FOR Christopher Williams, the FIFA World Cup, Olympic Games, and other major sporting events are about far more than the action on the field; they are opportunities to strengthen the bond he shares with his sons Zachary and Justin-Paul and create memories across continents that he hopes will last a lifetime.

From cheering in packed international and local stadia to proudly waving the Jamaican flag among thousands of spectators, the father and sons have turned their shared love for sports into a tradition that brings them closer with every event.

For Christopher, these experiences carry special meaning. Having grown up in humble circumstances without a close father-son relationship, the chairman and CEO of Different Properties Jamaica Limited said he made a promise to give his own children the connection and quality time he wished he had as a boy.

A former chairman of Professional Football Jamaica Limited (PFJL) and a former footballer for his alma mater, Jamaica College, Christopher said his passion for football, sports, and Jamaica runs deep, interests he has proudly shared with his sons.

He told the Jamaica Observer that 15 years ago, he and his wife, Michelle, decided to invest not in material gifts, but in a vacation savings account dedicated to creating experiences that would allow them to laugh, travel, learn, and celebrate together as a family.

Since then, they have attended three World Cup events: the 2014 World Cup hosted by Brazil, the 2022 World Cup in Qatar, and now the 2026 World Cup under way in the United States, Canada, and Mexico. Chris added that they have also attended the Olympic Games, local Jamaican Premier League matches, and even the 2023 Champions League final in Istanbul.

“When we started this process, Michelle and I, they were dependent on us, and they were babies, so we had to plan everything. We had to make sure every aspect of the trip was taken care of. Fast-forward 15 years later, and they are the ones planning the trips, booking the Ubers, taking care of us and making sure we have dinner, booking the hotel, everything. 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,” Christopher told the Sunday Observer.

Zachary Williams (left) and his father Christopher Williams raise the Jamaican flag at the 2026 World Cup opening match featuring host country Mexico and South Africa, in Estadio Azteca in Mexico City, Mexico.

One tradition that has become synonymous with the Williams family is carrying the Jamaican flag wherever they go. Whether at the Olympics, a World Cup match, or a Champions League final, the black, green, and gold flag is always packed before departure.

“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.

He said the decision has led to countless memorable encounters.

Zachary, the younger son, recalled that on their most recent trip they went to Mexico for the opening World Cup match between Mexico and South Africa. The match ended with Mexico securing a two-goal victory over South Africa. The 19-year-old said the stadium was electric with thousands of spectators supporting their country. Yet it was he and his father who took the spotlight when people, having seen the Jamaican flag, rushed over to say hi and take a picture.

“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. There was maybe a 10-minute span where the only thing we did was take pictures. We would stop, take a picture, and then somebody else would come take a picture. It was literally insane,” he recalled.

For Christopher, attending the World Cup match at Mexico City’s iconic Azteca Stadium carried a significance that went far beyond football. He said he deliberately chose that match because of the stadium’s rich history and its connection to Argentine legend Diego Maradona — one of his childhood heroes.

“I had spoken about [that match] a lot while they were growing up, so for him and for me, it was very emotional. 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. 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,” said Christopher.

While he was not able to make the Mexico trip, a 28-year-old Justin-Paul said one of his fondest memories with his dad was attending the 2012 London Olympics, where Jamaica dominated the male 100m event to clinch a 1-2-3 victory led by sprint legend Usain Bolt. He recalled that the family was outfitted in Puma gear that made officials mistake them for participants in the event, a mistake they capitalised on to gain access to the field and watch the race from the reporters’ booth.

The Williams family (from left): Justin-Paul, Michelle, Christopher, and Zachary, are decked in Jamaican colours while displaying the Jamaican flag at the 2022 World Cup final in Qatar.

“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.

Zachary, who was born in 2006, a World Cup year, points to an exhibition El Clásico match in Miami as one of his most treasured experiences. Featuring football icons Cristiano Ronaldo, Karim Benzema for Real Madrid, and Lionel Messi, Luis Suárez, and Neymar for Barcelona, the match left a lasting impression on the young football fan.

“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 told the Sunday Observer.

While football has created countless memories, it has also sparked friendly rivalry in the Williams household. Christopher, a loyal Manchester United supporter, regularly exchanges banter with Zachary over his allegiance to Manchester City. Christopher said he has also taken his sons to many local football matches and is not afraid to get in on the action. He said he and Zachary often play intense matches on the weekends as he tries to show him that, despite his age, he is still a baller.

“Before I retired as a top baller, of course, I would buss up his salad every weekend,” Christopher joked. “Not every weekend,” Zachary quickly responded, drawing laughter.

For all the stadia visited and trophies witnessed, Christopher insists that fatherhood remains his greatest 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.

The impact of that presence was evident when Zachary took a moment to thank his father.

“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,” said Zachary.

Justin-Paul added that it has been a blessing to have his father in his life as a mentor, peer in the real estate world, and even friend. He also credits his father for creating a blueprint for fatherhood.

“We can reason more openly, and there isn’t that shyness because, oh, he’s my father, I don’t want him to know this. Whatever it is, we can just talk about anything, and there is no sense of judgement there or anything,” he said.

“A lot of this he had to figure out first-hand. He didn’t have a blueprint from his father. 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,” said Justin-Paul.

As Jamaica marks Father’s Day on June 21, Christopher said he hopes his family’s story serves as a reminder that positive fatherhood remains alive and well across the island.

“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,” said the father of two.