Challenge accepted! So far I’ll limit this to just the 24 core villains (treating the Ennead as a unit) plus Bugbear, Biomancer, Greazer Clutch and Sergeant Steel; I might come back later and add the other members of the Vengeance Five. I also won’t bother including OblivAeon, since his opinion of each of them is “must be destroyed” and their opinion of him basically boils down to “thanks but I’d rather exist”.
Baron Blade & Citizen Dawn - As established, both are too “arch” to ever tolerate the other directly becoming involved in anything they’re working on, so they basically would end up splitting the planet between themselves, like Spain and Portugal did during the Renaissance.
Baron Blade & Voss - Had Voss been content to leave Mordengrad alone, the Baron might not have cared, but since the Gene-Bound attacked there as well as everywhere else, Blade will always carry a grudge against Voss, though Voss for his own part probably doesn’t even notice Blade, at least not until after Oblivaeon.
Baron Blade & Omnitron - BB thinks of Omnitron as simply a machine, not acknowledging any sentience in it, and Omnitron thinks of BB as just another human to exterminate. Their relationship is not what you would call improved after the Baron builds Omni-Blade; technically the Omnitron lineage would have ended if not for that, but O5 and thereafter don’t have any capacity for gratitude on the topic.
Baron Blade & Chairman - I believe I’ve already written a full dissertation on the compare-contrast between these two somewhere; to summarize, they have really intriguingly different personalities, as Chairman is a perfectly sane sociopath while BB would actually be a very just and charitable person if not for his maniacal ego. The two would be capable of having a degree of mutual respect as imperialist monarchs, capable of transacting business between each other like Russia and China during the Cold War; their interests are sufficiently localized that they’d be unlikely to ever come to blows, which is good since neither one would give the other any quarter if that did happen.
Baron Blade & Matriarch - She probably thinks he’s sorta cool when she doesn’t know him very well; goths love an East European accent, and as long as he seems like a mysterious high-status figure, she might well romanticize him. That’d end fast if she got to know the real Ivan, as he’d be hugely disappointing to her teenage-crushing viewpoint. He for his part would probably not even notice her existence, and this becomes more true the harder she tried to make him pay attention; even if she caused serious harm to Mordengrad, he’d probably just send some robots to kill her instead of personally acknowledging any opponent so petty as a girl with a magic theater prop.
Baron Blade & Plague Rat - Not much to say here; despite the two both having a connection through Revocorp, they probably don’t personalize recognize each other’s existence to any significant extent. When captured by Task Force I-R (that should be their canonical name, RIP), the Rat becomes just another of the resources that Mark Benedetto has access to, and he doesn’t even directly report to the Baron, so the odds of BB more than vaguely knowing that the Rat exists are almost as small as the Rat being aware of anything outside his immediate sensory radius.
Baron Blade & Spite - No real relationship in canonical terms, although we can easily imagine a Disparation story where Pike Industries bundles Donovan up and airmails him to Mordengrad where he can go on a rampage (probably as a result of the previously alluded-to possibility of Chairman and BB going to war for some reason).
Baron Blade & Akash’Buta - He’s just another human for her to exterminate if he happens to be born during a century where she’s due to awaken. And he probably wouldn’t believe she existed unless he saw her with his own eyes, at which point he’d probably be interested in studying her and harvesting some of the power she possesses.
Baron Blade & Apostate - If Bezaliel ever tried to get the Baron to fall for one of his schemes, I can see that spiralling out of control very quickly. However, Apostate probably mostly prefers to play with the heroes, as they’re so much more entertainingly self-righteous about it; as two of the most over-the-top black-hat villains in a setting, these two really don’t leave any space for each other’s brand of theatricality to exist in the same environment at once, so they’d probably just kind of back off from each other so as not to be upstaged.
Baron Blade & Gloomweaver - These two are the respective commanders of large minion groups, so they’d be unlikely to directly interact, but the Battalion and the Cult very well might trip over each other a lot in pursuit of objects of power or kidnap-worthy innocents. If a series of such boondoggles were to spiral sufficiently out of control, the two might well end up coming to blows, and Gloomweaver would have a huge early advantage there, since Blade is a man of science and would not put much initial thought into having the Realm of Discord start messing with his dreams, trying to bring him subconsciously under Gloomweaver’s influence. Eventually, though, the Baron would probably figure out what was up, and build some sort of alpha-wave inhibitor chamber to sleep in, quickly ending the nightmare-god’s effort at corrupting him. Whether Blade did any more than that would depend on whether Gloomy was close to physically awakening; if it seemed likely, the Baron would prepare for it, and the Demon-God Incarnate would probably emerge into a killzone of energy cannons that would make short work of him. So the best odds Gloomy has of eventually beating the Baron is to avoid being noticed by him until he’s got about half of the planet under his thrall.
Baron Blade & The Ennead - Not being in Egypt most of the time, Baron Blade probably wouldn’t especially care about these self-styled “gods”; if they came to his turf, he’d handle them, but otherwise they’re somebody else’s problem. They for their part probably don’t think him any more impressive than a typical human; all his impressive technology means little to them, since they have magic, and spells don’t melt in the desert sun the way robot tanks very easily do.
Baron Blade & Iron Legacy - The cleaning staff of the Castle of Mordengrad were puzzled one day to discover a spot of blood and grease on the floor of the Baron’s private sleeping quarters. Despite not actually being the same Ivan Ramonat who killed Angry Paul’s daughter, he’s close enough that he would never have gotten a second’s warning.
Baron Blade & Kismet - These two are not operating at the same “tier” of criminality, and thus probably wouldn’t ever interact, nor think much about each other if they did.
Baron Blade & La Capitan - I can see there being a certain measure of fascination and respect between these two; Cappy doesn’t stay in one place or time for long enough that it would make much difference, but I can easily imagine some sort of whirlwind fling between the two, in which Blade was significantly the more invested of the pair (not so much “love” in any meaningful sense, so much as being excited at the prospect of possibly fathering an heir to carry his vendetta forward a generation). Once she sails away again, he’d probably be somewhat pensive for the next several months, wondering if a baby in a basket is going to show up on his doorstep the next week (or the previous one).
Baron Blade & The Dreamer - Dreamy probably saw some news footage of one of BB’s rampages in Megalopolis at some formative age, so a twisted illusion of him could well appear in one of her manifested nightmares. The Baron probably has no idea the Dreamer incident ever happened, since canonically it didn’t involve Legacy and thus it wouldn’t have come to Blade’s attention.
Baron Blade & Deadline - Neither of these likely has the slightest respect for the other, as each thinks of himself as being in the right, but is utterly myopic and self-fixated about it. They would make for a very “aliens vs. predator” sort of conflict, with no real victory possible, and a lot of collateral damage regardless of the outcome.
Baron Blade & Infinitor - Since Infinitor is just a madman who sows accidental havoc everywhere he goes, not having any real active sense of malevolence, he and the vengeful Baron have nothing whatsoever to talk about. Asking what BB thinks of Infinitor is like asking what BB thinks of a forest fire, and Infinitor probably doesn’t have enough lucidity left to even notice that BB exists, even while being directly attacked by him.
Baron Blade & Kaargra Warfang - “What? You speak to the great Baron Blade of GAMES! Begone, woman, I have no patience for your irrelevant prattle!” “Ha! You will make a spirited combatant indeed!” These two would be hilarious to watch in action, as the Baron does everything in his power to ignore and dismiss Kaargra, who insists on treating his attitude as a ringing endorsement of her efforts at roping him into her games. Physically getting him into the Arena would be tricky, but if she and a couple Bloodsworn just follow him around with cameras for a few hours, periodically trying to fight him, and he does as little as possible to try and get rid of them - which, given the way he operates, ends up being more than sufficient entertainment in spite of himself - and thus the cycle continues. Ultimately this won’t end until the Fickle Fans get bored of the Baron’s personality, and that might take a very long while.
Baron Blade & Progeny - This is pretty much the same question as Luminary vs. OblivAeon, although the Baron might be a little more confident in his ability to capture Progeny and then deploy him as a weapon against Legacy.
Baron Blade & Ambuscade - Little chance of direct contact between these two, even though it would be hilarious to see them trying to out-ego each other. As with the less inherently interesting Kismet match, they just aren’t operating at the same level.
Baron Blade & Miss Information - After her revelation, I can see these two being very tight; it’s a pity that VOTM Miss Info and Vengeance Blade don’t have much mechanical synergy, as the way that Blade protects Friction’s devices seems like a better fit for Missy in personality terms. Ivan hates Legacy specifically, while Aminia has an equal mad-on for the entire FV, but the two agendas are pretty thoroughly compatible, and I can easily see them having a close working relationship, which could stay completely professional or turn quasi-intimate with about equal ease. To speculate a bit, I would say that while Miss Info hates the Freedom Five specifically, and channels a lot of that hatred into the experience of having to pretend to willingly serve them, she also has a deeply instinctive service-submissive personality (after all, this other-universe Aminia was a perfectly loyal secretary up until the moment of her “death”). Thusly, in hating her bosses for close to ten working years, she was building up a strong desire to have a working relationship with someone she doesn’t hate, and thus when she starts hanging around the Baron, natural commander that he is, she would instinctively start taking a subservient role. She would be deeply ambivalent about this, sometimes triggering her hatred of having to toady to the FV, but then reminding herself that she isn’t with them anymore and can tolerate the Baron’s demanding ego in the name of pursuing her other goals, while at other times she is openly drawn to BB’s forcefulness and happily plays Girl Friday to him, often more than he’d want her to. Of all these relationships I’ve mentioned so far, this one narrowly loses to Kaargra as being the one I’d be most interested in actually developing with a fanfic or the like (I don’t really think I’m good enough to write this one though, while the Kaargra one is just a bunch of hijinks with no deeper emotion, and I actually could manage to finish that one if I just sat down and worked on it for long enough.)
Baron Blade & Wager Master - Oh god, the Baron would be SO annoyed with WM’s childish antics, and unlike in the KW scenario, I don’t see this one being funny at all in how it would play out; BB would just refuse to play, and Wags would end up sulking and stalking off when it’s clear that he’s not getting enabled the way he wants. The fact that Kaargra has an audience other than herself to play to really makes all the difference in the world here.
Baron Blade & Chokepoint - Honestly I don’t have a solid enough read on Chokepoint’s personality to be sure about this one; I think they’d just end up having a power struggle over which one of them owns a bunch of his devices. Eventually he’d jury-rig something made out of plastics and ceramic that she couldn’t disassemble, and she’d be driven off; I don’t think either of them would be likely to take it personally, so an entertaining vendetta seems unlikely here.
Baron Blade & Biomancer - I think any chance of a degree of mutual respect here was soured by the fact that Biomancer opted to create a Baron Blade imposter (the flavor text in the app whenever you play Blade vs. Luminary tells us exactly how a meeting with Repli-Blade would have gone down). The two might otherwise have gotten along decently, since they’re both hands-off master manipulators with enough of an ego to want to be personally involved in the outcome of their master-stroke (via a clone in Biomancer’s case, but he’d still be there in spirit, rather literally). But, t’was not to be.
Baron Blade & Bugbear - As a rather exceptional human specimen, the Baron would make a very tasty morsel for Bugbear’s eternal hunger, and if Luminary ever loses a game to Bugbear, I’d imagine it means a rather unpleasant fate of being kept captive for weeks while his Repair Nannites fight a losing battle to keep him alive, as the pseudo-vampiric Bugbear feasts gluttonously on this renewable resource and tries to avoid accidentally killing the golden goose. This scenario is troubling enough that I’d be tempted to “canonically” rule that the Baron has a “contingency measure” in effect whenever he fights alongside Bugbear in a VOTM match; maybe he bathes himself in some sort of chemical spray that will conceal his scent completely, to ensure that Bugbear never comes after him during a moment of weakness.
Baron Blade & Greazer Clutch - To the best of my knowledge, C&A have never explained why exactly it’s always 1958 on Greazer’s home planet, but Baron Blade has been active since the '40s, so let’s go with my personal theory that the original television waves that broadcast “Happy Days” during its heyday have only just reached the space sector where Mama Clutch’s no-good adolescent was first picking up the bounty-hunting trade. These programs were popular enough among the aliens of Galactic Cluster WKXR that they promptly began styling their entire culture accordingly, and it’s easy to assume that at least one episode would have been interrupted with breaking news of an attack on Megalopolis by giant robot tanks protecting a doomsday machine, and the cameras would have caught the Baron himself speechifying about his impending triumph (at which point he activates an EMP device to shut down all of Wraith’s devices, and the recording cuts out until next week’s show). Now if there’s one thing you can say about Mr. Clutch, it’s that he’s a man with style, and he approves of others of similar ilk; while the Baron isn’t exactly Mr. Fashion Sense, Greazer could appreciate his general “vibe” well enough that this might have been one of the reasons he first got around to actually visiting the Earth, despite its distinct shortage of employment opportunities for someone who’s always a few payments behind on his credit-hungry vehicle. The Baron for his point would find GC entirely laughable, but might suppress this reaction long enough to hire him to go after Legacy (who is after all one of the more likely candidates for that “high HP” designation which determines who Greazer is contracting upon in any given VOTM game).
Baron Blade & Sergeant Steel - This one is refreshingly straightforward; both men have a professional work ethic, a collection of high-tech gear, and a fondness for explosions, so I think they would get along fabulously. Few of the other villains are capable of as great of a level of professionalism towards the FILTER mercenary squad, so Sarge would likely regard ol’ Ivan as one of the better bosses he’s ever subcontracted with.
Whew, 28 down, 378 to go. I dunno if I’ll ever make it to the end of this list, but the last 6 entries are probably fairly self-explanatory, since all of the VOTM decks were designed together and pretty adequately reference each other. I’m pretty nigh guaranteed to get at least the second part of the list written in the very near future, since Citizen Dawn is one of my favorite characters in the entire Multiverse, and I’ll have great fun imagining her in a bunch of potential ships (which I can feel free to get a little more steamy with, since she’s of the gender I prefer).