I know some will probably not like this idea, but Talia would be a good villain for him. Shiva wouldn't be a bad enemy either. He has strong ties to assassins and the like. 
 
This would bring him into similar circles as Tim and Cass, of course, but I don't necessarily think that's a bad thing.

Baddies I'd like to see Jason tangle with: 
The Wrath- From Tony Bedard's "Wrath Child"; sidekick to the original. As a crime-killer, Jason's even more this guy's arch-enemy than Batman    
Scarlet- there's nothing I'd like to see more than a disfigured lunatic Jason made into a serial killer  

Anyone else you'd use Deathpool? Living?

I dont know, but meaby hey could came with there is two Jason Todd thing, Morrison Jason goes crazy and try to kill Jason Todd. 

RedHoodsDen: 
 
You know I love almost everything you bring to the table and I sincerely respect everything you say. However,  there are a few things I vehemently disagree with you on and bringing Sasha/Scarlet to September is one of them. I think your idea for Scarlet is the best thing they could do with Scarlet if they brought her back. The irony of that situation and heartbreak that would bring Jason Todd would make great stories but I don't think the character belongs in Jason Todd's world at all. She was horrible in Morrison's Batman & Robin and served no purpose other than being a rival for Robin. The idea that Jason Todd would take her in as a sidekick makes no sense considering that he strongly believes children/teenagers lives shouldn't be put in danger because of what personally happened between him and Bruce. It also doesn't make sense that she could pretty much be on par with Robin within the few days or weeks after he picked her up from the hospital. The Batman can't even do that.
 
As Lobdell stated in his interviews he wanted redemption for Jason Todd. A good life, away from the ugliness in character both physically and personality wise that we've seen for almost the past six years: The in-sensitiveness and thoughtlessness in Brothers in Blood, the arrogance in Countdown/FC, the crazy irrational acts and thoughts in Battle for the Cowl and Morrison's B&R run, the disgust of sleeping with Talia, his father's beloved in Lost Days. Jason needs to stay away from all of that, I think the Flashpoint Priest version of Jason was implying he won't be so cynical and vile as writers portrayed him in the past but that is just pure speculation on my part. All in all, I just hope you don't wish Scarlet back in September RHD. I hope others on here feel as strongly as I do on everything I have mentioned.

You know, I thought of that one too, but I'm saving it for the slim chance I get comic work. It wouldn't be that Morrison's Todd is another Todd, but there would be another Jason Todd.  Doppelgangers kick ass. And who would literally be Jason Todd's own worst enemy? Jason Todd. It could be Doctor Hurt-y.  Really dig the split helmet, btw.  Said it before and I'll say it again, biggest missed opportunity in the Bat-family during Blackest Night: Jason Todd vs. Black Lantern Sheila Haywood. Talk about the epic mind-screwing mommy could've given Jason.

RedHoodsDen:
 
I don't think they will continue to use her at all. As you pointed out, you talked to Winick over a year ago. A year ago nobody knew anything like September would come about. It's a damn shame that editorial wanted to use her again but the extent they used her was just for B&R. I don't think she'll be showing up again and I hope she doesn't even get mentioned. As for her killing people before Jason showed up, she would've been in a mental institution if Jason never found her. There is no way she would've grown up to be a serial killer equivalently as to Jason growing up to be a thug no matter what happened in his life's trajectory. I'm honestly glad you didn't actually want Sasha/Scarlet back tho because she is a poorly conceived idea.
 
The Jason/Talia sleeping together was just sick and disturbing. I'm sure many who like Winick's writing can agree with that. The thing is it's beyond our moral perceptions of whether them sleeping together is right,wrong, or an indifference to it; He distorted the characters completely, it didn't make sense for them to do that.. you can try to justify it but in all honestly don't you think you're covering for Winick's ass? I listened to CV's podcast, I know Winick said the same exact thing you told me but I don't think he was being honest and he initially wrote that as an ego thing for Jason. I think he realized it was a mistake, he got a lot of hate for it and had to come up with something to explain himself and that was it. He's not a good writer but he certainly isn't a bad one either, people make mistakes and that was one of his biggest ones. He fucked up. He done goofed. I respect your take on it and of course this is just my perception but one I conceived unbiasedly with great analyses.  
 
I strongly believe redemption is what Jason needs. DC owes him this from killing him twenty years ago to spiritually destroying who he is now. I know everything they bring about in September won't be perfect but I'm just content that it's coming.

Flamingo should be Jason's Joker. And I can see him throwing it down with Batwoman and Huntress once in a while along with the rest of the Bat family.
  
 
The only problem I have with Jason Todd having arch enemies, is that if he hates someone well enough, and they aren't from the Bat Family, he'll just kill them. 
 

    

I guess I'm still stuck on your perception of Jason, RedKnight. It sounds more like it's about the Boy Wonder than the Red Hood. I can't really tell if you're okay with the character as was at all. Murder is even a possibility in his roots as Robin, and mass murder as the Red Hood. You didn't like Scarlet and you didn't like Talia sleeping with Jason. That's fine. But do you like the Red Hood who kills criminals? And did you like the Robin who might have killed criminals? I guess I'm at a loss for what you want the redemption for.

I cant belive no one have said this one. 
Bucky Barnes, hahahaha.....

@desperado
Actually you could do it pretty well as a bit of satire and parody and still give it depth. Literally an "in your face, Todd" story of how it went for the other dead sidekick. You just don't call him Bucky. 

.

Yeah that would be cool, what about Red X from the Teen titan Cartoon, like a antivillain character. 
Red like a happy Jason that dont kills, but take things, help bad guys, sell weapons and all those thing, but he never kills. 
It would be a good change, from bad guys kill, good guys dont.

Why does no one talk about Onyx or Night Slayer? 
It could be too crazy to bring back the Crazy Quilt?

The Wrath would be an ideal antagonit, self evident as to why. A Batman idealized villain is the perfect enemy.
 
Onomatopoeia is cold. I like him a lot and he mirrors a darker variation of Jason's Red Hood costume.
 
Onomatopoeia: Black Helmet, Black Trench Coat, Guns
Red Hood: Red Helmet, Black Leather Jacket, Guns

The Wrath would be an ideal antagonit, self evident as to why. A Batman idealized villain is the perfect enemy. Onomatopoeia is cold. I like him a lot and he mirrors a darker variation of Jason's Red Hood costume.  Onomatopoeia: Black Helmet, Black Trench Coat, GunsRed Hood: Red Helmet, Black Leather Jacket, Guns

I'd go with...  
Talia & Ra's al Ghul 
Deathsroke 
Owlman (Thomas Wayne Jr. or Jason Todd-Earth-3) 
Flamingo 
and a random new villain.

I'd go with...  Talia & Ra's al Ghul Deathsroke Owlman (Thomas Wayne Jr. or Jason Todd-Earth-3) Flamingo and a random new villain.