Asajj Ventress, SoD Maul and Savage Opress vs Mid CW Anakin, Late CW Kenobi and Late CW Ahsoka

Standard rules 

Savage solos

Mid CW Anakin should beat Asajj, as should Late CW Obi-Wan. Either also individually beat Maul or Savage. Ahsoka is the real weak link here. She dies to any one of the three, though I can see her putting up a good fight against Asajj. Overall, Team 2 should take it, but Ahsoka will definitely die in the process. Likely throwing Anakin into a rage-fueled frenzy where he wrecks the remaining opponents.

Ahsoka is a big weak link and SOD Maul is arguably the MVP, team 1 wins

Underachiever599 wrote:Mid CW Anakin should beat Asajj, as should Late CW Obi-Wan. Either also individually beat Maul or Savage. Ahsoka is the real weak link here. She dies to any one of the three, though I can see her putting up a good fight against Asajj. Overall, Team 2 should take it, but Ahsoka will definitely die in the process. Likely throwing Anakin into a rage-fueled frenzy where he wrecks the remaining opponents.

This.

Wait by late CW are you referring to the S7 versions of the characters? If so then I can't comment as I haven't seen any of S7 yet so I'm unaware of potential new feats

Season 5 or Season 7 Ahsoka? I'll be assuming Season 5.

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Maul ~ Kenobi
Ventress < Anakin
Savage > Ahsoka

While 2/3 of the duels would be very contentious, I don't think Ahsoka would last very long against Savage (at least not as long as Adi Gallia did). I suppose it's possible for Anakin to voluntarily swap opponents with Ahsoka whenever he senses Ahsoka is in trouble, which would probably give them a better chance at victory, with Ahsoka being able to hold out longer against Ventress than against Savage. Either way, Ahsoka is a weak link and the Jedi team would likely have to seal a victory without her (which is honestly possible). Kenobi has already demonstrated an ability to punch far above his weight against both brothers while suffering under the guilt and newfound resolve of Gallia's death, so it may be possible for any Ahsoka death to give him a similar boost. Likewise, any rage-fueled Anakin would be devastating against the Sith team.

If you discount those emotional dynamics (why, lol?) the Sith team should win by ganging up on whoever is left. Savage kills Ahsoka, then helps either Ventress or Maul kill whoever they're facing, and so on. Pretty straight-forward. But due to the team dynamics of the Jedi, I'd say they have the best chance of victory.