For me that has to be the Remington 11-87. The balance sucked and it ate more O-rings than it did shells. I bought a well used 870 and never looked back.

None really, I dont buy stuff like a Jennings pistol,

Glock 26.

It didn't fit me as well as most other Glocks, since the rear "hump" is more pronounced. And it wasn't really any easier to conceal than the G19.

I tried to like it, but just couldn't come around to it after trying for a few years.

I eventually traded it for a P365, which I've now used and loved for years. It's not only a much better gun for me, it's also significantly smaller than a G26 while having the same capacity.

Ruger Single Six

Bought an older with both cylinders. Gun shot fine and my son liked it with the .22 mag cylinder.

I couldn't shoot it worth shit.

Angle and grip shape - I just could not adjust to it.

It's also the reason I haven't explored any other revolver(s) (wouldn't mind having on is .44 spl/mag to accompany my Marlin 1894)

Back in the 80"s I bought a SPAS 12 shotgun.It was a neat gun with the ability to use pump and semi auto, and the folding metal stock with the attachment that allowed you to brace the gun with your elbow for one arm shooting. But it was front heavy and just not fun to shoot.Sold it for 4x what I paid for it 20 years later.

An Interarms Walther PPK/S .380.

Jamomatic with all ammo except ball.
17# DA trigger pull.
Sharp recoil.
Hard to rack slide.

Two positive features:
Looks good.
The only LCI that I’ve ever liked.

I still have it – a safe queen.
My SIG P238 is SO much better.

My SP101 is a beautiful gun.

And I can't hit the broad side of a barn with it.

My DTA MDR

Absolute garbage rifle from an absolute garbage company.

High Standard Derringer in .22 Mag

An "I always wanted one of those" buy. Had ZERO use for it at the time, so even if it was perfect it would have been a disappointment. But it was very late productions, barrels were drilled horribly out of line, POI between the two barrels was feet apart. Couldn't keep the rounds on a man sized targets at 15 feet. (to make matters worse, I traded a beautifully slicked up, NP3'd S&W Model 10 and some cash for it. Dumb.)

I'd say two (bear with me) SIG 1911 Revolution Carrys c. 2007. The first one went exactly one shot (the one in the chamber) before choking, broke an extractor and shed parts of the firing pin safety to be mixed with the brass on the range floor. After the latter (third strike) SIG gave me a new one. Then that one's thumb safety malfunctioned. After it was repaired I sold it. A thousand-dollar POS. There are some others, but that was the most disappointing.

Sig Mosquito.

Disappointing by comparison, but my Keltec P11 was a good first pistol, it's heavy DAO trigger and sharp trigger sting [resolved with an aluminum trigger] aside.

A surplus P-64 Polish.

The good... outside it looked very close to a Walther PPK S, nicely blued, chambered in 9x18 Makarov, and was cheap (under $100).

The bad.... it was pretty crudely machined and didn't look close to a PPK S on the inside, had a 19# DA trigger, and kicked like a mule.

Khar PM9. Got rid of it as soon as I could. One of only two firearms I have ever sold.

I too had a Hi-Standard .22M Derringer. Useless for all practical use. Second runner up: Walther TPH. Would have been a very cool little gun. If it would fire twice in row!

Mine was a Marlin Model 60. It sprayed like a shotgun.

Other ones I didn’t like and sold off were the Glock 26 and CZ 75. Tried to like the Glock but couldn’t. Didn’t like the trigger on the CZ or the slide design. Too small for my big mitts.

Walther P22. The slide broke in two after a couple thousand rounds. Also a Glock 27. The thing continuously jammed. I sold it at a loss with full disclosure that it was a jamm-o-matic.

Tony.

CZ RAMI. Great concept horrible execution, I think only gun I've sold

ruger 308 AR, JAm O matic ...

Marlin camp 9