Two come to mind, both shotguns.

If I could only go back to my senior year in college I would have found a way, any way, to buy an absolutely pristine pre-war 12-gauge Superposed with a solid rib, long-tang, round knob (I think all the pre-war supers were RNLT) and wood to die for. The shop wanted $500 for it, which was about $500 more than I had at the time. I briefly thought about selling my spleen to fund it but couldn't figure out a way to do the surgery myself without risking that whole death thing. It sold a few days later and I cried for days. I've never seen one as nice as that one for anywhere near the money, although I did almost pawn my soul for a way-underpriced '57 vintage pigeon-grade Super a few years later. I couldn't get nearly enough for my soul to cover the cost of the gun however, and that one sold, too.
I still don't own a super, but I'm still looking for "the one."

My second was one I'm still physically kicking myself for. I got into older Berettas, the BL's and S56-57 series guns a few years ago and ended up with a BL-4 20 and a BL-5 12. A guy in OKC had a mint, in-the-box, drool-worthy wood, top-of-the-line 20 gauge BL-6 he would sell me for $1700.
Bl-6's in 12 are very rare, Bl-6 20s are seen about as often as Joe Biden's mystery Beretta.
I had never seen one, nor have I seen one since. I just hope the SOB who did have the $1700 is enjoying it...

Passed on a NIB Browning Model 12 repro in 28-ga for $600.

Like Chad I spent two-days trying to figure a way to buy that shotgun and still pay my mortgage.

With my vices I should have gone to law school instead turning pro musician with tinnitus and challenged auditory nerves.

Not exactly the same but I do have one that got away... Ithaca Model 37 Featherweight I got for my birthday that was stolen.

I saw a beautiful M-1 Garand on a man's wall two days ago and asked him where he got it. Gun show in Wisconson for $425- in 1999. During the assault weapon ban I said? That's not an assault weapon he answered as we both laughed out loud. Offered him $500- on the spot and he said you can get them cheap! He got on the computer and the cheapest one he could find was $899- on up to $2600-. Maybe if I'd just offered him $600-...

During my regular pawnshop rounds I found a SKB 280 in 20 gauge for $325,but ... some nimrod had removed the original stock, which was straight grip, and bent the lower tang so he could mount the god-awfullest half baked maple stock with a rollover checkpiece and rose wood grip cap!

I bought on speculation and after scouring the US and Canada via the internet, and after aa couple of false starts, found a generous soul with an original Model 280 stock he'd removed and had duplicated in a nicer grade of walnut for his own gun. Spent many hours scraping off the original epoxy finish on my the new/old stock and forearm, oh so carefully bent the lower tang back to original shape, and now have a great grouse gun that's also a blast for informal skeet.

I found a Savage 94 single .410 just like the one I traded for a 12 ga. back in 1962. I thought the little .410 too wimpy for a 13 year old and shells were twice as much as a 12ga. Besides, I could buy 12 ga. shells EACH at the hardware store! Who ever had the money for a whole box? Used to pick up coke bottles off the side of the roads for the deposit to buy shells.

Anyway, I found that little 94 at the local gun show in mint condition for $150 and tried to talk the guy down to $120, but he would only go $140. You know the rest of the story, when I went back an hour later....gone. My brother found me one this summer in a pawn shop in near NIB but the stock has been refinished and looks better than any new Savage circa 1963.

There's a shootin' iron for a grandson.

I also let a like new Savage 99 in .358 Winchester slip thru my hands a few years ago. The guy complained about how hard it kicked and ammo being hard to find and expensive. I hesitated...gone. Price one of those baby's these days! I have one now in good shape (but nowhere near NIB) that I found for $240.

I've had a couple. Biggest one, had a friend who worked at Dunham's Sporting Goods - smaller chain and not much on firearms. He was a manager.

He said a guy walked in with an old box, he wanted 300.00 for the gun inside it. Said he got it from his father after he passed and was tight on money. Inside the box was a never been fired, still in the cosmoline, Browning BAR.

He said he tried calling me to see if I wanted it, but I didn't answer my phone.

I could relay numerous stories along these lines since I used to be a gun trader by hobby because I couldn't make a living at it. Once I was visiting an old friend who collected M-12's (had two new in the box when he died this past summer) plus various other Winchesters. Once on a brief visit he showed me several M-42's. One of them was a standard grade in like new condition which I offered to buy but was turned down. After sitting for a while chatting about various guns and hunting I got up to leave. Old Charlie told me to look behind the kitchen door. There stood the M-42 I had liked so well. "Take the damned thing with you he said, they are not good for anything but looking at". I told him I couldn't take it because something might happen to it or it might get scratched, or it might get stolen. He answered "I don't care, it's your gun." I still have it... unscratched.

In 1996 a buddy of mine needed some cash and sold me his Colt Anaconda 6" stainless .44 mag for $225.00! He had only fired less than 50 rounds in it. I have come across a few deals in my life but lost out on a whole lot more.

Oh my, therapy huh? There are tears in my eyes as I write this already. I truly have a poet’s soul when it comes for great guns that I've lost over the years. I'll go through chronological order just to make this easy on my aging brain.

The first was a model 94 trapper, my dad gave it to me as my first deer rifle which I loved greatly, I carried it for many years even though I couldn't hit anything with it I eventually made the normal evolution to scope mounted rifles and I traded it back to my Dad for 100 dollars and moved on to a 308. Well that little rifle made it to my little brother and sister who both used it and sold it back for the same 100 dollars to my dad. I think its more nostalgia than anything as I look at that little gun sitting in my Dads gun cabinet and even though I've tried (he's turned down 600 on it) my Dad just smiles and says he'll pass it on to the grandkids! DOH!!

The second was a model 700 in 7mm I shot one of the nicer bucks I have ever shot at 440 yards with it. (one fence row to another) the gun would shoot ANY brand of ammo into 1 inch at 100 it was a phenomenal, light, good looking rifle, my first in Stainless. I had two rifles at the time and I went with the bigger 300 Win Mag in a 700 Sendero, which would do the same but about 3-4 pounds heavier. Great shooter!

The last would be my Browning Bar in 300. That was a great shooter also, shot deer at very long range with it. I also shot 4 in one sitting with it during a cull hunt. (When I was very younger and didn't know better) My first semi auto, semi fancy gun, it left because the fore arm had been put on green and had dried with looseness that I couldn't get out which annoyed the crap out of me. I eventually traded that gun and some cash for an 83 CJ 7 which I've had a lot of fun in and still own. So out of all those I still have something to show for it.

There are others I would have liked to have had back an M-1 Carbine of my Grandmothers, Browning A-5 of my Grandfathers when he was a boy. 410 Winchester single shot, first shotgun, and some others that I truly enjoyed but none that I sit back around the campfire and reminisce about.

My therapy, one that my Wife TRUELY loves is collecting guns. I mean hard core too. I've got everything from a 17 HMR to a 50BMG and I love it. I hope to pass mine on to 'the Grandkids' someday too, they'll just need a forklift to come get em!

CPT BRAD

A very good friend with cancer pulled into my drive one day. I was outside so I walked over to his truck and said hello. He handed me his nickle Colt Python and asked me to hold onto it for him. With tears in my eyes I told him I didnt want it, but he said he would not be here long, and if he wanted it back, he knew where it was. Years later, when the auto repair business took it's first real dive back in 2003, I had to sell it to feed my family. I was down for a while, but Ron's voice echoed in my head and I could hear him say "Hell son, family comes first". I miss you sir.

German Luger engraved with SS insignias etc. that my grandfather took off an officer he took prisoner at a concentration camp in WWII. My aunt gave it to her fourth husband who she was married to for 1 and a half years. I'll never see it again.

My first bolt action. A Ruger M77 w/tang safety in .270 with a Leupold VXII 2x-7. Not fancy, but had a decent trigger for a Ruger. Took lots of deer with it. Wish I'd never sold it, but replaced it with a "new fangled" Tikka T3 in .270. Great rifle, just not the same wood vs. synthetic. The Ruger had history.
Second one was a Colt Python 6". I was going to Colorado on an elk hunt, and for some crazy reason thought I needed a .44 mag. Traded the Python for a S&W 629 Classic---which was too much gun for me. Developed tendonitis in my wrist. Sold it also, rather quickly. The Python would be worth a mint now.
Third one was a customized Colt Combat Commander in satin nickel. Money was pretty tight, and you know the rest.