This is a photo of an original penned in Engrosser's Script in 1909 with a pencil portrait drawn behind the lettering. The text is a quote from William Jennings Bryan and I believe the piece was done in memory of JF Hook's brother fairly soon after his death.

Unfortunately the quality of this image is very poor (it's a scan of a photo copy of a photo of a photo stat... ). It's hard to say for sure, but I believe the original of this piece has a profile or portrait of some sort floated behind the lettering similar to the Engrosser's script version. As far as I can tell, it's undated, but I would assume it was also completed some time in 1909 or soon after.

The text is a quote from William Jennings Bryan and I believe the piece was done in memory of JF Hook's brother.

Christian Endeavor Certificate with three resolutions made in honor of Clarence E. Hook

I don't have much info on this piece, but based on the Quincy, Ill location included on the top banner I would guess it was done while he was a student at the Gem City Business College which would place it around 1904 or 05.

A photo stat of the original with added flourishing in the corners.

Signature in the bottom right, but I can't for the life of me tell whether there's a date there as well.

Based on the content and date on the letter this would have been written when he was finishing at the Gem City Business College, looking for teaching positions and before he was hired by Temple.