What's the Dark Circle?

Who's This? A shadowy alliance.

The facts: Created by a teenage Jim Shooter in 1968, the Dark Circle is a shadowy organization that plagued the Legion of Super-Heroes from time to time (from Adventure Comics #367). It really only has 5 members, but hordes of agents cloned from those original 5. By the 5 Years Later era, the Circle has become an organized religion, which even Tellus joined. It was also a concern in the Reboot era.
How you could have heard of it: The Dark Circle appears as a terrorist organization seeking to overthrow the United Planets in the animated Legion of Super Heroes episode "In Your Dreams", but given the state of Legion comics these days, there's not much room to grow for many of their antagonists.
Example story: Adventure Comics #367 (April 1968)  "No Escape from the Circle of Death!" by Jim Shooter, Curt Swan, George Klein and Sheldon Moldoff
The Dark Circle makes its debut and already it's won. I mean, according to the trash-talkin' Brainiac 5 splash page:
This is also the story in which the Legion upgrades its HQ from upside-down rocket (sorry--Fortress Lad) to something bigger - MUCH bigger - with their branding and everything. It's also got an armory even though we never see the Legionnaires use anything but their powers, a memorial to Ferro Lad (now standard), a fleet of space cruisers, and a control room that shoots you out of a boring briefing and into the sky. It's gonna be great once it's finished. After a good 6 pages of HQ porn, Shooter finally introduces the Circle:
Their goal: To destroy the United Planets with their small alliance of five worlds. Their mission: To strike now while Earth defenses are weak. Their table: Pretty cool. With the Legion still reeling from the latest attack by the Fatal Five, and its members scattered to the four solar winds, the Circle isn't going to get a better chance. We're with Karate Kid in Tokyo when the "dark wave" hits.
Val doesn't let himself get caught so easily, using all sorts of tricks that have nothing to do with karate to fight his way out so he can call for reinforcements.
Brainy informs him that these invaders are all over the world, overwhelming Earth forces and keeping the Legion busy in Metropolis. One by one, the Legionnaires fall.
It's some of the most exciting stuff I've seen in Silver Age Legion stories, as our heroes rally, but eventually fall victim to attrition. You'd think Superboy's presence would make the Circle's defeat a foregone conclusion, but they were smart enough to sap his strength early with green Kryptonite. With the arsenal behind guards, Brainiac 5 rummages through a stash of unopened gifts sent by UFP members for something useful. He's almost caught, but Karate Kid appears out of nowhere to help, snatched from Japan by some mysterious force. He finds the Miracle Machine (first appearance of this deux ex contraption - we're really hitting the big historical beats today) and uses his 13th-level intelligence to figure out how to use it. If his first (accidental) wish was to be reunited with Karate Kid, his second is to rid the Earth of the Dark Circle.
Holy crap! Is this survivable?! As for the third wish, it's completing the Legion HQ with a side-order or repairing all the damage caused by the invasion. Who sent the machine? A Controller, so it's a bit of monkey's paw, but that doesn't concern us right now. We don't find out here how the Circle's leaders react to their failure, but needless to say, they'll try again...

Alien invasion stories are a dime a dozen in comics, especially in this era, so Shooter's genius move here was to give them a cool name and distinctive uniform. Instead of aliens of the week, they become supervillains that can be used again and again. Though there's no attempt to create a mystery here, the concept will eventually inspire stories where the identities of these shadow figures and the planets they represent are of interest. I feel like a lot more could have been done with them over the years, including tying them into the Great Darkness stuff, from the name alone.

Who's Next? A cloned champion.

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