The Winchester family: A calling to every continent

Greg and friends on the Appalachian Trail at McAfee Knob in Virginia

In 1989, Greg Winchester was given a book about two American businessmen who had climbed the seven summits – the highest peak on each continent. At the time, he and his wife, Jan, were raising two kids (four more would eventually join the family), and he was the executive vice president of one of the largest commercial real estate lenders in the country.

As a nature-lover and hiker, Greg was inspired, but he knew a year-long trip around the world, not to mention the training required, was not in the cards. “I would have liked to climb all seven summits on seven continents,” Greg says. “But there was no way with family obligations at home and a demanding commercial finance career.” 

That’s when a missionary couple from Nepal came to speak at Greg and Jan’s church. Nepal was just opening up to the gospel, and the couple was starting a school there. A spark of inspiration was ignited within both Greg and Jan – a desire to leave a mark on each continent, not by climbing mountains, but by supporting charities on each continent, not only financially, but also as volunteers and trusted advisors. 

Not knowing where to start, they kept their ears and eyes open for opportunities. They knew this calling was a big one, and it would take decades of divine inspiration and leaps of faith to achieve.

Jan at the dedication of the pastor training center (Pastors Discipleship Network) in Kampala, Uganda

The adventure begins

God presented the needs quickly on the first three continents. In South America, they supported an orphanage in Bolivia and a ministry for displaced indigenous people in Venezuela. 

In Asia, they provided aid for a missionary couple who served in both Bhutan and India as well as a charity focused on offering education services to rescued victims of sex trafficking in Nepal.

In Africa, they were initial patrons of a pastor training center and a Christian university in Uganda. They also supported a sustainable Christian orphanage and school which offers vocational training in Zambia.

Although they looked for giving opportunities in Europe, nothing rose to the surface. They were almost ready to give up on the continent when Greg went on a pilgrimage to Winchester, England on recommendation from many friends and work colleagues in both the US and the UK. While there, he visited the Winchester Cathedral and came across an exquisite piece of medieval artwork – the Winchester Bible. 

Made in the 12th century and passed down through the years to many different individuals, this historic Bible was in need of repair and restoration. The cathedral was starting the costly and tedious work of preserving this beautiful biblical text. 

“They were creating a museum where half a million people a year would be visiting and would see this Bible and the amazing illustrations and hear the story of the founding of England,” Greg says. 

Moved by this initiative and the opportunity to bring the message of Christ to millions of travelers in a unique and beautiful way, Greg and Jan began supporting the restoration of volume four of the Winchester Bible. They’d found their purpose in Europe. 

Greg in the Winchester Cathedral with the 4th volume of the fully restored Winchester Bible

And to the ends of the earth

Shortly after, a similar calling arose in Antarctica. Determined to find a way to reach even the most remote corners of the earth, Greg learned about a picturesque church on South Georgia Island off the coast of Antarctica called the Whalers Church

He contacted the South Georgia Heritage Trust to see if they had any needs and discovered they had multiple projects planned. The trust needed funds for an item at the church and a special exhibit at the museum next door dedicated to Antarctic explorer Sir Ernest Shackelton. 

Today, the exhibit welcomes thousands of ecotourists and shares the story of Shackleton’s Christian faith and how it carried him and his men through his polar exploration. 

Like Antarctica and England, the right organizations in Australia were elusive at first. Then, through Redeemer City to City, the Winchesters discovered initiatives to help rebuild and replant churches throughout Australia and New Zealand. 

Honing in on a plan for their giving

By the early 2000s, the Winchesters had thrown their net wide. The idea of giving on every continent in the world was inspiring and fun. And although they saw patterns in their passions, giving was starting to feel overwhelming. That’s when they were introduced to NCF. 

Greg and Jan with the crow’s nest from Sir Ernest Shackleton’s ship in London, England

“I was helping run a business that I co-owned with my two partners. We had six kids, middle school through college. It was a busy time,” Greg says. “I found, through my tax advisors and accountants working with NCF, some ways to do things that have allowed us, frankly, to increase our level of giving.” The Winchesters love giving through NCF because they can save on taxes and give more to charity.

With the help of Boyd Bailey who leads the NCF team in Atlanta, the Winchesters were able to pinpoint four causes where they wanted to focus their giving: cities, schools, media, and conservation.

“Having those four cause areas has been very helpful to us,” Greg says. “That doesn’t mean every now and then we don’t do something else, but in terms of who we’re really serious about giving money to, it has to fit in one of those buckets.”

NCF also introduced the Winchesters to TrustBridge Global Foundation, an organization that makes global giving to foreign charities and organizations simpler and more efficient. “We have a lot of recurring gifts that relate to ministries around these continents plus in the United States, and it’s just made it a lot easier transactionally,” Greg says. 

Some of the foreign charities the Winchesters work with, like the Winchester Cathedral in England, have begun using TrustBridge as well. Greg says, without NCF, he never would have known how to find TrustBridge. “Jan and I are wired for adventure,” says Greg, “and the biggest adventure of our life is the one the Lord has taken us on with our global generosity mission.”

The Winchester family

Creating a legacy of giving

In 2017, Greg and Jan began hosting Journey of Generosity events (JOGs) to encourage others to listen for God’s inspiration in their own lives. To date, they have hosted nearly a dozen JOGs and inspired others to host many more all over the world. 

In their own family, they’ve established a Christmas tradition of gathering to decide on charities and causes for their year-end giving. Each of their six children chooses a handful of organizations whose work speaks to their individual passions, and, together, they learn and give. 

“Dad wants us to pick something that’s meaningful to us,” says the Winchesters’ oldest daughter, Mary-Elsye. Like her nature-loving father, Mary-Elsye is very involved in the care and conservation of the beautiful trails surrounding her Colorado home in the Vail Valley. 

Greg and Jan are grateful for this gift of a better understanding of their children’s hearts. Their passions and volunteer work that may have otherwise gone unnoticed or unspoken come to the surface in a beautiful way during this family gathering.

Their oldest son, Dustin, cherishes this time. “When we’re together as a family and everybody brings up the different charities, you can see where everybody’s different priorities are, where their hearts are, and that brings us closer together.”

Continuing to leap

The Winchesters have faithfully followed God’s promptings on the journey of a lifetime, one they could have never dreamed of or planned themselves. They say it hasn’t always been a matter of simply saying “yes” to the opportunities God presents. In fact, it is rarely simple at all. 

“It’s a struggle, it’s a battle,” Greg says. “And then all of a sudden, you feel confirmation, and it’s a leap of faith. Each one of them has been a leap of faith because it never makes sense.”

“I guess the point of all this is a lot of joy, a lot of adventure,” Greg says. “A lot of unexpected things come about that you never anticipate. And that’s what’s been so wonderful about it.” It’s that sense of adventure that keeps the Winchesters leaping. And it’s the joy that drives them to bring others along on the journey. 

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