The common element in this series seems to be an original mascot design on the head-end of the pennant; with the city name spelled out and a player (or two) wedged between the lettering. On all but the Washington pennants, this seems to be the case. (Greg: just curious as to why you think the Washington pennants belong to this series.)
We can eliminate Keezer as the maker. Although they always used monochrome graphics, like those in this series, they also always used tassels. Thick tassels. The kind that are sewed in tight and never fall out. Moreover, on many (but not all) of their pennants from the late 1940s and 1950s, they stamped their maker's mark on the reverse. To my knowledge none of these pennants have any such mark. Also, I have a Keezer catalogue from ca. 1950 and the artwork used for the 16 big league baseball teams is different from these; and, different from those shown on Greg's ca. 1956 little league ad.
I think we can eliminate ADFLAG, too. Some pennants from this series feature tassels; but, the majority do not. To my knowledge ADFLAG never used tassels.
That leaves WGN. Their production of sports pennants began in the 1930s; but, it was limited to Chicago sports teams. Or, so I thought.... They also began using monochrome designs; but switched to polychrome about 1950. Most importantly, they used tassels in the early 1940s; but, seem to have stopped using them sometime in the mid-1940s.
To me, this last characteristic is the best evidence that WGN manufactured this series. Of the usual suspects, they're the only one that makes sense.
Of course, it's possible some other maker made these that we all haven't yet identified, like Annin. There has to be at least one other national manufacturer from the late 1940s that we haven't yet identified, and this series may be part of their work.
It's interesting this mystery maker made both an NY and SF Giants pennant for the series; but, only a Brooklyn Dodgers. I'd like to think I know LA Dodgers pennants as well as anyone and I cannot think of any Los Angeles Dodgers pennant that looks like this; or, utilizes that same bum smoking cigar artwork.
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