“Writing this has employed a day”

Dr. Benjamin Church, Jr., used a variety of ways to send messages into Boston after the start of the war, including:

• crossing the siege lines himself in April 1775 and pretending to have been placed under arrest.
• having a letter “sewed in the waist of [a paid confederate’s] breeches.” That unnamed man was stopped and “confined a few days,” but the letter wasn’t found.
• possibly piggybacking on a letter from Gen. Charles Lee that Church arranged to be sent into Boston in early July.
• meeting a Crown agent in Salem. William Warden told the Loyalists Commission “he was sent by General [Thomas] Gage to Salem and Marblehead to receive intelligence from Dr. Benjamin Church, but failed to execute his business.” Church wrote in July, “I have been to Salem to reconnoitre, but I could not escape the geese of the capitol.”
• asking Gen. George Washington’s staff to send in a letter through the channel they established to communicate to their agent, John Carnes. That document was sent through the hands of military secretary Joseph Reed, Lt. Col. Loammi Baldwin, a man named Tewksbury raising sheep what’s now Winthrop, and a waterman going into Boston.
• And of course asking his mistress, Mary (Butler) Wenwood, to arrange for someone she knew in Newport, Rhode Island, to deliver a letter to a royal official there to pass into Boston. Unluckily for them, she chose her ex-husband, Godfrey Wenwood.

Of those communications, only the last letter survives and can be connected with a transmission route because it was intercepted, proving to be Church’s undoing.

For that letter through Newport, Dr. Church used a cipher for added security. One of the many fine questions asked after yesterday’s presentation on Dr. Church was if there were any other ciphered letters from him in Gen. Gage’s papers. I don’t think there are others. And in fact, since the one that incriminated Dr. Church was never delivered, there aren’t any at all.

As part of his defense Dr. Church displayed and translated a letter from his brother-in-law, John Fleeming, written using the same cipher. The doctor said Fleeming had asked him to use the cipher. That letter survives only in printed translations. Earlier Church told Washington that he had received and destroyed another ciphered letter from Fleeming, but that might have been the same one he later displayed.

In General Gage’s Informants, Allen French identified other letters from Dr. Church in the general’s papers on the basis of internal detail (the writer was about to leave for Philadelphia) or handwriting. Those were all in plain English.

As is the long letter written on 24 Sept 1775 and published in Henry Belcher’s The First American Civil War, which I identified in this post as probably Church’s last report to his royal handlers.

It appears, therefore, that Church used the cipher only in exchanges with Fleeming. Why not all the time?

One reason is that having a cipher and sending lots of coded letters might have raised questions. In one of those letters in Gage’s files Church said that an encounter with an angry man named Timothy had prompted him to destroy his cipher lest people suspect him.

Another factor may simply have been time. It took extra effort to copy each letter symbol by symbol. In the intercepted letter the doctor complained, “Writing this has employed a day.”

We might say that using every means to conceal a spy letter would be time well spent. But in Church’s case, the cipher roused Godfrey Wenwood’s suspicions and was soon broken, but the letters the doctor sent in other ways remained secret for over a century.