Colt SAA made in 1903, 4 1/2-inch bbl, nickel with pearl grips. In 99% condition with box and factory letter. It's worth 10X what I paid for it. I'd never find one in that condition again for a good price. Plus I have a Winchester 94 in 30 WCF and an 1897 riot gun made in the same year, so it's part of my Old West Trifecta.
Colt Detective Special I bought from Jim Cirrillo back in the 90s.
Steyr SSG-69 with double set triggers, Schmidt & Bender Scope Kahles rings. 308. Looks like Chuck Norris' rifle from opening scenes of Lone Wolf McQuade. It's my go to rifle for almost everything, except silencer testing because for all the good Steyr did, they cocked a few things up in their typical fashion. Yeah it would be expensive, but this one has sentimental value.
Israeli Uzi SMG, full auto 9mm, made in Israel as a machinegun, Pre May Dealer Sample not a converted Model A or B.
Cobalt Kinetics Adeptus. I helped Cobalt a lot in the early days. I got them on the covers of three different magazines; advised the owner on different things and helped him sell off the company. They were going to make 1911s and 2011s before they sold everything to a new owner and I got to test all the prototypes. He told me to pick one out as a gift for helping him. There was a 2011 with a big funnel and a splash of blue in the color. The serial was C0BALT. When I realized that I told him, "No, you should keep it, just send me another one." he didn't care and told me it was mine. He'd keep C0BALT1.
HK P7M8. This is what got me thinking about replacement. I was carrying it (paid $650 in 1998) and an editor for USCCA's magazine asked me to write an article on my carry gun almost 10 years ago. He said "send the guns, we'll take all the pics". I looked them up to see what they were going for(I had a P7 with the heel release, too) and said, "Nope. If they got lost I would not pay the going price for a used one." I took the pics for the article. I sold the P7 for a really good price (I had paid less than $500 for it and got $3K) but I'd never part with the other one.
Century Arms AR (C15) in an A2 configuration. I imported a few thousand of these rifles from Guatemala as parts kits in July/August of 1997 when i worked for Century as a buyer. A few went on to be props guns for Black Hawk Down. All parts except lower receiver and barrel are Colt originals and of course I upgraded the trigger. It has sentiment and I've never seen another come up for sale in 27 years.
S&W 657 3-inch Lew Horton, I have a history with this one. It got away from me once when I needed the money and I tracked it down and bought it back 10 years later.
Seecamp LWS that I got from Seecamp, himself, when I was a young poor and they were going on the secondary market for the price of a Colt Python. It's been my faithful companion for 30 years.
The first 1911 I built as a young gunsmith. The only thing original is the bare lie and frame from SAI, everything else from either Wilson Combat or MGW was added and fitted by me to replicate a USMC MEU (SOC) build.
They'll definitely be the last to go when I start selling things off in my 80s.