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Who would have the best synergy with my Stuff:

Beast-09
Black Ivan

War dog

Great Bears of Gallowswood
Iron Fang Pikemen (Leader and 9 Grunts) +UA
Man-o-war Shocktroopers (Leader and 4 Grunts)

Fenris

I've never played with Black Ivan, but I've heard his extra point cost isn't really justified unless you use him with Harkevich. Otherwise, you have a lot of tankiness with this list, give pButcher a try and consider swapping Black Ivan for a Destroyer or even a Juggernaut. I also don't see Fenris played much so you might want to consider scrapping him and adding another 'jack. You have a lot of arms to swing for his feat turn though, so that's why I recommended pButcher. Hope this helps!

You're kind of going around it in a backwards way... Usually you design the list around the caster rather than picking the caster based on the list. The problem here is that you don't have much "commonality" between the units you want to use, so its hard to maximize the benefit provided by any one caster over another.

pIrusk
pButcher

Spring to mind. Both can buff the jacks and support the infantry.

i would say drop the bears and grab 2 iron fang kovnik because they buff shield wall troops, and can be jack marshals, so you could also drop your jacks and fenris and have a beserker in each kovnik's control ant then go for irusk or butcher

or better yet scrap the 2nd kovnic and men o war, and grab wintergaurd and kovnic joe and rockiters and ua armada

then grab a devistaror and keep beast 09 and then grab E sorcha, 6 points left for fenrisand 1 point or somthing 6 points

but for the list you have grab either irusk or butcher

Keep your list right where it is. bring pbutcher, psorcha, or pirusk.