Easy peasy.

I think it was 1927. The rear of the photo in that link is dated 1927. I also found this NY Times article from 1927 about Dan Howley Day.

Awesome find. Love the graphics.

Rare Pennant Auction
 

I’ll first state that I have no skin in the game by sharing these auction links. Just wanted to pass along in case there were any Red Sox fans that wanted to score some rare penants off a smaller auction site for hopefully a good price.

It appears they are from 1915 and 1916.

https://auctions.ejsauction.com/auct...ant_F474D8393C

https://auctions.ejsauction.com/auct...ant_AD44709A72

Interested to hear what our experts say about these…

The 1915 pennant was made by a technique called "Applied Felt Lettering." Simply put: the individual letters were likely cut by a dye press; then glued to the felt using rubber cement. This was done to cut down on the sewing needed to sew each letter on.

The reverse bears witness to this method: there's no evidence of stitching; and after 100+ years, the rubber cement has bled through the felt.

The 1916 pennant is really cool. If this maker made a companion pennant for the '16 NL champion Brooklyn Dodgers/Robins, I've never seen it.

I may have the sister pennant to that Red Sox, although this is wider and the date and letters are stitched. I think I’ve seen a 1915 Red Sox that more closely resembles this but I can’t find it again ..

Picked up a very nice example of this Cubs pennant and it unexpectedly came with some cool provenance. I've seen this pennant attributed to the 1950s, but it clearly was still in circulation on May 14th, 1967 (took a little research to pinpoint the year).

Why can't all pennants come with a letter like this?

Nice! Dick wanted to get home so he wouldn’t have to put the top up on the car. LOL. :p

It's funny...A simple note, but I can visualize in detail everything in it.