So, I read these three books in tandem. They share a lot of crossover material from different perspectives, so reading and reviewing them together seemed like a good approach.
The NHL: 100 years of On-Ice Action and Boardroom Battles
Jenish, D'Arcy
2013
https://www.amazon.com/dp/B00C8S9YEK/ref=dp-kindle-redirect?_encoding=UTF8&btkr=1
At 416 pages, this is both the longest and the lightest read of the three. It is billed as a "Centennial History", and accordingly has a wide scope that tends to coast along the surface of NHL history. Which isn't to say it lacks substance -- Jenish tells the essential story of the league in terms of both business development and on-ice heroics. That's a much tougher task than it sounds, and could easily be done across multiple volumes rather than one reasonable-sized book. Jenish hits the high notes and pauses to explore detail in the pivotal moments (the Shore/Bailey incident, the Richard riot, the formation NHLPA, expansion, etc.).
His sourcing is a double-edged sword. Remarkably, Jenish secured personal interviews with a number of key figures including Gary Bettman and John Ziegler. He seems to have had access to all available minutes of the GM and BoG meetings, as well as to the Molson Fonds in the National Archives. That provides a lot of original or heretofore-unreleased material, which is a major strength of the book. On the other hand, framing the entire history of the league in terms of BoG meetings and executive interviews tends to create something of a "party line" perspective. One gets the impression that Gary Bettman wasn't going to interview for a book that took a critical stance toward the NHL's labor policy, for example.
On the whole, this is as good a total-picture summary of NHL history as I've personally seen to date. Recommended as a readable blend of on-ice lore and off-ice reality.
Lords of the Rinks: The Emergence of the National Hockey League, 1875-1936
Wong, John Chi-Kit
2020
https://www.amazon.com/dp/B00T9ZHO0Q/ref=dp-kindle-redirect?_encoding=UTF8&btkr=1
This work is an expansion of Wong's Ph.D. thesis, which tells you something about its tone and approach. It's academic, very well-researched, and footnoted. Up front, Wong makes it clear that he has written a business history of hockey, and he's not kidding; there's very little reference to on-ice events unless they pertain to business outcomes. So if you're looking for colorful stories about Eddie Shore, this ain't it.
That being said -- I would recommend this book to anyone who wants to seriously study the core foundational principles of professional hockey in North America. Wong goes into deep detail explaining the relationship between amateur and professional sports (and the important piece that's easily overlooked: commercialized amateurism). He provides clear, well documented explanations of how the NHA emerged from its predecessors, morphed into the NHL, and then went on to become the sole major league. He provides good insight into the motives and tactics of key figures like Frank Calder, Frank Patrick, Conn Smythe, etc.
Of the three, Wong's work features the greatest diversity of sources. He had extensive access to the NHL Archives and calls not just from official minutes of meetings, but also from personal and business correspondence. It is the only book of the three that didn't make me stop at any point and wonder about editorial bias.
Again, I recommend it as a serious academic work... less so as easy-reading for the beach.
Deceptions and Doublecross: How the NHL Conquered Hockey
Holzman, Morey
2013
https://www.amazon.com/dp/B00CMP7EVE/ref=dp-kindle-redirect?_encoding=UTF8&btkr=1
This book creates an interesting contrast to "Lords of the Rinks". Whereas Wong views the business of the early NHL through the lens of market forces and objective business interests, Holzman tells the story through the lens of personal alliances and rivalries. He focuses on the human elements that composed the early NHL, and does particularly a particularly deep dive into the constellation of personalities that surrounded Eddie Livingstone.
If there is one reason to read this book, it's that Holzman actually tells the tale of Livingstone himself. For someone whose name is familiar to so many hockey fans 100 years later, it's remarkable that so little has been written about him as a person, and most of what exists tends to caricature him as a vaguely disagreeable outcast. Holzman draws mainly from publicly-accessible records like newspaper archives and court transcripts (but not as much from "inside" sources) to fill in the picture of Livingstone and his allies... some of whom are now obscure to history for having ended up on the wrong end of a hockey turf war.
That being said, there is a distinct bias toward Livingstone's cause. At times the book verges on being an outright hit piece on Frank Calder, who is portrayed unambiguously as a money-hungry villain -- and ambiguously, as an unconvicted embezzler. The focus on personal motivations causes Holzman to overlook less-salacious explanations for historical events, which becomes much more clear when reading these three books in parallel.
Recommended as a complement to other sources, mainly for the portrait of Livingstone and as an "alternate interpretation" of the NHL's business history.