Carried Across The Ocean
I have long suspected some type of Lubavitch connection with my father-in-law's ancestors since my father-in-law has a soft spot in his heart for Chabad and also because it is well known that Vitebsk was once a stronghold of Lubavitcher chassidim. This is noted in the "Encylopedia of Hasidism" which states, "Vitebsk was dominated by the hasidim of Lubavitch."
Examining the shel rosh, I immediately noticed that the leftmost branch of the shin on the shel rosh did not enter the middle of the bottom of the head as is typical of Ashkenaz tefillin. I sent the picture of the shel rosh to the sofer of my tefillin to inquire further and he replied, "Definitely Chabad tefillin. The shin is not regular Ari, but Admor Hazaken."
The shin on the Vitebsk tefillin
Shin according to Ashkenaz minhagThis piece of information was a bit puzzling since the tefillin from Vitebsk also had a square kesher for the shel rosh. Yalkut Bar Mitzvah noted that the Chabad minhag for the kesher of the shel rosh is that it "must appear to one who stands behind the wearer like the shape of a printed daled." Once again, I asked the sofer how he would explain a square kesher from Vitebsk. He responded, "Simple explanation - the batim macher was Chabad, and someone else tied the knots that didn't know the minhag (the square is easier to tie)."
In order to get another opinion, I asked Shneur Zalman about them and he responded,
"Before the end of World War II there were no exact uniform standards in Chabad or in other groups (for example Brisk as a minhag did not exist). In Chabad the new rebbe promulgated the minhagim publicly in 1951 as he had no seed. In Europe, there were all sort of Chabad minhagim and variations of them. Most Chabad people in Europe intermarried with Misnagdim and so things became complex . So to sum it up, it very likely that the tefillin from Vitebsk had aspects of Chabad customs to them as well as some aspects that did not conform."
When I asked my father-in-law if his father had instructed him on how to put on the tefillin, he answered that indeed he had. He told me that the hand winding that he was shown was not the winding according to the Chabad minhag, but rather a standard Chassidic winding minhag.
Standard Chassidic minhag