Charming, talented, scheming, clever, manipulative, all traits of a magnificent bastard.
Magnificent Bastard - TV Tropes
You can include heroes too.

• Starscream definitely fits this, even if he frequently fails. He's tricked the Autobots, Decepticons, and even some of the more smarter Transformers. He's smart enough to lead an army (even if his ego takes over...), used his rank as second-in-command to his advantage, and is a charming, yet sinister person.
• Shockwave in multiple continuities is a brilliant individual. He adapted to the Dinobot's combat Spotlight: Shockwave. He took charge of the Decepticons many times, and did a better job than Starscream and Megatron. He's an effective fighter and a scientist. And helped create many of the Transformers concepts in some continuities. For example in G1 he created the space bridge, in the Aligned continuity he created the Dinobots, Combiners, Insecticons and the Combaticons, in Dreamwave he created Triple Changers, etc.

 

I've seen people refer to Beast Wars Megatron and IDW Overlord as such.

 

Definitely these two.

I think swindle counts and in some situations idw whirl nearly counts but he is a little too damaged, silly and unhinged to fully count.

 

I'll second Shockwave.

 

TFA Megatron when he was manipulating people like Sumdac and the Constructicons.

 

You know, every day on the internet brings me one step closer to putting a fucking thermite grenade in the TVTROPES' server...

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Okay, ANY thread that gives us opportunity to make a Patton reference is okay in my book.

 

I'd consider some of the characters in the IDW comics as this, specifically Getaway, Megatron, Prowl and Starscream.

 

Animated Megatron.

He gains the Allspark into him and becomes very powerful, but still takes the opportunity to download Spacebridge schematics for later use. He plays Omega Supreme like a fiddle and uses him as his own tool. He uses Starscream, Omega Supreme, the protoforms, a crashed Decepticon starship, a captured intelligence agent to come up with his own terrible weapon, then counts on Starscreams treachery to finalize it, then gets rid of said traitor now that his use is at an end.

 

Definitely IDW1 Prowl. He was the greatest unscrupulous manipulator... for the greater good.

 

I'll toss in a third vote for Animated Megatron. He could effortlessly manipulate anyone he came across; Autobots, Humans, even his own Decepticons when it suited him. At the same time, his sheer charisma attracted the loyalty of pretty much everyone who followed him (save the obviously treacherous and ambitious Starscream), and he keeps layers upon layers of plans and backup plans.

 

Doubledealer. He's playing both sides against one another for personal gain.

 

IDW Sixshot and Shockwave. I would have loved to see Sixshot and Overlord throw down.

 

Getaway from MTMTE could have been that if Roberts didn't pull a 180 when he reappeared in Lost Light and just flat-out ruin him as a character.

You know what would have possibly redeemed the stupid Autobot Megatron story for me? If he was just flat-out lying the entire time while he was with Rodimus and them. It would've been glorious, a big ole slap to the faces of everyone who thought he was a changed man after literally hundreds of years being a tyrant. For how utterly easy it was to ultimately gain their (And the readers') trust and basically betray their own friends for his sake.

How laughable it is that the government decided to spare his life after all he's done. He could have given us something incredible, but it's painfully clear he cared more about feelings rather than giving us a better story.

 

Jaegertron in all of his manly might.

 

Ohhh, seeing him reunited with the DJD and Deathsaurus and then they just slaughter the Lost Light crew would have been a sight to behold. Imagine the spin he could've thrown on the survivors, if there had been any! And we could've seen Thunderclash at his best.

 

That’s basically G1 Smokescreen’s tech spec bio.

I mean, ruining every character he wrote is kind of his brand, right?

 

I think you've mistaken him for John Barber.

G1 Kickback could be described as a magnificent bastard.

Beast Wars Megatron has to be the winner. He even took control of Cybertron.

Of course some misguided individuals could see Hot Rod this way. First he gets his leader killed. His team inspire a rebellion on Quintesson overthrowing the ruling class.

After stealing a ship, he lands on Junk and charms the natives before inspiring the Autobots and Junkions, assuming command from Ultra Magnus.

Like any good attacker, he goes straight for Unicron's eye causing Unicron his first injury in his attack on Cybertron. He then conveniently separates himself from the other Autobots to find the Matrix.

He gets in close to Galvatron, lulling him into a false sense of security. He then taps the Matrix getting himself a Prime upgrade, overpowering the confused Galvatron and wickedly throws him through Unicron's side, injuring both of them before unleashing the destructive energies of the Matrix inside of Unicron.

He then impresses the Autobots with his new Primal upgrade into letting him be their full time leader before spitefully breaking out of Unicron's other eye.

Finally he takes control of Cybertron taking advantage of the Decepticons' forces decimated by Unicron's attack.

One can only imagine what he'll have done to Springer for trying to woo Arcee and I'm sorry but Springer's had it coming.

Of course, as I said, only a misguided mind could view Hot Rod's actions this way...but then he was friends with Doubledealer...

 

No, that was definitely Roberts' calling card - dramatic character rewrites to support his story.

 

He made Hot Rod, Whirl and Swerve funny. He portrayed Chromedome and Rewind as a loving, gay couple who weren't over the top or clichely camp.

He did a great job portraying Cyclonus, Skids and Ultra Magnus.

Barber undid Nick Roche's fresh approach to Prowl and Thundercracker's heroic reboot by just constantly making Prowl a prick and reducing Thundercracker to a bad joke, writing bad screenplays and giving him a bloody dog.

He focused on the usual boring suspects like Wheeljack, Arcee, Kup, Bumblebee and Sideswipe, returning the Transformers to Earth and gave the humans more focus. I didn't mind Faireborne but he brought back the arrogant Spike and made G.B. Blackrock a charmless imitation of Iron Man.