The first amendment has nothing to do with it. A big part of it is that type design was largely a European activity until the late nineteenth century/early twentieth century. American typefounders lived off copied designs (and even as America gave birth to Linn Boyd Benton, Bruce Rogers and Frederic Goudy, there was still a lot of stealing happening at the big American foundries (the innovation happening in the US tended to be more technical than artistic. American Monotype has approximately zero noteworthy typefaces created under its auspices, while its English counterpart had a long streak of notable designs released in the first half of the twentieth century which are responsible for the look of modern book typography).
This history of stealing designs for competitive reasons was a bit part of why there was resistance on the part of the big players in the industry to seriously pushing for typeface design protection. While Bitstream had Matthew Carter designing excellent faces for them (and overseeing licensed designs from ITC), the vast majority of their type designs (all the ones named style + number), were slavish clones of other companies' designs. The big companies make the bulk of their typeface income not from retail sales but from licensing deals (e.g., Apple and Microsoft made licensing deals with Adobe and Monotype respectively for most of their system fonts, although some smaller design houses like Hoefler & Co., Bigelow & Holmes and Tiro Typeworks (off the type of my head) have managed to get some of that licensing. The late Arthur Baker made the biggest part of his lifetime income from a licensing deal with HP.
You are correct that in the 19th and early 20th century, we used to 'pirate' just about everything. Thomas Edison made a fair amount of money doing this with movies, for example.
However, you are incorrect about this particular item. Sure, one can produce a font file that is licensed and distributed with a computer/web browser/whatever and it's pretty easy for a determined large group of users to not pay for more than a single copy of said font. At the very least, a user can take said font rasterize / embed it in a thrilling rendition of 'Mary Had a Little Lamb' along with every other letter/symbol the typeface provides entirely legally that all are free to use. More commonly, someone else can re-implement the font that is an (almost?) perfect copy of the original. That's how the computing world got all of those TrueType fonts that were knock-offs of Adobe's Type I fonts and a big part of why Postscript is not really a thing for most users anymore.
"Copyright law does not protect typeface or mere variations of typographical ornamentation or let-
tering. A typeface is a set of letters, numbers, or other characters with repeating design elements that
is intended to be used in composing text or other combinations of characters, including calligraphy.
Generally, typeface, fonts, and lettering are building blocks of expression that are used to create
works of authorship. The Office cannot register a claim to copyright in typeface or mere variations
of typographic ornamentation or lettering, regardless of whether the typeface is commonly used
or unique. There are some very limited cases where the Office may register some types of typeface,
typefont, lettering, or calligraphy. For more information, see chapter 900 , section 906.4 of the
Compendium. To register copyrightable content, you should describe the surface decoration or other
ornamentation and should explain how it is separable from the typeface characters."
Notice the 'building blocks of expression'... that's the whole First Amendment bit. IIRC, there was a Supreme Court case about this.
The first amendment has nothing to do with it. A big part of it is that type design was largely a European activity until the late nineteenth century/early twentieth century. American typefounders lived off copied designs (and even as America gave birth to Linn Boyd Benton, Bruce Rogers and Frederic Goudy, there was still a lot of stealing happening at the big American foundries (the innovation happening in the US tended to be more technical than artistic. American Monotype has approximately zero noteworthy typefaces created under its auspices, while its English counterpart had a long streak of notable designs released in the first half of the twentieth century which are responsible for the look of modern book typography).
This history of stealing designs for competitive reasons was a bit part of why there was resistance on the part of the big players in the industry to seriously pushing for typeface design protection. While Bitstream had Matthew Carter designing excellent faces for them (and overseeing licensed designs from ITC), the vast majority of their type designs (all the ones named style + number), were slavish clones of other companies' designs. The big companies make the bulk of their typeface income not from retail sales but from licensing deals (e.g., Apple and Microsoft made licensing deals with Adobe and Monotype respectively for most of their system fonts, although some smaller design houses like Hoefler & Co., Bigelow & Holmes and Tiro Typeworks (off the type of my head) have managed to get some of that licensing. The late Arthur Baker made the biggest part of his lifetime income from a licensing deal with HP.