
The giant manta ray fishermen: standing (left to right): Mart Lewis, Jack McCann, Charlie Willis, Roland Phillips and Gus Rice. Seated: Teddy Roosevelt and Russell Coles. From Scribner’s Magazine vol. 62, #1 (July 1917).
This is chapter 11 of Shark Hunter: Russell J. Coles at Cape Lookout.
Teddy Roosevelt left his home in Oyster Bay, New York, on March 23, 1917 and headed south to join Russell Coles and his crew of fishermen from Morehead City, N.C. to fulfill his dream of killing a giant oceanic manta ray.
He boarded a train in New York City and arrived in Punta Gorda, Florida, two days later, around noon on March 25.
There he rendezvoused with Coles and their guide, “Capt. Jack” McCann, as well as the seasoned crew of fishermen that Coles employed when he was living on his houseboat at Cape Lookout, N.C.
That crew included Capt. Charlie Willis and two other hands with whom he had worked for more than a decade, Roland Phillips and Mart Lewis.
Coles also brought a young businessman from Danville named A. A. “Gus” Rice, to help cook and do a variety of odd jobs at the camp.
(The Charlotte News in Charlotte, N.C., where Gus Rice worked, later published his account of the trip.)
The group of seven caught passage on one of the Punta Gorda Fish Company’s boats and traveled 30 miles to the east side of Captiva Island, a barrier island on the Gulf of Mexico.
There they found their camp, a scow anchored on the sound side of the island. The accommodations were spartan, but adequate: the boat had one deck and the cabin was just a single large room with bunks, a camp stove and gear. Capt. Jack’s skiff was tied to the scow.

Teddy Roosevelt posing with harpoon in the bow of Capt. Jack McCann’s flat-bottom skiff. Photo courtesy, Walter Coles, Sr., Chatham, Va.
In an article in Scribner’s Magazine (a copy of which my daughter Vera and I found at Coles Hill), Roosevelt later described Coles’ crew.
“All four were professional fishermen, averaging 50 years of age. They were alert, weather-beaten men who all their lives long had wrought their livelihood by hard and hazardous labor on the sea. They were quiet, hardworking, self-reliant, utterly fearless.”
Capt. Charlie Willis impressed him deeply. Roosevelt wrote:
“Tall Captain Charley Willis had been Coles’ boat companion for twelve years, was equally at home with sails and a gasoline-engine, and was a natural leader of men. He was a skilled, two-handed harpooner.”
Roosevelt found virtues in Roland Phillips as well.
“Little Roland Phillips had worked in Charley’s crew for nearly 30 years as second in command. He was as hard as iron and as quick as a cat, a skilled two-handed harpooner and an extraordinary lookout…. He interpreted with instant sureness every swirl or stain on the water and every dim shadow beneath it.”
Capt. Willis’s other longtime crewman was Mart Lewis.
“Tall, silent Mart Lewis had served under Charley for some 15 years; he was fisherman, engineer, cook—a first-class all-around man.”
None impressed Roosevelt more than Capt. Jack McCann though.
“Captain Jack McCann . . . was a little man, quiet-mannered and steel-eyed, whose reputation was that of being gentle with all well-behaved people and dangerous to all others.
“For over 30 years he has fished along the Gulf and South Atlantic coasts, usually beginning the season with a crew of raw men and boys whom at the end of the season he has turned into finished fishermen…. At least half of the men that Coles has had in his crews at Morehead City during the last 20 years were trained by Captain Jack.
“In addition to being a veteran professional fisherman he possessed an excellent working knowledge of the botany and conchology of south Florida, always mentioning the different plants and shellfish by their scientific names.
“Fish he looked upon as a purely commercial proposition, but he was a keen and accurate observer, and he was able to give information of value about the life histories of the creatures of the deep.”
The crew may not have been as impressed with Roosevelt as he was with them.
After spending a little time with Roosevelt and seeing how his health had declined and his difficulties with physical labor, Capt. Charlie Willis, at least, doubted the former president’s ability to kill a manta ray.
“You are going to get us all drowned today,” Willis warned Coles, a story in The Danville Register quoted Coles several years later, on July 18, 1919.
Whatever the crew’s doubts, the troupe of fishermen boarded McCann’s flat-bottomed skiff at their camp on the morning of March 26, 1917, and went in search of giant manta rays.

Roosevelt with the two giant manta rays, Captiva Island, Fl., 1917. Photo courtesy of Walter Coles, Sr., Chatham, Va.
The intrepid bunch followed inside waters south to the inlet between Captiva Island and Sanibel Island and entered the Gulf of Mexico through what is known as Blind Pass.
Where all this was happening, by the way, was roughly 20 miles SW of downtown Fort Myers, which at that time was still a small town on the edge of a great swampy wilderness.
Beyond Blind Pass
They did not have to look long. As they emerged from Blind Pass, Roland Phillips soon spied a giant manta ray in the distance. It was ahead of them and swimming in their direction.
In his article in Scribner’s Magazine, Roosevelt described the moment:
“It was a half mile off, swimming rather slowly through the water, so near the surface that now and then its glistening black mass appeared for a moment above. The huge batlike wings flapped steadily; occasionally the point of one was thrust into the air.”
Capt. Jack put the skiff on an intercept course with the manta ray and when the boat crossed its path, Roosevelt, with a good deal of coaching from Coles and Capt. Willis, let go with his harpoon—and missed.
He soon had another chance. The crew spied a group of four or five manta rays sunning themselves nearby.
Capt. Jack brought the skiff alongside one of the “great sea brutes” (Roosevelt’s typically puffed up words), which gave no chase, being gentle, non-aggressive filter feeders that, when they’re near the surface, dine largely on tiny shrimp, krill, planktonic crabs and other zooplankton.
As the giant manta ray lolled in the shallows, perhaps two feet beneath the surface, first Roosevelt and then Coles attacked it. They drove harpoons into its spine, one with a line attached to it.
Roosevelt wrote:
“With a flurry and a great gush of dark blood the devilfish plunged below and ahead . . .. Our launch was heavy . . . yet the big fish towed us half a mile to windward before we began to haul in on him.”
When they finally had the manta ray next to the boat, the crew gave Roosevelt a long spade lance, of a kind used by whalers, and directed him to thrust it into the creature, which he did twice.
“Everything had been quiet and businesslike up to this moment,” Roosevelt later recalled, “but as the great fish was drawn alongside and securely gaffed we shouted with exultation….”
Though it was only the first day of the expedition, Roosevelt lost all interest in manta ray hunting for the remainder of the trip. He had done what he had come to Captiva Island to do and he was spent.

Russell Coles, Teddy Roosevelt and two of Coles’ crewman from Morehead City, N.C., Roland Phillips and Mart Lewis. Near Punta Gorda, Fl., 1917. Courtesy, Walter Coles, Sr., Coles Hill, Va.
Baked Pompano and Diamond Terrapin
The rest of Roosevelt’s week at Captiva Island was anticlimactic. He and Coles and the crew packed up their harpoons and lances. Instead of a week of “savage bloody fighting” (Coles’ words before the trip), they searched for bird rookeries in the mangrove swamps. They visited an Audubon Society wildlife refuge, and they lingered over dinners of baked pompano and diamondback terrapin.
At one point, they visited a teacher and her children at the Synder School, an experimental, outdoor-oriented school on the island.

Coles and Roosevelt at the Synder School on Captiva Island, 1917. Courtesy, Captiva Island Historical Society
At night they hung around their camp and told stories of their younger days. Roosevelt recounted tales of hunting bison in the Dakota Territory and pursuing lions and other big game on safaris in Africa.
According to Gus Rice’s account of the week, the fishermen told stories of battles with big-game fish and showed off their scars from tussles with sharks, stingrays and moray eels.

Left to right: Capt. Charlie Willis, Teddy Roosevelt, Russell Coles and probably A. A. “Gus” Rice, Punta Gorda, Fl., 1917. From Vernon Peeples Collection, Punta Gorda History Center
While in Florida, the gang largely avoided newspaper reporters and the clingy local politicians chomping at the bit to see Roosevelt. However, he did give a brief speech in Punta Gorda in which he denounced pacifists that did not want the U.S. to send troops to France and called them “anti-American.”
I found also photographs at the Punta Gorda History Center that show that the townspeople feted him and his mates either on their arrival in or departure from Punta Gorda.

Left to right in the car: A.A. “Gus” Rice (probably), Capt. Charlie Willis, unidentified driver, Russell Coles and Teddy Roosevelt, Punta Gorda, Fl., 1917. From the Vernon Peeples Collection, Punta Gorda History Center
Dreaming of Cape Lookout
Coles and Roosevelt remained friends for the remainder of Roosevelt’s life. They kept up a correspondence, and the following winter Coles visited Roosevelt and his family again at Sagamore Hill.

Russell Coles’ natural history writings still sit on the shelves at the Sagamore Hill National Historic Site, Teddy Roosevelt’s home on Long Island, N.Y. Photo by Byron Smith for The New York Times
Coles brought toys for Teddy’s grandchildren, and in his diary entry of March 18, 1918, he said that he was “being treated like family.”
Around that time, in an article that reads as if Roosevelt dictated it, the New York Sun referred to Coles as Roosevelt’s “closest friend.”
Roosevelt’s health had declined further by then, and he was often weak and ailing during Coles’ stay.
Yet they still dreamed of new adventures.
At Coles Hill, Vera and I could scarcely believe it when we found a series of letters describing their plans to go shark hunting at Cape Lookout, N.C., where Coles had done most of his big-game fishing over the last two decades.
While at Sagamore Hill, Coles wrote his sister-in-law Eliza at Coles Hill, informing her of his and Roosevelt’s scheme to go shark hunting at Cape Lookout. However, he acknowledged that Roosevelt needed to recover more of his strength before they could try it.
A month later, on April 16, 1918, Coles wrote Eliza again, reporting that he had told Roosevelt that they should wait until the end of June for their trip to Cape Lookout.
Roosevelt’s poor health had pushed him ever farther to the margins of American politics, a very hard thing for him to stomach. Coles knew this and hoped to use the shark hunting trip as a public relations event that would help return Roosevelt to the limelight and restore his political fortunes.
In his letter to Eliza, Coles confided:
“The big dangerous sharks which take fine pictures are more plentiful [in late June] and would be more certain of getting a lot of grand sport . . . as I know how to fix it so that the sport will look powerful dangerous.”
In an April 16, 1918 letter to his sister-in-law, Coles discussed another part of his plans to make Roosevelt look good at Cape Lookout.
“I have got several other stunts worked out in my mind for his entertainment and one of them is a powerful secret. You remember in Roosevelt’s story in Scribner’s Magazine he tells of my writing him when he was president to improve the equipment of the Cape Lookout Life Saving Station and he did it.
“Now suppose, when he is down there with me, we should get into an awful, dangerous shipwreck and just before he died, the life savers should dash up in their unsinkable boat (provided for the station by Roosevelt when he was president) and save all of our lives and my yacht, uninjured.
“Just think what a grand magazine story Roosevelt could publish about it. Now I have got a hunch . . . that is exactly what is going to happen . . .. I can even look into the future and see just how it is going to happen, including all of the awful details.”
He concludes the letter by telling Eliza, “But keep this quiet and don’t let it get outside of Coles Hill.”
At Trinity College
Coles saw Roosevelt at least one more time, but it was not in Morehead City. Instead, they attended the graduation ceremony at Trinity College in Hartford, Connecticut, on June 17, 1918, where they were both awarded honorary degrees.

Teddy Roosevelt and Russell Coles, Trinity College, Hartford, Conn., June 1918. Courtesy, Walter Coles, Sr. Coles Hill, Va.
Roosevelt had suggested to the college’s president that Coles receive the honorary degree at the same that he was scheduled to receive an honorary degree and deliver the school’s commencement address.
Coles may also have visited Roosevelt at Sagamore Hill on that trip, but I don’t know for sure.
A Secret Revealed
The last letter between Coles and Roosevelt that Vera and I found at Coles Hill was dated August 3, 1918. By that time, they had pushed their rendezvous at Cape Lookout further into the future because of Roosevelt’s health.
In this letter Coles had other things on his mind. In the letter, Coles told his friend that he wanted to “speak of something of a more private nature.”
Evidently Roosevelt had more than once encouraged the 53-year-old, lifelong bachelor to find a woman he liked and get married.
Roosevelt’s advice must have weighed heavily on Coles. In the August 3 letter, he informed Teddy that he had kept a secret from him over that summer. He had fallen in love with a 19-year-old woman whom he had met at Cape Lookout.

Russell Coles’ houseboat, Cape Lookout, 1921. . From right to left, Mrs. Ambler, who I believe is one of Russell Coles’ Virginia cousins; Elisa, Florence and Marcy (no last names) and a pair of young daughters of coastguardsmen. Photo courtesy, Walter Coles, Sr., Chatham, Va.
From Coles’ diary and letters, Vera and I know that the young woman’s name was Millie O’ Daniel. She was from Greensboro, N.C., and she had come to Cape Lookout to teach at the little school that served mainly the children of the men at the lighthouse and coast guard station.
“She appears very nice and refined, 19 years old: had no idea what a rough place she was coming to,” Coles wrote Eliza on June 14, 1918.
In his letter to Roosevelt, he described O’Daniel as “beautiful, well educated, refined and accomplished.”
He told Roosevelt, however, that the relationship had suddenly ended.

Cape Lookout, ca. 1920-21. Photo courtesy, Walter Coles, Sr., Chatham, Va.
“There never has been a girl whose kisses equaled hers, but the break up has come and it is absolute and final,” he wrote on August 3, 1918.
I cannot think why Coles bothered to write Roosevelt about his relationship with O’Daniel (particularly after the breakup) unless he thought that he needed to reassure his friend of his interest in women.
The Dances at Cape Lookout
Coles, by the way, was not sincere with Roosevelt about Millie O’Daniel. According to his letters, O’Daniel was one of a string of young women that Coles seduced at Cape Lookout but knew from the beginning that he would abandon them at the end of the summer.
The most memorable was a woman named Harriette Davis in the summer of 1916.
That summer Coles often invited groups of young women to dine on his houseboat. On one occasion, mentioned in his diary on July 9, 1916, he:
“fed them with lemonade, peaches, pineapples, cucumbers, tomatoes, pickles (my make), a big clam chowder and then genuine finest Turkish coffee made as the Turks and Syrians make it with spirit lamp & coffee pot…. Although I never let it interfere with my fish work, etc., quite often I have these little select dinner parties on board and go in swimming with the girls.”
He may have met Harriette Davis at one of those dinner parties or he may have met her at one of the almost nightly dances that were being held at Cape Lookout that summer. They were held either at the schoolhouse or at a little general store on the Bight.
On July 15, 1916, Coles wrote Eliza:
“I am having such a good time that I don’t have to fish. Fact is, I am having … the biggest kind of a time…. There is here a little hotel run for the government employees of the great 7 million dollar breakwater being built here. The man and his wife who run it are nice people, but the principle thing about their large and interesting family is their oldest daughter Harriette….”
Harriette, he told Eliza, had just finished two years of school “in the North.” He called her his “102-pound girl” and declared that, “if there ever was a pretty, attractive and graceful little girl she is it.”

Mrs. Ambler again, this time seated on a whalebone on the beach at Cape Lookout, 1921. Photo, courtesy of Walter Coles, Sr., Chatham, Va.
He had started the summer by persuading her to break off her engagement with another man.
Coles confided to Eliza:
“She was engaged to one of the government men when I got here, but, first week I got here, she looked so awful good to one that I gave her such a rush and shot so much bull at her that I busted up that engagement….”
It gets worse.
Coles goes on to say that Harriette’s little sister had been ill for some time. As he often did for the villagers at Cape Lookout, he had been acting as her doctor.
As forthcoming as ever with his sister-in-law, he told Eliza that he has been caring for the girl with special attentiveness in order to impress Harriette. He also informed her that he had been medicating the child only a little bit at a time, rather than giving her the full dose of the medicine that he believed would heal her more quickly.
That way he got to spend more time by the girl’s bedside, and more time with Harriette. (I wondered if he was joking with Eliza, but the letter doesn’t sound that way.)
“As it is now, Harriette and I nurse the sick child all day except for an hour dinner party on my yacht and big dance at night,” he told Eliza.
And then he told Eliza:
“Of course I know that this will end like all of my other love affairs, but it surely is a most delicious sensation to love and be loved, even if I do feel a little mean in making my plans for my usual side stepping at the end of the trip.”
Evidently he and Eliza both knew that no matter how infatuated he was at Cape Lookout, or what happened there, he would always do his “usual side stepping” and flee the young woman at the end of the summer.
In a series of letters to Eliza and in several entries in his diary between July 15 and August 5, Coles described spending a great deal of time with Harriette because an unusual number of storms that summer had prevented him from fishing as much as he usually did.
He and Harriette went swimming together, they attended dances and a church revival together and he took her shopping in Morehead City.
“And now about the thing, next to fighting sharks, devil-fish, and water spouts, that interests me most: I mean Harriette,” he wrote Eliza on July 16, 1916.

Theresa Ambler and one of the island’s wild ponies, ca. 1921. Photo courtesy, Walter Coles, Sr., Coles Hill, Va.
Three weeks later, he stuck to his plan and broke up with her. He soon left Cape Lookout and returned to Danville. From that point, Vera and I found no more references to “the 102 lb girl” in his letters or diaries.
Coles remained a bachelor all his life.
“The Old Lion is Dead”
Teddy Roosevelt died in the first days of 1919. He passed away in his sleep early on the morning of January 6, in his bedroom at Sagamore Hill. His son telegraphed his siblings, “The Old Lion is dead.”
Only days before his death, Roosevelt wrote Coles in Danville. Vera and I did not find the letter at Coles Hill, but a journalist named John Leary, Jr. discussed the letter in a book of interviews with Roosevelt that he published in 1920.

Teddy Roosevelt and Coles in Florida, 1917. Photo courtesy, Walter Coles, Sr., Chatham, Va.
Death was at his doorstep, but Roosevelt had not yet seen him. In the letter, Roosevelt affirmed his interest in the shark hunting expedition to Cape Lookout and agreed that he and his son “Captain Archie” would join Coles in Morehead City on the 1st of March 1919.
Roosevelt thanked Coles for including his son and assured him that Archie was nearly his old self again.
Archibald Roosevelt had been wounded in France in 1917, while serving with the U.S. First Infantry Division.
Coles probably received news of Roosevelt’s death within a day or two of receiving that letter.
Several of the New York newspapers commented on Coles at Roosevelt’s funeral in Oyster Bay.
Wrote the New York Sun: “There was one huge man at the funeral of ex-President Roosevelt who looked not unlike Mr. Taft, although his face is much more weather-beaten, whose frame shook with irrepressible sobs. This man was Russell J. Coles, of Danville, Va., the mighty hunter of devilfish.”
Instead of going shark hunting with Roosevelt on March 1st, 1919, as had been their plan, Coles was the featured speaker that day at a “Theodore Roosevelt Memorial Meeting” at The Explorers Club in New York City. He showed lantern slides of their manta ray hunting trip to Florida.
For the rest of his life, Coles stayed in touch with Roosevelt’s family, sending Virginia hams at Christmas and sea shells to Teddy’s grandchildren.
The Roosevelt family also asked Coles to serve on the Roosevelt Memorial Association, a group of 21 men that was organized after Roosevelt’s death to build monuments and do other things to commemorate his life.

Detail of a photograph showing six of the Roosevelt Memorial Association’s members at a meeting in New York City. Left to right: Robert J. Wynne, Roosevelt’s postmaster general; Harold L. Ickes, later FDR’s secretary of labor; Luke E. Wright, Roosevelt’s governor-general of the Philippines and secretary of war; Russell Coles; Kansas senator Frank B. Kellogg; and Brig. Gen. Leonard Wood, Roosevelt’s commanding officer in the Rough Riders. New York Tribune, Apr. 6, 1919.
Most of the group’s members were U.S. senators, governors and former cabinet officers, but Coles was not alone in having been Roosevelt’s comrade in arms in the wild.
The group also included William Sewell, one of Roosevelt’s hunting guides in Maine, and T. Gilbert Pearson, an ornithologist who was a founder of the National Audubon Society.
Roosevelt never made it to Cape Lookout. I go to the Cape often though, and when I am there now I can’t help but imagine the two old men out there in the waves beyond the lighthouse, a gale blowing, drenched in salt spray, having the time of their lives, until time and the sea swallow them up.
-To be continued-
Another great story. Thanks.
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