Video by Jessica Leibowitz

Just after 12 a.m. on a chilly autumn night in 1969, 13-year-old Robert Blake’s father shook him awake.

“Do you want to go for a ride?”

Blake quickly got dressed. They drove from their house in Eastchester to the train station, then took the subway down to the Staten Island Ferry. Blake had been on the ferry before, but that was his only experience out on the water.

From Staten Island, Blake and his father rode a launch boat to a giant tanker anchored in the New York Harbor, near Bay Ridge.

In the pitch-black night, father and son climbed a ladder up the side of the 18,000 ton ship.

“I was a little nervous,” Blake remembered. “It was beyond my comfort level.”

He was tall for 13, but lanky. The burly crewmen dwarfed him. The captain offered the pair black coffee and Blake accepted, to feel like one of the grown-ups. The ship was transporting molasses and the air had a thick sweet smell, overpowering enough that when Blake steps on a molasses ship today, he is immediately taken back to that moment: the bitter black coffee, and the warm, sickly smell of sugar.

“That was not a good night,” Blake said. “But when my father walked up on the bridge of the ship, it was like he was king. He’s in charge. Ever since then, this is what I wanted to do. I wanted to be a pilot.”

Blake’s father, Robert Sr., was a pilot for 47 years. Next month, Blake will celebrate his 37th year as a Sandy Hook harbor pilot.

New York Harbor is not only one of the largest and busiest natural ports in the world, but also the most complex. State law requires any foreign ship, or American ship with foreign cargo, to be escorted into the harbor with one of their pilots.

The entrance to the harbor from the Atlantic is protected by two thin pieces of land that jut out into the water: Sandy Hook from New Jersey and Rockaway from Long Island. These narrow outreaches have shallow shores that make entering the bay tricky.

Henry Hudson ran into the Sandy Hook Bar, a barrier of sand built up on the seafloor by downstream currents, when he tried to come into the harbor in 1609. It took him three days to successfully get in and explore his namesake river. Hudson enlisted the help of men who held long, straight poles off the sides of ships to test the water’s depth. The men who were experts with these pijls, as they were called in the Dutch shipping days, were called pijl loads, a title that eventually became “pilot.”

The New York colony was established in 1664 and the port became a bustling entry point. In 1694, after a storm prevented ships from accessing the harbor, the colony passed a bill appointing the first pilots “who shall continuously attend at some convenient place near the Hook with a boat to give all aid and assistance to all vessels bound for this Port which they are oblig’d to pilot,” the law said. The pilots were local seamen, unaccredited except for their expertise of the port and its waterways. After independence, the first New York state-licensed Sandy Hook pilot was named in 1794.

In the early decades of the 19th century, pilotage was given not based on merit, but as a political favor. A pilot job became a handout for those in the good graces of politicians.

In 1836, two immigrant ships tried to enter the harbor during a storm and sent out distress signals. No pilots were there to meet them. They stayed all night, waiting for help. Eventually, over 200 people drowned, many of them women and children. There was a public outrage and in 1837, the Board of Commissioners of Pilots was created to pick pilots worthy of the job and its responsibilities.

At the same time, New Jersey set up its own pilotage system and the two groups began to compete for the incoming ships. In 1845, another unofficial group of pilots formed, eager to get the fee from the ships that needed to come to port.

Each day, it was a race: For every ship coming in, a dozen pilot boats would rush to meet it, with at least four pilots aboard each boat. Sometimes two pilots would board an incoming vessel at the same time, but from opposite sides. Pilots went further out to sea to beat the competition, some as far as Sable Island, Nova Scotia, to ensure they got the fare.

In March of 1888, a huge blizzard destroyed nine pilot boats because they were out at sea, chasing ships. After the death of the pilots in the storm, they sold off their individual boats and pooled their resources to buy one pilot ship.

The United New York and New Jersey Sandy Hook Pilots is the same group that exists today, operating under the same shared system. Pilots split the profits from the ships they lead in and work on a rotation.

It might have lost the romance of the untamed seas, but piloting was getting harder as the ports got busier during the 20th century. Leading ships in and out without a collision was a skill and the public began to recognize it.

In a New York Times article from 1925, a reporter went out with a pilot for a day’s work while engulfed by a thick, dense fog. The pilots steering the ships communicated with each other using sound signals of bells, whistles and sirens. Sometimes, the ships themselves emitted short and long blasts of their horns at different intervals. But how could they distinguish where the sounds were coming from in the fog? Two vessels crashing into each other could result in loss of life, loss of cargo, and spillage into the water. Ships often had to pass each other with just inches between them.

“A good pilot develops a musical ear after some years’ service. He can calculate to within a few feet just how close he is to another boat by the intensity, quality and tone of the various signals,” the Times wrote. “You’ve got to be a mind reader, a musician, and a mariner, all rolled into one, to make good at this pilot job.”

During World War II, the influx of ships vastly increased. At the time, there were just 100 Sandy Hook pilots in rotation and they had no time to train new ones.

Robert Blake Sr. was an apprentice during World War II. They were so swamped, the apprentices didn’t have time to change out of their wet clothes between shifts. One freezing winter day, when his father tried to get out of his bunk from a nap, he found himself frozen to the bulkhead. Blake’s uncle was a full pilot during the war, and had to rent an apartment in lower Manhattan, which he shared with other pilots. He didn’t have time to go home, even though he lived in the Bronx.

The New York Times reported in 1945 that on their busiest day, they moved 242 ships. In a stretch of five days, they brought 386 ships to port and took out 281 others. In total, during the war, they moved 80,000 ships without losing a single one. (In 2016, the pilots average about 15 giant ships—14,000 TEUs—per day.)

Back when Blake Jr. was a teenager, there was “the list.” Each working pilot got to place one name on “the list,” and it was usually a son or nephew. The boys on the list didn’t know when or if they would be accepted into the grueling apprenticeship program that lasts five to seven years. Blake’s name was on the list when he was 14.

In addition to his father, Blake’s brother, his uncle, his uncle’s father, and his uncle’s grandfather were all pilots, extending his lineage in the profession back to the mid-1800s.

Blake went to college and got a job teaching social studies. Right after his teaching career began, the pilots offered him an apprenticeship. Two days after school let out, he went to the docks.

A 1968 New Yorker article about pilots noted that an apprentice gave up his youth to meet the demands of his job. “He has little time for movies or dance; he sees little of his friends and shares few of their experiences; if he has any girlfriends, they are probably girls he has known for a long time; and his contemporaries are likely to earn two or three times as much a week as he does.”

Today, the apprentices apply and are chosen by the pilots and the Board of Commissioners of Pilots. They shadow pilots on every aspect of the job. Then, they sit through days of exams that test their knowledge of the topography of the seafloor, location of buoys, and the depth of the channels.

The harbor isn’t a static place—buoys can change location, tides and weather can change the depth of the bay. If something is altered a day before the exam, a pilot is expected to know it.

The job has advanced beyond paper charts and a pilot’s intuition. Pilots have computers now that guide the ships and keep the cargo and passengers safe.

But the apprenticeship and day-to-day tasks breed a person with a special kind of knowledge of our harbor. A pilot named George Seeth, who started in 1906 and worked for 50 years, summed it up well in an interview for the 1968 New Yorker feature.

“A pilot doesn’t think: How many miles is it to the next buoy and how long will it take the ship with the tide halfway to flood to get there? You just know it. It’s like having a built-in computer. I’ve done things I couldn’t have figured out how to do if I were sitting down thinking about it. You get a certain instinct that tells you a whole lot that instruments never show; a change of a degree or so tells you if you’re getting tide on one bow or the other. A lot of people think a pilot is just a lot of local knowledge walking around, but if that were true, radar, sonar and good charts would be near to putting us out of business. You couldn’t do without knowing the area, but it’s skill handling ships that is your meal ticket.”

On September 11, 2001, a pilot boat was one of the first to go to lower Manhattan, right up along the Battery wall, to evacuate people to Brooklyn, Staten Island and New Jersey. The Coast Guard made the distress call, “calling all boats,” from the pilot boat.

Blake was at home in Westchester that day, but on September 12, he was on the water, moving supplies and food to the fire fighters working the pile, and giving the search dogs a quiet place to rest and wash the dust from their fur. “I got a call that they needed pilots,” Blake said. “So I went down.”

In 2009, Blake was leading a large container vessel past Staten Island when the engines failed. The ship veered toward the coast, and Blake had to stop it from crashing into the land.

Tugboats arrived to help pull the 960-foot vessel, and the ship narrowly missed going ashore. Blake said if you had been standing on the edge of Staten Island watching, it would be like seeing a mountain rapidly approaching. When he got home that night, he shakily wrote that day’s report, knowing how close he had come to disaster.

“There are standards that we hold to. But a standard day in and day out operation, it’s a dangerous job,” he said. “People fall off ladders. People get crushed by the launch.”

Blake has two sons and when they were little, he brought them onto a ship, just like his father did. Neither of them showed an interest, and he didn’t press it. Since there’s no longer a “list,” most apprentices now come from the Maritime Academy or have to go to military or naval high schools.

“I think they both would have made really good pilots,” he said. “I would like the lineage to continue. But it is what it is. They’ve got their own lives. I’ve known pilots who did it for their fathers who were miserable. They did not like being pilots.”

Blake’s niece, who is 16, might be interested. The first New York female harbor pilot was hired in 1998, and there are now four women working the harbor.

“When I was growing up there were no female pilots,” Blake said. “But now we have four female pilots and they’re wonderful. Our first woman pilot was only two decades ago, and it wasn’t first in the county. I’m sorry for that. New York should have had the first.”

Blake says that if his niece makes the commitment, it will be for life.

“No one ever leaves the job early,” Blake said. “They say, ‘I’ve done this for 10 years, I’m going to be something else.’ They don’t. You’re part of the club. Nobody leaves.”

He added, “It’s stressful. But it’s romantic. There’s a heritage to it. Most pilots appreciate that heritage. It’s what we do. It’s what I am. It’s not just my job. I identify as being a pilot. That’s who I am.”