Despite (or perhaps because of) my distaste for labelling Jews, I was recently involved in an online debate as to whether Chabad is "ultra-Orthodox" (where I argued that it is not). This led to some self-reflection and research.
Humankind have been been involved in the process of taxonomy since the dawn of time. Hashem brought all the animal kingdom before Adam Harishon and he identified them by their "names", thus grouping and categorizing them. It is a natural instinct for people to categorize things, as a mental short-cut. If I see something that looks like a lion, my mind associates it with the definition and attributes I already have established for a lion, and thus I can quickly decide to stay away. We do it for animals, vegetables and minerals, we do it for all sorts of things, and we do it for people as well.
Labelling people, however, is a double-edged sword. If a non-Jewish woman meets an "ultra-Orthodox" man, she will make this same association in her mind based on her understanding of that classification. As a result, she may know that it would be culturally inappropriate to offer to shake hands, which is a good thing. However, she may also make some cultural assumptions that are incorrect about this particular individual, and that may not be a good thing. She would do that because the process of categorization has led her to generalize and say "all ultra-Orthodox men are ...". Generalizations like that can be anything from plain wrong to prejudicial.
Western societies have a principle that "all people are created equal", yet our natural tendency to categorize often leads to prejudice and bias. The answer is to develop a deeper understanding of our taxonomies so we know which attributes are safe to assume apply, and which do not. The more one knows about a particular group, the more one is able to distinguish group behaviour from individual behaviour.
Now, back to the "ultra-Orthodox". Wikipedia defines it as the "most conservative" branch of Orthodox Judaism, and explains the use of the term "Haredi", which is preferred by people within the group (to avoid the prejudices associated with being "ultra"-anything). It does recognize that within this group, there is vast diversity of beliefs and defines subgroups as Chassidim, Litvish, and Sefardim. Another site has a similar definition - "the most theologically conservative" form of Judaism - but has a finer subgrouping, which distinguishes between different chassidic groups - Chabad, Satmar, and "everyone else", but ignores the Litvish world.
This illustrates the weakness of broad labels and generalisations. So if we say Chabad is one of many groups that fall in the (small-c) conservative end of a spectrum of Jewish theology, the question then becomes how to break up that spectrum into chunks, and delineate one portion of the spectrum from another.
If we consider how the media labels Chabad as "ultra-Orthodox", in the first of two top stories I found that do this, one was about a deal for Chabad men to enlist in the IDF where we defy the label by being the only group within ultra-Orthodoxy to take an active part in the IDF. Indeed, well before the current talk of changing the rules for mandatory army service, Chabad chassidim have enlisted in far greater proportions than all other "ultra-Orthodox subgroups". In another story on a social network that segregates men and women, again we defy the label by being the only group within "ultra-Orthodoxy" that has embraced the internet as an outreach tool, rather than shunned it like everyone else. If characteristics of the "ultra-Orthodox" include disengagement from the state of Israel and from the internet, we are 0 for 2.
It's interesting to have a look at what chabad.org has to say on this very question. Not surprisingly, they reject "ultra-" pejorative like everyone else. No-one likes to be labelled, and no-one likes to be bundled with other groups who might look similar to an outsider, but in fact are very different. The funny thing is that other subgroups would probably object to be classified together with Chabad as well. It's only the outsiders who continue to persist with these labels.
So if we rephrase and ask "Is Chabad Haredi?" would the answer change? I'm still not sure. There isn't an objective scoring system that would be able to conclude, on balance, whether a particular subgroup fit enough of the criteria to be called "Haredi". As an outreach movement, there are certainly many people who aren't (yet) practicing Orthodox but still consider themselves affiliated with Chabad. Does that change the status of the movement itself? or are these people's observances not taken into account because they are considered to be "on the road" to increased practice?
I'm caught between a rock and a hard place. I can either side-step the question and attack it as prejudicial, or reach either conclusion based on different criteria. Perhaps that itself shows how weak the question is to start with? I can only conclude by saying that Chabad is sufficiently distinct from other Haredi groups to be in a class of its own (for better or worse).