When acccompanied by a 牌 character (similar to but not identical to the one on the left) I think it would just clarify that the prize/award is in the form of a medal (as opposed to money, a diploma, certificate or whatever).
I did a Google search using '"Japan" "flying eagle" medal' and found some similar items. They apparently are some sort of award from local newspapers but I have not determined exactly what they are for.We really need someone fluent in Japanese. It’s not written in hiragana (the simplified phonetic Japanese lettering system) but in kanji, where each character represents a whole word… and there are thousands of them.
The only one I recognise is the one on the right which is 賞 and means “prize” or “award”. When acccompanied by a 牌 character (similar to but not identical to the one on the left) I think it would just clarify that the prize/award is in the form of a medal (as opposed to money, a diploma, certificate or whatever).
I don’t recognise the monogram below the eagle but, since it uses western alphabet, it’s unlikely to be war-related. I would think post-war and it might be sports-related, some kind of civic recognition or for an industry achievement. Without a full translation it will take some tracking down since it may well be something very specific of a local nature rather than a ‘national’ award. The translation might be more difficult if the inscription includes something like a company name.
You found the answer another way... I was going to post the second part to my message on the newspaper topic but got busy with University papers. The last three characters on the back of the Item appear to say 新报社 xin bao she which means newspaper. The 新 meaning news as in the chinese 新闻。 The "kanji" (as Red-Coat mentioned) on the back of the item appears to be Chinese Seal script... 篆書 the pinyin is zhuànshū. A classical style of writing Chinese characters.