I suspect it would be fair to say that Columbia was good to Miles. He built up a massive library with them; and my guess is that, between up-front "salary" and residuals, such as royalties, the experience was far more rewarding for his bank book than his previous engagement with Prestige (now in a box that covers the period between 1951 and 1956, which includes the formation of the quintet with Coltrane and rhythm provided by Red Garland on piano, Paul Chambers on bass, and Philly Joe Jones on drums). On the other hand the production work for Prestige involved some of the best minds of those years, including Bob Weinstock, Ira Gitler, and, of course, Rudy Van Gelder (and the CD box was produced by Orrin Keepnews); and Columbia just never had people of that caliber in their shop. One way of putting it might be that Prestige was a family of people dedicated to bringing the best in jazz to those who could only hear it on recordings, while Columbia seemed more interested in making jazz "intellectually respectable" to those who would not be inclined to listen (rather in the way that Joseph Papp would provide a "reasonable facsimile" of "experimental theater" for those who wanted to claim experience with the experiments without getting dirty from them).
While Keepnews always seemed to be busy with one project or another in building up a CD library that could cultivate a new generation of jazz listeners, the Columbia label (whoever its owner happened to be at the time) took more than its own sweet time in rolling their Miles resources out of the vaults. To make matters worse, not only were they tardy; but also they were more than a little arbitrary. Thus, they did not take long to release The Columbia Years 1955 - 1985; but this was little more than a tease that only vaguely hinted at all the stuff still hiding in the vault. More thorough collections would eventually trickle out, many of which, like the compilation of sessions with the "second quintet" of Wayne Shorter (sax), Herbie Hancock (piano), Ron Carter (bass), and Tony Williams (drums), are absolute "musts" for learning to listen; but, even when the content was as valuable as that of this particular collection, the packaging was rarely better than dreadful. Where labels more serious about jazz would provide well-organized accounts of the recording sessions, not to mention specific notes on who took which solo and observations about what they were up to at the time, Columbia would come out with these inconvenient hard-bound "books," which could never open flat and would therefore not sit on a table while you were listening, offering poor organization of the content that mattered the most and an excess of hagiography.
Needless to say, none of this made much difference to those of us who were serious listeners. We just wanted to hear the tracks, and any of the others factors rarely mattered that much. On the other hand I have to wonder how any potential new listeners would react. Just what was the production team for these concoctions thinking when they dreamed up these packages?
This brings me to a final observation, which concerns what I hear on the radio when I want to listen to jazz, either on XM Channel 70 or the local public station, KCSM. The bottom line is that I hear a lot more Trane than I hear of Miles. Now one reason for this is that neither of these stations seems to want to have much to do with all the electric stuff that occupied Miles for about his last fifteen years. To be fair, I do not hear that much of Coltrane at his most experimental on the radio; but experimental Coltrane still has higher currency than "Electric Miles." My question, however, is whether or not I hear so much less of Miles' "second quintet" because radio stations are as annoyed with the packaging as I am. (Mind you, some of the impulse! packages are not much better!) I have no idea what the answer is, but I still cannot help but wish that the Columbia producers had shown a bit more respect to the listeners most interested in their product.