Sir John Swan was remembered as a man who overcame obstacles by building connections and speaking to the heart.

Hundreds of mourners including dignitaries, family and friends filled the Cathedral of the Most Holy Trinity to bid farewell to Bermuda’s longest-serving premier in a ceremony planned by Sir John.

The Right Reverend Nicholas Dill, the Anglican Bishop of Bermuda, told attendees that Sir John had delivered specific instructions over the past year “refining and refining and refining”.

He added: “It was his intention that this service should reflect at some level his Anglican roots at St Monica’s Church and a desire to make it available to all who wanted to participate, but not overly formal and not too long.”

The ceremony featured prayer and song, including Ronnie Lopes performing Frank Sinatra’s iconic My Way.

David Burt said that it may never be known how many people Sir John helped and described him as a man who believed in people and was willing to extend himself to match the vision and drive of others.

The Premier added: “No difference in political position or ideology can diminish the miracle that a boy from Friswell’s Hill became the man who strode confidently to Front Street and held sway in the highest office for an unequalled 13 years.

“Beyond Front Street, this man of such humble beginnings courted queens and presidents along with lawmakers and CEOs, earning their respect and their friendship.

“He often took to driving GP1 himself — so much so that it is said on one occasion the actual diplomatic driver had to explain to someone why he was driving John Swan’s car.”

Mr Burt said that he could not imagine how long it would take Sir John to walk a single city block, because he always had time to hug everyone and take a moment to ask about their families.

He said that Sir John left a legacy of leadership.

“What cements John Swan’s legacy in the history of Bermuda is that he was always at the cusp of change, even before others knew change was in the air,” he added.

“His 13 years as premier was marked by significant economic and social changes in Bermuda and defined a generation and beyond.”

Malcolm Brock told the congregation that Sir John was able to connect with everyone he met because he spoke to people’s hearts.

Dr Brock recalled Sir John telling him about his time studying in West Virginia in the 1950s before the civil rights movement.

He said: “He was, as he described himself to me, a pond dog. A Bermudian, an islander, surrounded by Appalachian mountaineers who had never met anyone quite like him.

“So what did Sir John do? He told them stories. Stories about Bermuda, about its pink beaches, its turquoise waters, its white roofs, its people, its rhythms.

“He charmed his way, story by story, into the hearts of West Virginia families who invited this island boy into their homes for Thanksgiving.”

Dr Brock said Sir John used the same approach of connection negotiating the US-Bermuda tax treaty, finding in the Bermuda Archives the original letter from George Washington thanking the island for its help in the revolutionary war.

He said that Sir John presented the letter to Ronald Reagan in the Oval Office and stated: “Mr President, the people of Bermuda are here to collect on their debt.”

Dr Brock said that the president told the premier he needed to convince Congress and he had found that the main opposing politicians were from West Virginia.

In another tribute, Mitchell Blaser said that Sir John told him that he had sold the Majority Leader of the US Senate on the plan by playing into his love of Shakespeare, highlighting the connection between the discovery of Bermuda and The Tempest.

Mr Blaser added: “Real genius and the stuff of legends.”

He said that Sir John was driven by his unwavering belief in the people and potential of Bermuda.

Mr Blaser said: “Listing his accomplishments is not the way he would want to be remembered.

“Sir John was a towering figure not because of what he accumulated but by the relationships that he built.

“Everyone here, no matter what their background, they have been inspired by him. He loved everyone, and he was loved in return.

“As a leader, his purpose was clear: to motivate and inspire, to rise above the limitations and improve the community and take Bermuda to a higher level.

“As a man, his purpose was just as clear: to be the best father, to be the best role model, to be the best family man that he could be.”

David Dodwell told the gathering that Sir John was a multifaceted man who engaged with everyone he met and made a positive difference to them.

Mr Dodwell said: “He broke through those normal barriers and truly connected and made each one of us feel special.”

He said Sir John overcame many challenges to become one of Bermuda’s most significant leaders, placing the island on the international map.

Mr Dodwell added: “He counted world leaders from presidents to world-renowned business people as personal friends.

“We were all charmed by him, we were all engaged by him and we all felt richer for having known him.”

In addition to the hundreds in attendance at the Cathedral, others viewed the ceremony remotely at Pier Six and the Earl Cameron Theatre in City Hall.

Sir John, a successful businessman and the island’s longest-serving premier, passed away at the age of 90 this month.

He became premier in 1982 and led the United Bermuda Party to victory in three subsequent elections: October 29, 1985, February 9, 1989 and October 5, 1993.

His time as premier ended two weeks after Bermudians voted against independence by a vote of 16,369 to 5,714 in an August 1995 referendum.