Who are these gentlemen?

[Drew Hause]

Well done Chris!

Using a L.C. Smith, "Sparrow" had the Long Run on Targets for 1899 with 211 straight May 8 at Peoria, Ill. and used a Smith at the 1899 GAH at Live Birds.
Using the nom de plume of “Robin Hood” (as a rep for the Robin Hood Powder Co.) he used at Smith in April 1900 at the GAH at Live Birds, then broke 25 straight at the Grand American Handicap at Targets in June 1900 with his own Young Repeating Arms Co. pump.
When that effort failed, he was a demonstrator for Baker Gun & Forging (W.R. Crosby having left Baker for Hunter Arms in 1899), a trade representative for Peters, and in 1907 he was shooting a Parker.
In the 1908 GAH Preliminary Handicap, now using a Winchester 1897 he tied the winning Amateur Score, 95x100.
He won the 1926 GAH with an Ithaca SBT.

[Big D]

Drew - To refer to Destry as "Rotund" is to do him a disservice. After having lost about 70#, he might be more accurately described as resembling Slim Pickins

[Drew Hause]

The figment of his former self Destry?

[George M. Purtill Member #28]

And where were these fellows shooting?
There seems to be a grand stand in the left background and quite a house, lake and sailboat(s) in the right background?

[charlie cleveland]

never seen destrey so thin and looks like he has bought a new pipe.....looks like hes still shooting the higgins.... charlie

[Bill Murphy]

Our hero, Destry, was headed for Argentina with a squareback and a backup.

[CSL]

Drew, That is good early time-line info you provided on Young...

Given the date of this photo and the appearance of his double gun, I would say it is indeed a Smith that Charles is holding... In the 2 images below you can see Chas was certainly a snappy dresser at competition shoots, his Smith looks to have a thin recoil pad and also a leather hand protector on the barrels... You can also see the shooter sitting next to him has a higher grade straight grip Parker with the original style SSBP... I wonder if O'l Sparrow was shooting a Smith Pigeon grade during that 1899-1900 time period?...

Best, CSL
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[Drew Hause]

Chris: Dr Jim is currently doing a bit of Smith international missionary evangelism but upon his return I might be able to pursuade him to check the records to see if "Sparrow" received a Pigeon gun.
BTW: DGJ should publish Smith Pigeon Gun infro soon. We'll see if some of the interesting rib images made the final edit

[Bill Murphy]

Isn't the extra "hitch" on the back of the grip checkering a clue to its grade?