If I recall correctly, the reason the captaincy letter are on the wrong side is because, when the NHL introduced the new jerseys after the last lockout, they required an increase in the size of the logo on the crest of the jersey. Because of the shape of the Red Wing logo (highest point in the upper right), there wasn't enough space between the crest and the logo for the patch.

But I agree, even after all these years it still looks stupid.
- Sven22

tip of the climbs the shoulder so high that the "C" would be pratically on the shoulder, I believe the "C" on the right is the lesser of two evils.