As the mother of three elite rugby players, Michelle Chessum – Company Secretary at Bailey Trailers and daughter of founder Tom Bailey – has watched what began as childhood enthusiasm for sport grow into careers at the very highest level.
Two of her sons now play for Leicester Tigers and have represented England on the international stage, with experience that has even extended to British & Irish Lions selection, while the third is following closely in their footsteps as part of the Leicester Tigers Academy. It is a remarkable family story, rooted in hard work, humility and unwavering support, values that feel right at home at Bailey Trailers.
Looking back, Michelle recalls that all three boys were introduced to sport at a very young age.
“They were around four when they started playing,” she explains, “mostly football and cricket at first.” At the time, there were no obvious signs that elite sport lay ahead. “I can honestly say I never thought they were naturals at either,” she admits, “but they enjoyed being outdoors, being part of a team and just playing.” What stood out wasn’t raw talent, but enthusiasm and competitiveness.
That early enjoyment shaped Michelle’s philosophy on children and sport, the key is enjoyment. “As long as they’re enjoying it, take them along come rain or shine,” she says. Michelle believes children should be encouraged to try a range of sports rather than specialising too early. “When they’re young, all they want to do is play,” she adds, stressing the importance of joining clubs where children get real game time. “Being a substitute week after week quickly loses its appeal.”
As the boys progressed and rugby became central to their lives, Michelle has found that watching matches brings mixed emotions. “At the start of a game I feel huge pride,” she says, “but that very quickly turns into anxiety.” From the fear of injury to worrying about their performance or disappointment, watching can be stressful. “I wouldn’t miss a game for the world,” Michelle admits, “but I rarely enjoy watching.” It’s a sentiment many parents of professional athletes will recognise, pride intertwined with constant concern.
Asked about her proudest moments, Michelle doesn’t point to trophies, caps or milestones, although there have been many. Instead, her pride lies in the men her sons have become. “They’re three great lads,” she says simply. “They’re spoken so highly of by so many people, and that makes me proud.”
Of course, professional sport comes with its share of injuries, Michelle is quick to identify who copes least well. “Oliver has always been the worst patient,” she laughs, “He’s not a very good patient and I’m probably not a very good nurse.”
What Michelle admires most about her sons now is their work ethic and resilience. “They are incredibly hard working and committed,” she says.
Playing professional rugby demands determination, especially when the journey isn’t smooth. “It would have been easy at times to give in, but they never did. They stuck at it.”
Oliver, the eldest, remembers his earliest sporting experiences vividly. Saturdays were spent playing cricket at Billingborough Cricket Club or football at Ancaster with his cousin Jazz. Rugby didn’t enter the picture until secondary school, when he was around 13. Lewis’s memories are similar, also rooted in Ancaster football club, although he jokes that being left-footed with two right feet didn’t necessarily help. Rugby only became an option once Oliver made the move to secondary school. “I thought I’d give it a go,” Lewis recalls, “and I enjoyed it.”
As their professional ambitions grew, both Oliver and Lewis faced moments of doubt. For Oliver, family support proved crucial. Coming from a sporty household with a cricket-playing dad and netball-playing mum, encouragement was never far away.
When Oliver realised he had a genuine chance of making rugby a career, it was Michelle who pushed him to seize the opportunity. “You’re not going to get a chance like this again,” she told him. The support of the wider Bailey family was also instrumental in driving Oliver forwards.
Lewis’s experience within the Leicester Tigers academy system tested his confidence. As numbers dwindled and competition intensified, self-doubt crept in. “I was convinced I wasn’t going to make it,” he admits.
Once again, Michelle’s encouragement played a key role, alongside Oliver’s example. Watching his brother recalled into the Tigers squad after playing for Nottingham became a powerful motivator. “It showed me it was possible,” Lewis says, “and it kept me pushing for a contract.”
Along the way both brothers have heeded important advice. Oliver’s centres on perspective: “Don’t listen to opinions from people you wouldn’t take advice from.” In the high-pressure world of professional sport, where scrutiny is constant, learning to filter out noise is essential. Lewis, meanwhile, credits his success to work ethic. “Don’t be beaten on effort,” he says, recalling school holidays spent working while friends relaxed. “If you really want something, you’ve got to work harder than anyone else.”
Those values extend into how both view team success. For Oliver, belief is fundamental. “If you don’t believe, there’s no point turning up,” he says, also citing perseverance and shared ambition, which turn good teams into formidable ones. Lewis highlights relentlessness in training, preparation and performance. “Every moment matters,” he explains. High standards, clearly set and consistently upheld, define top teams.
Both Oliver and Lewis have spent time working at Bailey Trailers, gaining first-hand experience on the factory floor. Oliver initially worked one day a week while playing for Nottingham, before moving into full-time work during Covid.
From operating machinery to welding drawbars and axles, he developed practical skills and a real appreciation for craftsmanship. “Welding is an art,” he says. “There’s a lot of satisfaction in getting it just right.” Lewis similarly worked across the factory, fitting lights, brake pipes and assisting with trailer repairs. For both, the key takeaway was the value of hard work and being willing to learn something new.
If rugby hadn’t worked out, Oliver believes he’d likely have joined the family business in some capacity, while Lewis says simply, “I’d probably be at Bailey Trailers.”
Dylan, youngest of the three is at an earlier stage of his rugby journey. Having only started rugby at 15, he was relatively new to the sport when he entered the Tigers Academy trials. Initially hesitant, it was Oliver and Lewis who encouraged him to take the chance.
Since then, Dylan has embraced the challenge, even adapting to a new position. “It’s been tough,” he admits, “but I’m loving it.”
When asked who the best player is among the three, Dylan laughs. He suggests it’s between himself and Oliver, describing Lewis as someone who has worked relentlessly for everything he’s achieved. “I’m really proud of both my brothers,” Dylan says. “They’re not just great players, but great brothers.”
Perhaps the simplest yet most telling insight comes when the boys are asked to sum up their mother in one word. Oliver chooses “rock.” Lewis says “relentless.” Dylan opts for “caring.” Together, they paint a constant presence, quietly driving, supporting and believing. Much like Bailey Trailers itself, a story of commitment, resilience and family at its core.
