The barber pole look may be historical but many fans of the modern team aren't in love with it.
Wait, many fans aren't in love with it? Everything I have heard (from both friends who still work with the team, as well as friends who work for independent retailers) claims the exact opposite: it is our most popular jersey as far as sales are concerned, AINEC.
And even aside from sales, just on this very website (which, I don't think is in question, is mostly populated by the "under-30" demographic),
the "Tournament of Logos" polls I ran in the offseason had the Heritage "O" as the second most popular logo of all time among users on this site.
It might help explain why there is less of a buy-in because the association is not as strong with this generation.
Less of a buy-in? Again, everything I have heard as far as sales are concerned paints completely the opposite picture.
The standalone "O" adds a bit to the negativity. Boston has a B but it's in a crest. On their Heritage jersey they spell the name Boston. The "O" inside a crest would have looked better imo and it didn't have to be a centurion.
Look, you are well in your rights to dislike the jersey. No one will argue with you about your own personal preference. If this is the way you interpret the jersey, that's totally fine. If you see the "O" as negative, that's your opinion.
... Just understand that you are in the minority.