Free Issue! Try Saltscapes Magazine before you buy. Download Now

In 1940, Herring Cove was a small, Irish-Catholic fishing village on the rocky shores near the entry to Halifax harbour. Although fewer than 500 people lived in the village, almost all of Halifax’s harbour pilots came from there or nearby.

Just before midnight on March 28, 1940, as villagers slept, the most tragic disaster ever inflicted on Herring Cove was unfolding just a few kilometres out at sea, at the mouth of Halifax Harbour.

It was about 11:30pm, a cool clear night, about -2 Celsius, with a calm sea. The inbound Newfoundland-registered freighter Esmond had just rammed and sunk the pilot boat Hebridean. Nearly a dozen men were struggling in the freezing ocean, pleading for rescue.

Survivor Carl Himmelman clung to a hunk of wood, which was the difference between life and death for him, as he recounted when he spoke to a Halifax Mail reporter from his hospital bed.

“I was ready to give up when I saw the boat coming. That gave me courage. I could hardly control myself for the numbness but I was able to hold out.” 

His shipmate and fellow harbour pilot Roy Sullivan found a life buoy but had given up hope, he told the same reporter.

“I didn’t know a man could have so many thoughts in such a short time. I really never expected to be picked up. It looked like the end.”

It nearly was. As hypothermia was about to finish them off, Sullivan and Himmelman, dressed only in their underwear, had their numb, near lifeless bodies hauled into a lifeboat launched from the very vessel that had torn into and sunk Hebridean. They’d been in the icy waters for close to 20 minutes.

Historic disaster

Himmelman and Sullivan just survived the worst disaster in the 230-year history of the Halifax harbour pilot service. Nine others aboard the Hebridean, including six pilots, couldn’t hold on. An unnamed man in the rescue boat told a Halifax Herald reporter that moments after they picked up Sullivan, they could see another man in the dark struggling. “We almost reached him. He disappeared. We don’t know who he was.” 

That night, Hebridean and Esmond, with its 5,000-ton cargo of newsprint, had a scheduled rendezvous beyond the mouth of Halifax Harbour so that pilot Tupper Hayes could board the freighter. A harbour pilot’s job is to safely guide ships into and out of port. That night, it was the 98-ton Hebridean—with a pilot at the wheel—that became the deadly hazard.

Around 11:20pm, Hayes and boatmen Walter Power and Edward MacLaughlin left the Hebridean in a tender to row to the Esmond. Most of the 11 men left on the pilot boat were below deck. Some, like Himmelman and Sullivan, were asleep in bunks.

Pilot James Renner was in charge of the Hebridean because its regular captain, Nicholas “Mont” Power, left an hour earlier to guide another ship into Halifax. It was early days in the Second World War and a convoy was being assembled in the harbour. More ships were expected overnight, which is why there were so many pilots aboard the Hebridean.

Only minutes after Hayes and the boatmen left in the tender, the Hebridean was impaled on the bow of the 128-meter Esmond and the pilot boat was sinking fast. Men were dying, trapped in the wreck, or struggling in the sea.

Within 36 hours, Admiralty Court Justice William Carroll was heading an investigation behind closed doors to find out how the collision happened. Wartime censorship sealed details of the collision so that ship movements in and out of Halifax were not revealed.

Testimony from pilots Himmelman, Sullivan, and Hayes, as well as from Esmond’s captain, James Davitt, were crucial. However, James Renner’s fateful final decision or the problem that led to the collision remains a mystery. Pilot Renner was among the nine who perished.

Hebridean was a wooden hulled schooner, rigged with sails and launched in Mahone Bay in 1928. It also had a diesel engine, which it was using that night. Sullivan testified that on two previous trips, the engine stalled and there was difficulty with it because of suspected fuel line problems. The pilot boat was equipped with a wireless radio, but it wasn’t working that night so there was no communication between the two vessels. Curiously, the Hebridean routinely put in at nearby Herring Cove, its home port, three times a night—but for some reason that night, it didn’t.

A deadly mistake

Witnesses testified that when Hayes and the boatmen left in the tender for the freighter, Hebridean was about 400 meters and 45 degrees off the Esmond’s starboard bow. That would be on the right side of the Esmond, looking from the bridge to the bow. Although, its engines were stopped a few minutes earlier, Esmond was slowly making way at a speed that Hayes said pilots preferred when boarding a ship.

Once Hayes and the tender were clear, Hebridean’s engine started, the pilot boat turned, and made ready to cross in front of the freighter. However, Renner did not set a course at right angles to the freighter, which would have given plenty of time to safely cross. He set the Hebridean at a sharp angle, pointing toward the inbound freighter coming in from almost the opposite direction. Esmond’s captain, James Davitt, speculated that Renner probably wanted to cross over and quickly pick up Power, MacLauglin and the tender after Hayes was aboard the Esmond. Davitt was astonished at the very risky manoeuver to get to the other side of his ship. Then, about 100 meters from Esmond, Hebridean’s engine abruptly stopped for a few moments. Now it was safe only if Hebridean stayed put.

Suddenly, Hebridean’s engine flashed up again and still at the same sharp angle to the Esmond bow, the pilot boat made a last desperate scramble to cross in front of the Esmond.

Hayes watched helplessly from the tender and testified, “When I looked around and saw they were going across,
I thought they were getting so close there would be something happen.”

On the bridge of the Esmond, Davitt was in disbelief and later testified, “When he gets underneath my starboard bow, he is going at a considerable speed. I don’t know whether the tide caught him or what happened, but he come slap hard into my stem…” 

Esmond’s steel bow tore into the Hebridean’s wooden hull about midships. Below deck, it smashed a hole in the side where pilot Lionel Pelham would have been sleeping, and at the foot of Himmelman’s bunk. Electrical power was cut.

Himmelman and Sullivan clawed their way through the dark in their underwear and in bare feet, water rushing up to their knees, scrambling up to the deck. Renner was there, as well as brothers James and Carleton Dempsey and their cousin Lorne Dempsey, all pilots. So was deckhand Roy Purcell and pilot Claude Martin. Pilot Lionel Pelham, engineer Mathew Power, and cook Lawrence Thomas didn’t make it from below. The life jackets were also below deck.

Desperate efforts to launch the lifeboat were defeated by a wall of water pouring against it and over the deck. The wreck was simultaneously being pushed through the ocean by the freighter and quickly sinking beneath the feet of the men struggling for their lives. Sullivan later said, “There was no excitement at all. Everyone seemed surprisingly calm.”

In the dying seconds, men jumped, were pushed into or swallowed by the icy sea beside the freighter towering over them. As it was going down, Himmelman got tangled in the rigging and from his hospital room, later said, “I felt the suction pulling me down. I kept going down.
I was never so far underwater in my life.”

It was over in less than two minutes. Hebridean sank like a stone. 


Altar display of the Hebridean and victims at March 2022 Memorial Mass in Saint Paul church in Herring Cove. 

A community changed forever

Within an hour, families knew. Gloria Dempsey says she was told by her mother-
in-law Elsie that, “They were awakened by the noise and somebody pounding on the door and they knew then. They knew something had to be wrong.” Her husband Carlton was dead. She was a widow with seven sons, the eldest 15, and another on the way.

Almost all the men were from Herring Cove or had lived there and were related in one way or another. Left to mourn them were eight widows and 38 children. Among the three Dempsey families, there were 26 left fatherless. Roy Purcell never saw the daughter his wife gave birth to the night before. A hard road lay ahead; there was precious few social programs back then. Mostly they depended on family and on one another.

Lorne Dempsey lost both of his grandfathers that night, Lorne and James. He says his grandmother, Dora told him,
“It was a difficult time for all the widows financially…pensions for their husbands were very small.”

Carleton Dempsey’s grandson, Stephen, says his father, Larry who at 15 was Elsie’s oldest, ended his schooling that night. Stephen says, “He went to work at [Canadian National] at the ripe old age of 15.”

The tragedy was never discussed within the families. Stephen said it would be raised only during the annual Remembrance Mass at St. Paul’s Catholic church in the village. Stephen says, “I mean, there was sorrow. There didn’t seem to be any sense of, you know, how hard done we were. You just got on with it.”

Three hours after the sinking, pilot boat number 1, Nauphila, with crew and pilots replaced Hebridean on station. Tupper Hayes, Edward MacLaughlin and Walter Power were on the job the next day. It was early days in the Second World War and there were hundreds of more ships expected in Halifax.

After a week in the Halifax Infirmary, Carl Himmelman told a reporter, “I don’t know when I’ll get back to work but they are so shorthanded, I expect they’ll want all they can get. It’s hard to think about it. There were a lot of fine men on that boat.”

Lessons learned

Just two weeks after the sinking, in April 1940, Justice Carroll submitted his report to Transport Minister C. D. Howe.
In it, he absolved
Esmond’s captain, James Davitt, of blame. Carroll, at first, placed all guilt on pilot boat captain James Renner and wrote, “…the captain in charge was guilty of an error in judgement in attempting to cross ahead of the Esmond.” In the very next sentence he exonerated Renner, writing, “That personal error of judgment may be erased if the engine of his boat stalled while crossing, and he not being aware of any fault therein.”

Carroll recommended that new regulations be imposed on pilot boats prohibiting them from passing in front of ships when transferring pilots and requiring there be life jackets and a life raft on the decks of pilot boats. He also suggested inbound ships have an officer on the forecastle to monitor a pilot boat’s position.

The bodies of the nine men were never recovered. There is a headstone in the St. Paul church cemetery with the names of all nine on it. The church was central to life in the village and parish priest Father J. C. McKinnon knew them well. The morning after, the grief-stricken pastor told a reporter, “Lorne Dempsey was like a son to me. In fact, I called him ‘my boy.’ But they were all fine men.”

There’s a plaque on a church altar with the names of each of the men and every year a mass is celebrated on the anniversary of the tragedy for the men lost. Descendants still attend to remember and pray for them.

In 2010, on the 70th anniversary of the tragedy, the Atlantic Pilotage Authority established a small park near the breakwater at the head of the cove where the pilot boat used to tie up. In Hebridean Park is a monument with the image of the boat and the names of the men lost.

Pilot boats still put in there occasionally but there are no pilots from Herring Cove anymore

Other Stories You May Enjoy

Nostalgia for bricks and mortar

There’s no magic for children in online shopping

Our Search and Rescue volunteers

Not your average hike in the woods 

Hallowed Ground

Bill Piers and other kids who grew up in the 1950s along the inlet in Halifax Harbour called the Northwest Arm had heard the stories and the warnings. Stay off Deadman’s Island. Strange lights were...