Why is Red Hood important to Black Mask?

This is a question I've been pondering since I read RHATO #1 VOL.2. I'm usually bad at guessing comic twists. At least lately. Still let's look at the facts and guess from there.


SPOILERS AND SPECULATION AHEAD

If you read Batman Under the Hood you're familiar with these two playing off each other. Winick wrote Roman Sionis as a crime boss who constantly got out smarted by the much younger Red Hood. But that's not their relationship in Red Hood and the Outlaws Volume 2. This Black Mask is smarter and more dangerous to the point Jason has to take more risks just to figure out what's going on.

It starts with Batman asking Jason to figure out the connection between City Hall and a new international crime cartel. While doing this he learns the mayor had been injected with a techno-organic virus that he cures while making the city believe he shot the mayor. Someone at the super villain bar Jason visits claims they could put their own candidate up for mayor now but that probably isn't related. This is when one of BM's men approaches him. Was BM responsible for the mayor being co-opted? It seems likely. I'm not sure if BM suspects he's being played with or is toying with Jason.

I did wonder if he knew Jason's ID when rereading the issue. The link with Ma Gunn being biggest factor since he tries to blow her up a week after Jason was given his card, which feels like he's trying to spur him into action. The timeline between BM meeting Gunn and the explosion isn't clear. Gunn says she got out of jail a month ago and was supposed to get her license the previous week. Which happens to be the same time Jason cured the mayor. The four henchmen claimed they wanted to kill her at the restaurant yet we never get a reason why they didn't. You would think the only thing that would stop them would be their boss. Why didn't they stay around to make sure she died in the explosion?

Did someone stay and see Jason unmasked?

I'm probably reading too much into those details but speculation is fun.

The whole thing really smells fishy when Jason attacks the limo BM is in and how BM reacts. He claps and says Jason is everything he was hoping he'd be. Jason seems somewhat puzzled that he'd be expected.

At one point I wondered if Roman was even the guy under the mask as his old look is on Jason's screen. It would make sense if he wasn't as Jason notes that Black Mask used to be a low level black marketeer who's now better at hiding his operations. Not to mention he's operating on a much grander scale. Ma Gunn does refer to BM as a young man (*1) which is odd as Black Mask does say he doesn't have any children to take over his business implying he's older. (*2) This theory isn't strong especially since Gunn is familiar with Roman. Sure anyone can wear a mask but could they really fool someone that's known Roman since he was in diapers?

Lobdell also refers to Black Mask as Roman in one of his recent interviews. But I figured I should at least mention this theory to compare when issue three comes around. It's supposed to gives us a better idea why BM wants to work with Jason. Maybe his connection to Batman?

Black Mask talks to Jason in a way that tries to appeal to him then offers him a spot as his second in command. Yet he doesn't give any details to what he's doing at this point. Next comes the test to see what Jason is willing to do. BM kills his men himself when he's denied. The strange part is that he doesn't make a big deal out of it. He claims it shows character and it does, it shows him who he's working with.

...But remember how he acted when Ma Gunn declined his offer? Black Mask wasn't amused or forgiving. He said that he owned her and this is a woman he knew for a long time. Where else he's far more accommodating with Jason not doing what he wants. Now with the information we have it doesn't look like BM can own him as he currently has nothing to hang over Jason's head. He doesn't trust him enough to tell him anything despite being the supposed second in command. If you don't trust someone why send them on a mission to get a "game changer"? 

Though Black Mask also claimed the train had nobody on it. Could this be a set up for Jason to keep Artemis busy while the henchmen make away with the goods? Possibly. 

The arc is called Fathers and Sons but so far we haven't seen too many references to those bonds. Obviously Bruce and Jason though the title is plural. Roman and his father? Mentioned by Gunn then Jason bringing up their status as orphans. The only other mention is Black Mask when he offered to make Jason his heir. How sincere Roman is will be up for debate for awhile since there's not much to go on.

*1 This is questionable given her age as she could see most as "young."

*2 Another exchange that could go either way since Black Mask could just be saying that to make a better speech.