Jim Callahan 1958 – 2026
An appreciation by Tomas De Vargas Machuca, Chairman HERO-ERA
American Jim Callahan a renowned and talented financial expert, sailor, historic car adventurer and family man whose zest for life endeared him to all around him, prematurely passed away on the 1st of January. The loss of Jim has shocked both the international financial and sporting communities, his demise has produced great sadness but elicited wonderful memories of a dynamo of a man.
Tomas De Vargas Machuca became close friends with the enthusiastic historic motorist and remembers the genial character who embraced the sport with passion.
“You know, we all have expressions, but Jim’s was, ‘it's all good.’ Whatever question you asked him, ‘it's all good,’ even though he'd had a long hard day on one of our endurance events, trying to fix a misfire or fiddling with a flat tyre for hours, his approach was always, ‘it's all good,’ and if it wasn’t, he’d find a way to make it that way!
“He became loved by everybody in the historic rally community, because he was just that guy who always had a smile. He was always going up to people to see whether he could help, or just see whether anybody needed help. He was there, but he wouldn't intrude either, but you'd know that if you needed help you could ask him, and the answer would always be yes to make it all good, just like his mantra.
“His premature passing, obviously came as a huge shock, not only to me and the HERO-ERA family, but to the wider community who met him on rallies, on the tours and of course, all of his family and friends back in the US. This is a huge loss for everybody who knew him and our thoughts, friendship and care, both motoring and non-motoring, go towards Jim, Dancia and their beloved family.
“HERO-ERA met Jim Callahan in 2023 on the Novice Trial where he came down with his good friend Bill Cody and hired our BMW 1602. He was eager to learn more about rallying, being a genuine Petrol Head himself, specifically more on prewar Bentleys. At the same time, he was looking to see what type of cars were going to transport his friends and family around the world for adventure.
“All I can say is that we hit it off like a house on fire, mainly as we'd had similar banking careers and career path in terms of that financial world, to this very day we still have some common friends. But the most incredible of coincidences is that he lived some 500 yards away from where my mother grew up in Greenwich, Connecticut. So every day he'd walk the dog and pass by my grandparent’s house where my mother had grown up, so clearly that created a much closer relationship.
“Within a month, we were now speaking on a daily basis. After Novice Trial, Jim came down and rented one of our Arrive Drive cars so that he could go rallying with his son. So in experience building events like the Flying Scotsman, I took Jim’s wife Dancia as my navigator because they'd already committed to the Peking to Paris Motor Challenge as a couple. This was going to be something they were going to do together, but Dani needed to learn more about navigation.
“By the time of the P2P, they became a team of three with Jim at the wheel and half of the event navigated by their son Tucker Rose, the other half by Dancia.
“We did the Scotsman twice, in the sense that he did the Scotsman with his wife, and then the Scotsman again with his car as a pre cursor to other events he was going to do with the Bentley which was being totally restored. Then Jim hired our Prodrive Mustang to tackle the Peking to Paris which he successfully completed, an accomplishment of which rightfully, he was extremely proud.
“He and Dancia had their entry booked for the Badawi Trail to the Last Oasis to explore the Middle East this year in their Bentley Speed Six. Far from being cancelled, it is with great courage and motivation that Dancia fully intends to take on the challenge in the Bentley, moving from the navigator’s seat to take over in the driver’s seat and compete, in her words; ‘to keep Jim’s memory and his aspirations alive.’ Jim would have been delighted that the adventures will continue and I’m sure he will be keeping a close watch.
“Jim participated in our Itineris Tour in Provence, and then we added a tour within the tour! We drove from the UK taking in as many mountain passes as we could so he could get fit enough to compete on the Badawi with his Bentley Speed Six, and trust me, hairpins in the heat with a big truck of a Speed Six are not exactly the easiest things to do!
Jim was looking at our new Gaucho Trail in South America, he was so enthusiastic about competing that he was looking at other events from now on until effectively he couldn’t drive any more! He was going to keep a couple of cars in the UK with us, with which he would rally around the world, and obviously keep the ones in America. Plans were all laid.
A prominent sailor, a member of the New York Yacht Club, a gentleman, a professional banker, he was a person who made his career as being Mr. Independent. He was involved in big debt arbitrages, and he had the respect of the entire international financial community, whether it was government or private funds. Jim Callahan was the go to guy, because his impartiality and his objectiveness was paramount.
He was great company, his easy style was a key part of any camaraderie on event. Together with Dani and Tucker Rose, we all had a lot of fun together exploring the world and enjoying historic motoring as a group. Jim and I became very close, but it was not just our love of the same passions of sailing and historic cars, we also shared the same general outlook on life and values.
It is very hard to believe that the wonderful relationship with Jim has ended, sadly before time, he was so young in that sense. We hope Dani may be with us on more events in the future, but if she is, we know that Jim will be riding right alongside us and when we come across the first obstacle he will just say; ‘It’s all good.’
James Callahan Obituary
James "Jim" Callahan
March 23, 1959 - January 1, 2026
James "Jim" Callahan, a true Renaissance man whose intellectual curiosity, generosity of spirit, and passion for life inspired all who knew him, passed away unexpectedly, of natural causes, on January 1, 2026. He was 66 years old.
Jim graduated from Ohio Wesleyan University, with a BA in Theater/Economics, and from the NYU Stern School of Business, with an MBA. Jim's professional accomplishments were remarkable, yet they represented only a fraction of what made him such a cherished husband, father, mentor, and friend.
Jim built his illustrious career at the intersection of financial innovation, institutional integrity and corporate governance, pioneering new markets while later becoming one of Wall Street's most trusted advisors. Jim began his career as a senior trader and banker on Wall Street, where his expertise and judgment earned wide respect. In 1995, Jim founded PentAlpha Global Advisors, an industry leading financial data and supervisory services firm dedicated to complete independence.
Jim was a trusted advisor to many U.S. financial regulators and government commissions. His consistent message: economic growth comes through reliable, responsible lending, not financial engineering. Even after four decades in finance, Jim never stopped evolving. From trader to banker, risk manager to entrepreneur, crisis advisor to system architect, Jim continued to invent, believing that it was his obligation to design systems that protected financial markets from the next crisis or breakdown.
Throughout his life, Jim served as a mentor to countless young professionals. These mentees often said that learning from Jim was like playing with a brilliant chess champion; Jim made you smarter every day.
Jim was awarded numerous U.S. patents for innovations related to the autonomous supervision and cash-flow optimization of distressed financial instruments. Jim's most enduring professional legacy may be the infrastructure he built at PentAlpha Surveillance, which delivers oversight and advice to hundreds of billions of dollars of debt products across corporate, consumer and project finance sectors. Jim believed the most important innovations are the ones you never notice-because they quietly make systems stronger.
Beyond his professional life, Jim found deep joy in pursuits that reflected both his intellect and his sense of adventure. An avid Yachtsman, he served as Commodore of American Yacht Club from 2013-2014, AYC Board Member, 2005-2014, and Lifetime member of the New York Yacht Club. His sailing achievements are too numerous to mention, but include yacht racing successes both inshore and offshore. Jim was awarded AYC Yachtsman of the Year in 2010.
With his beloved wife and closest companion, Dancia, at his side, Jim came tantalizingly close to circling the globe-whether guiding a sailboat across oceans or driving a classic car along distant roads. Nothing brought Jim greater happiness than sharing these passions with Dancia and their sons, Tucker and Winston Rose, whose love, laughter, and companionship filled his days.
Among Jim's proudest achievements was completing the six-week, 10,000-mile "2025 Peking to Paris Motor Challenge," driving a 1967 Mustang across deserts, mountain ranges, and remote borders. Jim cherished this once-in-a-lifetime experience, sharing it with one of his sons, Tucker, and his beloved wife, Dancia, his co-pilot in all of life's adventures.
As a passionate fly-fisherman, Jim traversed the globe, exploring some of the world's most stunning waters. Despite his skill in the sport, Jim's humility and humor always shined through. When asked, "How's the fishing?" Jim would always respond, "The fishing is great. The catching...not so good." He was a fixture in the Jackson Hole One-Fly Tournament and Foundation, having forged dozens of friendships along the way and, where only a few months ago, he and his team competed for their 25th consecutive year.
Jim's enthusiasm during annual shooting trips in the English countryside was evident to all. But Jim also held a deep appreciation and profound respect for those who worked to maintain the British countryside and its traditions. Jim was a true custodian of rural life, both its community and sportsmanship.
Jim spoke with pride and joy of being the father of five children: Tucker, Winston, Brooke, Lindsay and Caitlin.
For the past thirteen years, he was the devoted husband and best friend of his wife, Dancia; and their boys, Tucker Rose and Winston Rose, who will forever miss his warmth, kindness, generosity, and boundless zest for life.
Jim is survived by his wife, children, his brother and trusted confidant, John Callahan, and John's wife, Susan Callahan.
Jim Callahan was taken far too soon, but will be remembered for the grace with which he lived, the passions that drove him, and the enduring impact he left on his beloved wife, family, friends, and all who were fortunate enough to know this remarkable man.
In lieu of flowers, please consider making a donation, in memory of Jim Callahan, to Kids in Crisis, 1 Salem Street, Cos Cob, CT 06807, www.kidsincrisis.org .
Published by Greenwich Time from Jan. 11 to Jan. 12, 2026.
