I'm restoring a few of the pens, but I do have pens for all of these, just not in the picture.
From left to right:
(back) red 444 "hockey puck" dip-less set, unused with the paper instructions still inside
(front) black 116 "8-ball" desk pen holder, pre-war (all metal center as opposed to the plastic insert you see in the others)
(front) maroon (red) wedge holder
(back) green Stylist Desk Set "flying saucer"
(front) 427 Dip-less double well
(back) print out of the top part of an advertisement from 1880 for Esterbrook Steel Pen Company
(front) red 116-R, was new in box with matching dark red pen which is waiting for a new sac at home.
And not pictured is my army-brown 407 Dip-less (single version of the 427) engraved with "Property of Air Force U.S. Army" with matching pen. That's over on my desk. Also, my 445 (444 hockey puck, but with a chain that connects the pen with the base) which is in use at home by my computer. The chain helps make sure that I always have a pen at hand that can't "walk away."
Re: Esterbrook desk sets and dip-less family portrait
Dual port unit looks like a rabbit ear antenna from the 1950s.
I have one of the old eight balls from the old Pensacola, FL, City Hall, 1986. They used to use it for a ballpoint at the cashier's. When the City Hall from 1905 was donated to the State for a museum, we were allowed to take some mementos. I was the IT manager at the time.
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