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Oldsmobile just didn't have a clue how to attract Musclecar buyers until 1968. .... Oldsmobiles 1967 auto show display consisted mostly of hubcapped Cutlasses and Delta 88's. Their 1968 auto show display had girls in go-go boots talking about 442's.
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Well, I think through 1967, there were not many companies that knew how to attract musclecar buyers, so singling Olds out is unfair. I don't think there was a decent campaign from any manufacturer (other than Pontiac, for obvious reasons, and Chevrolet, due to sheer might); one could argue that ads like these helped Plymouth . . .
. . . but don't forget that GM could not use racing in advertising, so that created an opportunity for creative cleverness (apologies for the alliteration!) that hadn't really been seized through what I'll call the first phase of the musclecar era (through 1967; 1968 was the 1955 of musclecars).
By 1968, there was a maturation in the youths of American and the musclecar market. Don't forget that the previous summer we had the Summer of Love, which completed the severe shift from 1950s-style rosy cheekiness to 1960s hairy anti-establishment confrontation. Look at any manufacturer's advertising between 1967 and 1968 and you'll find they all matured and tried to talk the language of the kids. Some of it looks corny to my eyes, but I was born too late and that's my parents' fault!
It's acknowledged that the 4-4-2 was the greatest threat to the GTO in the early years, but Pontiac's marketing was so far ahead of everyone else's then that I don't think Olds should be singled out. And the new-for-1968 400 sealed Olds' fate as an also-ran because the equity they had earned with the earlier performance cars was lost . . . and wouldn't really be recovered till 1970.