For millions of sports fans around the world, major international tournaments like the FIFA World Cup and Olympic Games are defined by the thrill of victory, the agony of defeat, and the unforgettable action unfolding on the pitch or track. For Christopher Williams, a Jamaican business leader and former collegiate footballer, these events have always meant something far deeper: they are the foundation of a deliberate, 15-year family tradition built to heal past wounds and forge unbreakable bonds with his two sons, Zachary and Justin-Paul.
Raised in humble circumstances without the close, affectionate father-son connection he craved as a child, Williams, chairman and CEO of Different Properties Jamaica Limited and former head of Professional Football Jamaica Limited, made a promise to his own children early on: he would give them the intentional quality time and secure bond he never got to experience growing up. A lifelong lover of football, sports, and his home country Jamaica, Williams turned his long-held passion into the perfect vessel for this promise.
Fifteen years ago, Christopher and his wife Michelle made a deliberate choice to forgo accumulating material gifts for their boys, and instead opened a dedicated vacation savings account earmarked entirely for shared family experiences: opportunities to travel, laugh, learn, and celebrate together, one major sports event at a time. What started as a small, intentional plan has grown into a cross-continental adventure that has reshaped their family dynamic. To date, the Williams family has attended three FIFA World Cups – Brazil 2014, Qatar 2022, and the ongoing 2026 tournament hosted across the United States, Canada, and Mexico – alongside the Olympic Games, domestic Jamaican Premier League matches, and the 2023 UEFA Champions League final held in Istanbul.
Looking back on the 15-year journey, Christopher notes the quiet, moving transformation that has unfolded. When the tradition first began, his sons were small children entirely dependent on Christopher and Michelle to plan every detail of their trips, from transportation to accommodation. Today, the roles have shifted: it is Zachary and Justin-Paul who map out itineraries, book rides and hotels, and care for their parents throughout the journey. “It has been really moving for me as a father to watch them get to this level and be in charge of our experiential trips,” Williams shared in an interview with the *Sunday Observer*.
One beloved ritual has become synonymous with the Williams family’s adventures: the Jamaican flag never gets left behind. No matter if they are heading to a Champions League final or a World Cup opener, the iconic black, green, and gold standard is always the last item checked before they leave for the airport. “The last thing we say to each other before we leave for the airport is, ‘Yo, you pack the flag?’ ” Christopher said with a laugh.
This small tradition has led to countless unexpected, warm encounters with sports fans from around the world. During the 2026 World Cup’s opening match between hosts Mexico and South Africa at Mexico City’s legendary Estadio Azteca, Zachary and Christopher’s visible Jamaican flag drew crowds of spectators eager to say hello and snap photos. A 15-minute walk around the stadium took nearly twice as long, as the pair stopped again and again to greet new people. “It was maybe a 15-minute walk, and it took us about half an hour because of how many times we had to stop and take pictures,” 19-year-old Zachary recalled. “It was literally insane.”
For Christopher, attending that opening match at Azteca Stadium carried a personal, emotional weight that went far beyond the final score. He deliberately chose to attend the match because of the stadium’s iconic place in football history: it was here that Diego Maradona, his childhood hero, led Argentina to World Cup victory in 1986. Forty years after that legendary final, standing on the same ground he had only read and dreamed about as a boy, Williams called the moment overwhelming. “Growing up, I dreamt of that Diego Maradona final in 1986 in Azteca when Maradona won the World Cup, and to know that 40 years later in the World Cup we were in that stadium, tears come to your eyes,” he said. “As you’re walking, you’re looking at the pitch, you’re looking at the sun, and you’re just wondering what it was like 40 years ago when Diego won the World Cup, so it was very emotional for me.”
Each member of the Williams family holds their own treasured memory from the 15 years of adventures. Justin-Paul, 28, who was unable to attend the 2026 Mexico trip, counts the 2012 London Olympics as his most unforgettable experience, when Jamaica made history by sweeping the men’s 100m podium, led by sprint legend Usain Bolt. The entire family showed up decked out in Puma gear, the brand that sponsored Jamaica’s track team, leading event officials to mistake them for official team members. The happy mistake got them access to the field and a prime spot in the reporters’ booth to watch the historic race. “I remember how electric the stadium was before the men’s 100-metre final. Everybody was scrambling to get a good view. Then all that excitement went by in nine seconds. It was unbelievable,” he said.
For Zachary, who was born in 2006 – itself a World Cup year – the most memorable experience was an exhibition El Clásico match held in Miami, featuring some of the greatest footballers of a generation: Cristiano Ronaldo and Karim Benzema of Real Madrid, and Lionel Messi, Luis Suárez, and Neymar for Barcelona. “I remember almost every second of that game. Hearing the Real Madrid supporters singing before the match and seeing the players warming up right in front of me was surreal. The whole second half I stood on my chair. It was such a good experience,” he said.
Beyond creating shared memories, the family’s shared love of football has also sparked lighthearted, loving rivalry around the house. A lifelong diehard Manchester United fan, Christopher constantly teases Zachary over his support for rivals Manchester City. The friendly competition also extends to the pitch: Christopher and Zachary play frequent weekend matches, with the elder Williams still eager to prove he has not lost his touch. “Before I retired as a top baller, of course, I would buss up his salad every weekend,” Christopher joked, prompting Zachary to quickly interject “Not every weekend,” drawing peals of laughter from the whole family.
For all the iconic stadiums he has visited and historic moments he has witnessed, Christopher says fatherhood remains his greatest and most important life achievement. “It’s the last thing I think about at night and the first thing I think about in the morning, how my kids are doing mentally, whether they’re happy, and whether they feel they have a shot at building themselves in life. I don’t want to show them love through presents. I want to show them through my presence and by being there for them as much as possible,” he said.
That consistent, intentional presence has left a permanent mark on his sons. Zachary spoke openly about the impact of his father’s choice to prioritize shared experiences over work or material gain. “I would just like to tell my dad thank you again for making it such a priority in his life and making the sacrifices necessary. I’m sure it wasn’t easy, but it’s life-changing for me and my brother to be able to have these experiences. I love you, and I appreciate the sacrifices you’ve made,” he said.
Justin-Paul, who works alongside his father in the real estate industry, added that Christopher has not only been a father but a mentor, peer, and friend, creating a new model of intentional fatherhood that he and Zachary will carry forward to their own families one day. Because Christopher grew up without a positive fatherhood blueprint to follow, he built one from scratch for his sons. “When my brother and I have children we’ll have a blueprint, because he is the blueprint. It is great to have been raised by a king,” Justin-Paul said.
As Jamaica prepares to celebrate Father’s Day on June 21, Christopher says he hopes his family’s story will serve as a reminder for Jamaican fathers across the island that intentional, positive fatherhood is a powerful, lasting gift. “We just want Jamaica and everybody to know that we are present. We’re not going away. We’re staying in our children’s lives, giving them guidance, encouragement, support, and love,” the father of two said.