Montauk Chapter 4 – Grandpa Herbert Circa 1918

Every time I visit my Mom she wants to give me stuff. Sometimes it’s dollar values from the Goodwill store. Sometimes it’s my stuff from my youth. Sometimes it’s family heirloom stuff. About six months ago on one of my visits she had a few books laid out for me, one of which was my Grandpa’s Naval aviator flight log. Needless to say it was one of the best batches of stuff I ever took home. I looked through the log and found plenty of interesting notes and I also found a few photos that were tucked into the book. It was cool enough in the moment but it took on an even deeper meaning as we prepared for our trip to Montauk.

See my Grandpa was a Naval aviator in WWI. He was first assigned to a base in Bayshore, NY in July of 1917. He was transferred to Key West on the day after Christmas later that year and eventually wound up in Montauk, NY on March 15, 1918 where he would remain for the duration of his service. I had no recollection of this when I was in Montauk in 1973 and even if I had I doubt if it would have had much impact. I was a nine year old boy after all and the only thing that mattered at that point was playing in the surf and hanging out with my cousins. I can only imagine how poignant it was for my Dad, his brother and my Grandparents at the time though. As I look back I am overwhelmed with emotions as the history of Montauk now takes on all new meaning.

James Henry Herbert Sr. flew 155 missions from Montauk Naval air base between March 1918 and January 1919. On some days he flew as many as five short missions and on other days he was in the air for up to four hours on one mission alone. The flights ranged in purpose from patrolling, to bombing to searching for other lost airplane to hunting for enemy submarines. I can’t even imagine the sights and experiences my Grandfather must have had as a young man flying over the coasts of Long Island. My cousin Hal told me a story over the summer about how Grandpa was flying a mission and noticed a submarine that lacked U.S. markings on the top. Instead of dropping a bomb he made a second, lower pass and determined that it was the shape and size of a U.S. submarine and might have lost its tag. He decided not to bomb it. Later while he was being interrogated for a potential court martial the Captain of what turned out to be a U.S. submarine notified his superiors that a U.S. pilot surveyed the ship and decided not to bomb it. My Grandfather went from being a goat to a hero for not sinking the sub via friendly fire. I had never heard that story before.

Clearly my favorite discovery from reviewing my Grandfather’s flight log was when I found out that he actually survived a plane crash. On July 29, 1918 my Grandpa flew a two hour and twenty five minute patrol mission. At the end of the mission his plane went into a tailspin and fell into the bay. The plane was a total loss but both my Grandfather and his partner survived. In the Aviator’s log there is an entry that says:

Flight No. 248 – Seaplane A-952, pilot Ensign J.H.Herbert, USNRF., while spiraling over Great South Bay, machine went into a tail spin and fell into Bay, resulting in total wreck. No responsibility placed on pilot; no disciplinary action taken. Signed G.B. Strickland Lieut., USN Commanding.

This moment in history is so incredibly valuable to me and to be able to see the actual document that was signed in person 94 years ago is a piece of the past that most families are not lucky enough to have access to. I am so grateful to all of those who have had the foresight to preserve the precious pieces.

As I said there were a number of photos tucked  into that old Aviator’s log. One of them was of the plane nose down in the shallow water of the South Bay. Somewhere in this murky photo my Grandpa is being taken from a plane that crashed in three feet of water on the coast on Montauk. The same depth of water I played in with my Mom, Dad and cousins in 1973. Pretty amazing in the grand scheme of things! The snapshots are reflective of 55 years between moments in time but equally significant and no question ties our family history to this little hamlet in the town of East Hampton, New York.

I didn’t get a chance to figure out exactly where my Grandfather crashed his plane 94 years ago. If I go back next year, which is likely I will do a little more leg work and try to walk on the beach where he miraculously walked away from a plane crash.

I’m so grateful for being part of a family that values history. As I wrap up this Thanksgiving weekend I thought there was no better way to finally make this long overdue post. Now onto the holidays to make new good memories and to cherish old ones…


About Jim Herbert

I've been wanting to write my whole life. By age 45 it had amounted to nothing more than a storage locker of half full journals and a lot of unfulfilled dreams. Then Paris in the fall of 2011 happened. It was the catalyst I needed to consistently blog. At first I had a hard time hitting the publish button, but now two blog sites and over 300 posts later I'm hitting my stride. I'm also a budding speech writer. I've recently been heavily involved in the Chicago Storytelling scene and have also won the Chicago Toastmasters Area 66 International Speech Contest. Check out our website at for more details about the amazing things that are happening in my life. A book or two are nearing completion. With another Paris trip on tap for Easter of 2015 I can only imagine that there are Infinite Possibilities on the horizon!!!
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