Leo Underwood

Whatever his code name from Kerrigan is (or possibly even earlier from Ravager days)

30

He/Him

Kerrigan Mafia, Blackmailer/Networker/Info Broker

Human

Maximilian Befort

5 FT 10 IN

Fit

Dark Brown

Black

He oftens keeps it just a little bit longer, in order to do a more shaggy, combed over look

I'm sure

Nah

Leo has always liked to dress to impress, but not in a, business professional kind of way but a "I'm gonna look like a bad boy that you can still take home to your mom" kind of way. He has a signature leather jacket that he is basically never seen without, and it has been mended a few times over by magic and is also spelled to keep it from wear and tear.

I'm sure there's some lol

Leo has always been something of a firecracker. He is dependable, suave, confident and just as enigmatic as his best friend Sam. They were best bros, and spoke of being each others wingman when they were older, wondering if they'd always be on the run.

He is a talker and a spinner of tales. He never quite had the brains like Sam or the brawns like Isaac, so he always used his mouth and his super extroverted and big personality to get them the connections they needed.

Leo is often described as lazy, roguish, immature, tactless, and brazen. He typically tries whatever he can to shirk responsibility and work. However, he is also extremely steadfast and loyal, and has learned over time not to shirk from his duties, no matter how much he might grumble about it. He enjoys gambling and drinking, as well as pursuing women (and sometimes men), though he is careful never to pursue one who isn't open to his attentions.

He is also very much a Jean-Ralphio type, someone who is always coming up with crazy schemes to make money and doing his best to not do any actual work. His mouth is often bigger and faster than his brain and gets him in trouble, and he's not particularly trustworthy to those outside his circle. He always lives lavishly and spends his money as fast as he gets it, which is why he's always chasing the next big job or the next big break.

Bisexual

His leather jacket. While he would never say it out loud, part of the strict sentimentality behind it is because it was a gift from his mother when things were particularly bad at the house with his father. Now that Lily is long dead and gone, it's one of the few things he has left of her and so is super protective of it.

Leo is the only child of Syrus and Lily Underwood. Home life for Lily and Leo was pretty awful. Lily had gotten pregnant as a teen and had rushed into the marriage because the two of them thought that's what had to be done. Syrus was a mean and broken man and despite periods of good times, always relapsed back into his old ways. Lily and Syrus fought all the time and only stayed together "for their son", and also because Lily did not ever feel she was in a place where she could safely leave him. He was verbally and financially abusive and Lily was forced to work all the time to try and keep a roof over their heads and food on the table because of the tight rein Syrus kept on the finances.

Because of that, the two of them were particularly close to Patricia Skiles, a family friend and neighbor who lived closed enough for Leo to be able to escape to her house but far enough away to be out of Syrus's range of influence. Lily often used her friend as a free babysitter since Leo was so close in age to Patricia's adopted son, Sam. For awhile Lily and Patricia probably regretted that decision as Leo and Sam turned out to be terrible hellraisers and troublemakers when together and their powers combined were enough to get them in shit loads of trouble all the time.

After Patricia died, Leo was more than happy to help Sam with stealing from his old man. Syrus was often the target for their early schemes and stealing until it got too close and too dangerous for them to continue. Then Leo started pulling in his other connections for help, like Jake, and the two of them met Isaac.

After Sam's dad died, Jake left the picture and Leo, Sam, and Isaac formed the Ravagers and started to pull in other members and the dough, things took a turn for the worse in the Underwood household. Syrus had finally fully snapped. Thanks to the Ravagers, Leo was making enough that between him and his mom, Lily could finally get a divorce and leave the fucking asshole. That seemed to be the final nail in the coffin. He made the terrible decision to get physically abusive with his wife.

Leo came home one day to find his dad dead. A fall seemed to trigger a heart attack, or so his mom said. They never spoke about it, and Leo was not particularly sorry he was dead. Still, legal complications meant that Lily was basically left with nothing. So Leo offered to cut her in with the Ravagers. He had first envisioned her being sort of like Sandra, a mom to the group but not someone who would really be super involved in the missions... but it turned out his mom was a cutthroat bitch and a killer thief. Who knew?

No one outside of Sam knew that Lily was Leo's mother, not even Isaac. They opted to keep that under wraps in case the others in the gang found it weird since Lily had Leo so young and looked quite young herself. Lily was like a mother to the whole group, anyway, so it wasn't a big deal.

His split from the Ravagers might have been mostly mutual at the time - Sam was upset but resigned, Isaac seemed to think mostly 'good riddance' - but it was not so between Leo and his mom. Lily did not want him to go off and get into all the hard life of crime, drugs and trafficking and whatnot, but nor was she willing to leave the Ravagers to go with him. Leo was deadset. So they hardly spoke after he left besides some awkward catching up every blue moon, and when he met up with Sam to give him the contacts to the drug rings much later.

He regretted doing that pretty bitterly later, after it was all said and done. He had to hear through the grapevine that the Ravagers had been wiped out, and that his mother was dead.

Leo was taken in by the Kerrigan mafia when they did a hostile takeover of the territory and group he was in previously, and they saw his usefulness as an informant, blackmailer, and info broker. Leo was quick to swap loyalties as the option was join or die and he very much wanted to live.

He and Isaac rebuilt their relationship when Trinity was brought back into the Kerrigan fold and they are now best friends - although they do still grate on each other's nerves and they are not as close as each of them were separately to Sam. Leo also alternates between being SUPER PISSED and teasing Isaac relentlessly about his relationship with Lily, ranging between making frequent jokes about Isaac's adoptive mother (although never within Madison's hearing because he would like to keep living) and calling Isaac his "step dad".

He welcomed Faina into the fold easily enough and likes to play the "big brother" role, much to Faina's annoyance. For her part, Faina thinks Leo reminds her a lot of Mitch and often tells him this because it annoys him to be compared to him.