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Some time ago, back in perhaps 2004, I was contacted by a few people via the NewRuins contact form, who were working on Robert DiNiro’s production of the movie “The Good Shepherd” which was ultimately to include an all-star cast of Matt Damon, Angelina Jolie, Alex Baldwin, and Robert De Niro among others. This film was a “based upon the true story” of the birth of the Central Intelligence Agency, known commonly as the CIA.

The first contact was from a researcher who told me that an important series of scenes took place on Deer Island, apparently due to a Skull and Bones association. Ultimately, we had several discussions about how people would get to Deer Island and how interactions might have taken place there. I was also contacted by a location scout who was interested in finding a suitable location for the scenes on Deer Island to be filmed. They needed a dining room capable of handling over 50 people in a manner that might have been appropriate to the private-club environment of Deer Island.

The "Outlook" and boathouse on Deer Island

The “Outlook” building and boathouse on Deer Island

Deer Island Boathouse Ruins

Deer Island Boathouse Ruins

I conveyed what insight I had at the time and was rather excited to have been contacted; though unfortunately a meeting with Mr. De Niro never materialized (nor was it suggested). In 2006 when the film was released, I watched with great interest to see how things were handled though I was never told exactly how or why it was felt that the dinner and interactions with the Matt Damn character would actually have taken place on Deer Island, to which I remain doubtful.

With the recent release of “The Martian” I happened to be looking at a list of movies starring Matt Damon. Seeing “The Good Shepherd” in the list triggered this memory and an interest in writing a short post on the matter … call it an ever so brief moment of fame in a negligible film career.

Of course the film is not a documentary but is historical fiction, loosely based on real people and events. Just how fictional might the involvement with Deer Island be? To a large extent that depends upon what involvement Skull & Bones had in either the original OSS and/or the early CIA.

It is definitely true that “Bonesmen” appear prominently in many aspects of American policy making (most recently, George W. Bush and John Kerry) but the suggestion that there was a large recruitment for counter-intelligence from Skull & Bones is likely overplaying the hand.

Yet it is true that Richard Bissel went to Yale but reportedly declined Skull & Bones membership, though his brother William was a member. Other key CIA players were apparently not members such a Allen Dulles (Princeton) and William Donovan (Columbia).

There are some important clues regarding how Deer Island was used by Skull & Bones members back in 1908 based upon a pamphlet that described the island and its facilities to members. Only one of the buildings — “The Ledges”, which still exists today — was made available “for men bringing their wives and family or friends.” If that protocol continued into the years depicted by the movie it is hard to imagine the large dinner party which would have taken place in “The Stone House” with all of the women present, let alone the character played by Angelina Joile who essentially corralled the Matt Damon character. Obviously they had need for plot development that was not conducive to the environment of a rather stuffy mens club.

Dinner Party Scene

Large Dinner Party Scene

The need for a dining area large enough to handle 50 people might certainly have been handled by the structure called “The Stone House”. In the old photo from the 1908 pamphlet there appears to be a large room, open to the elements with perhaps solid shutters for inclement weather. This is a very interesting building but rather rustic for the formal dining in the Deer Island dinner party scene. It was my understanding that they found a location in the Adarondaks to serve as Deer Island.

The two main buildings — The Outlook and The Stone House along with a smaller boathouse — formed the heart of the Deer Island facilities and all of these structures burned down. I have not yet determined the exact date of the fire or whether one fire took out all of those structures. A River Guide with years of experience told me there was a large fire in 1946 but that has not yet been confirmed. Since the CIA was officially formed in 1946, the Deer Island scene would have taken place before that time. While it remains a far reach for many reasons it would technically have been possible.

Deer Island as Represented in The Good Shepherd

Property Representing Deer Island

What they did get right in the movie was that everyone needed to arrive there by boat — it is an island after all — and they did include a quick scene with the main character arriving at night in a boat.

As the 1908 Deer Island pamphlet indicates, “the club launch will meet visitor at Alexandria Bay.” This was perhaps one detail I was able to provide that appears to have been incorporated into the screenplay for the film.


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