So many great choices across the decades . . . tough to make it down to just a few.
Keith Hernandez and Mike Bryan published "Pure Baseball: Pitch by Pitch for the Advanced Fan" a couple of decades ago (1994), a detailed account of Hernandez' thoughts and musings on two games (one watched in person, and one on TV). Hernandez may have been one of the smartest players in the game in the late 20th century (he would probably argue himself that he was) and his observations about the minutiae that go into each and every play are astute and often humorous (as a Cardinal fan growing up who first saw Hernandez play in 1974 in Double A at Little Rock, I was predisposed to like the book, I'm sure, but I think I'd feel the same either way). I learned a whole lot from it.
https://www.kirkusreviews.com/book-r...pure-baseball/
"Sixty Feet, Six Inches: A Hall of Fame Pitcher & a Hall of Fame Hitter Talk about How the Game is Played" takes the form of alternating comments on the same subjects by Bob Gibson and Reggie Jackson, and offers a lot of insight into the game in general and those two compelling figures in particular. Again, I'm a bit biased being a Cardinal fan when younger and being a huge fan of Bob Gibson to this day (my first major league game was in the Astrodome in 1971, seeing Gibson against the Astros). The co-author here, Lonnie Wheeler, also helped with Gibson's outstanding earlier biography, "Stranger to the Game", which I also highly recommend.
Reggie Jackson And Bob Gibson Talk Baseball : NPR I haven't gotten round yet to reading Gibson and Wheeler's most recent effort,
"Pitch by Pitch: My View of One Unforgettable Game", in which Gibson talks his way through every one of the 144 pitches he threw in Game 1 of the 1968 World Series, but I expect it's equally compelling.
Everyone knows Jim Bouton's "Ball Four"; Jim Brosnan's "The Long Season" and "Pennant Race" set the stage for all the "insider" books on sports to come, including Bouton's, and are unjustly ignored these days.
Life in the minors: Pat Jordan's
"A False Spring" is a classic, Steve Fireovid and Mark Winegardner's
"The 26th Man" should be on anyone's list. Journalist Paul Hemphill followed a promising Braves farmhand named Marty Molloy for the 1994 season at Durham and produced
"The Heart of the Game: The Education of a Minor-League Ballplayer", still a favorite. For a more recent take on life in the minors, Matt McCarthy's
"Odd Man Out: A Year on the Mound with a Minor League Misfit" paints a pretty vivid picture.
Scouting? Winegardner's
"Prophet of the Sandlots: Journeys With a Major League Scout", about the scout who signed Ferguson Jenkins and Mike Schmidt among his 50 total major leaguers, will enlighten you and break your heart. Kevin Kerrane's
"Dollar Sign on the Muscle: The World of Baseball Scouting" is a great history of scouting up to the time it was published, well before the current "Moneyball" era. And of course "Moneyball" itself, if you haven't read it, is a must.
On the fiction front, I doubt there's a more entertaining baseball novel than Mark Harris'
"The Southpaw"; people know the sequel, "Bang the Drum Slowly", but most miss the first book in Harris' series about Henry "Author" Wiggen, and that's a shame as it's a really good novel (not just a really good baseball novel) and isn't as sentimental. It describes a different world (it was published in 1954), but the voice Harris develops for his narrator is unique and vivid and keeps you intrigued throughout.
I really could go on all night and into the next day. Anything by Roger Angell is worth your time. Lawrence Ritter and Donald Honig's collections of oral histories of ballplayers from the early years of the game up through the mid-20th century are musts. If you're looking for something down a different alley than these, let me know.