Doc Myers guessed the large crown and the HCE chips were probably from the 1950's. I'm disappointed that none of the three landed in James' new book... . (But James might have missed 'em on the chipboard, and I don't know if I emailed him when we found them. I don't think any of them had been seen before.)

Doc also said that if they had the bugle girl instead of hot stamps, we'd be looking at a slew of Z chips! (he guess-timated *S for the LCrown and *O for the HCE's)
The purple chip on the right is small crown, and it's in James' book as a 1st issue