach. “I retired and Martin was then the manager of Barnet for the first time at Underhill. “I didn’t know what I was going to do post-football and that was when I really started my education in coaching.” Whitbread’s first steps into the coaching game were far from glamorous, but he credits them with helping shape the coach he is now. “Martin took me under his wing and I learnt how a football club works from top to bottom. “It wasn’t just a question of come in, coach, go home. “It was come in, do the kit, do the balls, do the bibs, do the discs, wash the water bottles out, get ready for training and that’s where we’ve kind of been. “It’s great having people to do all the jobs but you have to learn to do them all to grow as a coach and a manager. “I’m sure it won’t be any different here.” Whitbread calls Allen a leader and insists the move to Chesterfield did not have to be sold to him. He’s never been shy of taking on a new challenge, as his coaching CV proves. In 2008 he moved across the world to become Puerto Rico national team assistant and also take on the number two role with the Puerto Rico Islanders. Since then he’s been head coach of the Islanders, managed Antigua Barracuda FC, Bahrain Under 23s and become the first ever head coach of Puerto Rico FC. His career went full circle when he linked up with Allen again at Barnet late last season and now they’ve arrived in Chesterfield to try and halt the club’s slide. “I think it’s what we’re all about, a challenge,” he said. “It’s obviously been a difficult time for Chesterfield, but it’s got a fantastic man in charge now at the helm to give the club a push in a different direction to where they’ve been going. “The challenge is to turn around and be playing for a promotion. “Two relegations in the last two years is never a good thing, that’s the one thing we don’t want next season. “I’m ready to bed down, I’m moving up here to be part of it and hopefully part of a successful time.”