The venerable Journal of Information, Law & Technology (JILT) is reborn as the European Journal of Law and Technology. Volume 1, Number 1, available free online, is a special issue, "A History of Legal Informatics":
- Let there Be Lite: A Brief History of Legal Information Retrieval (Jon Bing)
- The Global Development of Free Access To Legal Information (Graham Greenleaf)
- How Structural Features of the U.S. Judicial System Have Affected the Take-Up of Digital Technology by Courts (Peter W Martin)
- Legal Informatics – A Personal Appraisal of Context and Progress (Richard Susskind)
- Jurimetrics Please! (Richard De Mulder)
- The Rise and Fall of the Legal Expert System (Philip Leith)
- From Legal Thesaurus to E-Signatures (Fernando Galindo)
- Socrates and Confucius: A Long History of Information Technology In Legal Education (Abdul Paliwala)
As you might imagine, Canada's LexUM, CanLII, and Quicklaw are mentioned but are not, in my view, given enough emphasis in the historical essays.
The essay by Susskind (he was a general editor of the predecessor JILT) is in effect the first chapter of his book The End of Lawyers?, and is well worth reading even if "legal informatics" is not of special interest to you.