There are a lot of questions surrounding the Schipperke breed, and a lot of misinformation out there. Here we will attempt to give you the best researched answers that we have to these questions, all citing original historical material, not secondary (most cites are from the Chasse et Peche magazines, an early Belgium publication).
Does the name Schipperke mean "little captain" or "little shepherd"?
Answer: In truth, neither. It means, "little boatman". The word Schipperke was first chosen for the breed in 1880 by the Compte de Beauffort, when he invited them to be shown in the Belgium Cinquantenaire by offering prizes. In most of Belgium, they were known as "spitz" or "Flemish Spitz", and in the Brussels area they were occasionally called "skupperke". Most of the original founding breeders referred to them as boat dogs, and defended the name as such rigorously (one admitted that they were on the canal boats but felt they were the guildsmen's dogs more than boat dogs). During the 1880's, the Belgian Shepherd dog did not exist as a breed, it was created and developed by Prof Ruel, one of the leading Belgian vets during the time, with the aid of Louis Vander Snickt, one of the founding Schipperke breeders. The idea that the two breeds might be connected was first suggested in 1894, in response to a German author, who implied in a letter that the Schipperke was nothing more than a variety of the German Spitz (it was very important to these first breeders that the Schipperke be a 100% Belgian dog, only). Even then, the Belgians wrote that they could have been called scheperke (little shepherd), if they were not already called a Schipperke (little boatman). Indeed, the article even mentioned that there were Schipperkes still in that day to be found on the canal boats and barges. The idea the name could mean anything else was only popularized years later, and often the arguments made in favor of this are found to be flawed against the breed's primary history.
Why is the Schipperke docked?
One of the misconceptions that can be disproved by reading the original history is that Schipperkes were prolific in early Belgium. Indeed, in 1880 they were considered to be an extinct breed. They had been popular years ago, and examples of the original type were diligently sought. Throughout the 1880's, the breed was being "resurrected". During this time period, the idea that the entire breed was originally born tailless was widely promoted, though many Belgian breeders expressed their doubts at various points. As they were seeking to bring a breed back from extinction, the focus was not on finding tailless examples, but the best examples. As they stated at the time, "The tail comes last". This said, the intent was to bring the breed back, then breed back and promote naturally tailless examples until they bred true for that trait. So.... why didn't that happen? Because they did not understand the genetics at play... the bob tail gene is dominant and a dog which carries two of these genes will either die before birth or shortly after. Moreover, the bob tails tail lengths vary from appearing tailless to appearing to be full tailed. This means you can never breed true for the trait. It is quite likely that the "legends of old" of them being born tailless arose from the fact that some of them were, and these were the ones that were commented on and remembered. To this day, there are bob tails born in the breed and some are born appearing to be tailless (we have a few of these).
There are numerous Schipperkes throughout the history of the breed known to be bob tails. The first bitch sent to Great Britain (Flo) was a bob tail, as well as the later CH Wizard, as well as CH Velart's Felix and his sire, CH Walrose Ebony Captain ROM, in America. Bob tails were regularly discussed and advertised in early Belgium as well.
In 1891, Prof Ruel, who was very familiar with the breed, wrote a rather scathing article, which was widely published, that called out the Schipperke breeders on this idea of being naturally tailless. After this, docking legends became more and more popular. In it, he mentions the bob tail puppies, some of which were very short, but he concludes, "We are of opinion that the schipperke is not (a tailless race), and is not at all characterized by the congenital absence of the coccyx. The tailless schipperke is almost always an artificial, adulterated, falsified product. This dog is born like its congeners of the other races of the canine species with a perfectly developed tail; it is often very long and very thick at its base; he would carry it up on his back if he was not deprived of it in time."
Before this time, the idea that they were naturally tailless is what set the breed apart, and it was what gave it popularity. Later, they continued the tradition through docking, but not without damage - the most popular year for the Schipperke was like 1889, when they were stolen from their owners in Belgium and England for exporting and sales purposes. After that, articles were frequently published about the Schipperke being tailless for "the same reason the fox terrier is" - they are docked. Their early popularity fell, never to return to that level again.