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I don't think its so much of a cartridge failing its just some get replaced by a similar caliber but higher performing with more available components. The examples Andy gave (.257 Roberts and .250-3000 Savage) were great performers in their 'day' but when you hear .25 caliber today most immediately think 25-06.
On the 'flip side' I think some cartridges are developed and show promise but without enough interest to warrant higher production of the guns and ammo, cost and availability of both (but probably more the ammo) , keep people from wanting to move into the caliber. Speaking purely as a reloader I would be reluctant to get into a caliber where I did not feel a increasing supply of components would be available and would be forced to not only search for them but have to buy new. ALSO the availability of guns in a 'new' caliber will most likely be limited and possibly not in a style or manufacturer I would want. A couple examples are evidence of this are the .327 Magnum and .375 Winchester.
 
"Failed" means commercially, as most obscure cartridges filled a need, if only within a small niche. There are many, and this recent mania with inventing new rifle cartridges is going to produce a lot of orphans in 5-10 years.

Not exactly failed, but relegated to cult status: The .220 Swift is still loaded and sold in rifles. One of my faves. Its bad rep was mostly undeserved.
The .308 Norma Magnum - essentially copied by Winchester as their .300 win mag.
Zero-to-hero #1: For decades, the 7.62X54R was a true orphan, the last US rounds being discontinued by Remington in 1950. The Soviet meltdown changed all that, and now ammo is everywhere, but the danged rifles are too expensive to collect! Worse than that, I missed my chance at an SVT40.
The .32 Winchester Special, supposedly a .30-30 turned up to 11, but in reality was indistinguishable.
Zero-to-hero #2, the formerly moribund .38 super, which was revived by IPSC and USPSA with help from Bar-Sto.
The .41 Action Express, duplicating the .41 Mag police load, killed off by a slow intro and S&W's introduction of the .40. Just got a BHP .41 conversion and am loading ammo.
The .357 Sig, .400 Cor-Bon. There are many good-to-excellent cartridges out there, but like the Betamax vs. VHS, one had to win, the other to lose. Now, both are history!
The .45 GAP as useful as it is, is unsustainable and will fade.
Essentially all 5mm/.20 calibers. .17 is a hard enough sell. The 20/.204 is asking too much.
Virtually all 6.5mm rifle calibers, as good and as popular as they are in Europe.
Many more are out there, but this is a quick list.
 
.357 Maximum
I shoot several of those Dead rounds you speak of. I love them all; sorry to all you haters:(
7mm TCU, 30 Harrett, 357 Harrett, 40 S&W, 357 Sig Love it, 30-338 win mag, 7mm-08, 243 WSSM, 25 WSSM, 270 WSM, 357 Max, 38 Super
 
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The .308 Norma Magnum - essentially copied by Winchester as their .300 win mag.

Except the 308 Norma Mag came first. It was a 2.5 inch case shared by the 458 Win Mag, 264 Win Mag, 338 Win Mag, and 7mm Rem Mag. Its what Winchester SHOULD have done. These were the first "short magnums" made to fit a 30-06 length action. Instead, Winchester had to move the shoulder forward and lengthen the case to 2.62 inches to give it enough neck for adequate meck tension. Its actually a horrible design for the 30-06 action. No COAL latitude unless you use a true magnum length action like an M700. But, the .300 Win Mag said Winchester, so it must be good!
 
How about an almost one off. the Winchester .348 only chambered in the Model 71 Winchester lever action and now days you can find some of the Model 1885 replica single shots chambered in it.

444 Marlin when I was a kid around 1968 My dad and his buddies were all smitten with it and now NOTHING.
 
I had a friend a few years ago in school who had a .307 winchester. Only one I ever saw.

It had its place in history, and is one of my favorite cartridges, but the .300 savage has gone by the way side for most. It beget the .308 and put itself out of relevance, other than for nostalgic reasons.

I'm guessing the 22TCM will fail, though a little semi auto carbine chambered in it might be fun.
 
.22TCM is fun to turn heads. And use as a flash bulb in a pinch (sorry Millennials not gonna explain what a flash bulb is :p).
 
ha ha. yeah yeah....i wouldnt wanna get hit by one lol no matter how wimpy. ive seen what a 40 does to flesh in person. wouldnt be my first choice lol.

Honestly, I love giving the .40SW guys crap. Frankly, I shot one not long ago and did quite well with it. But I still wouldn't buy one. :p
 

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