Looks like a 3 way race this year for the Woodland West between Greendale, Pewaukee and NB West. Pewaukee was real young last year so I could see them really improving. Coach Chossek has really improved NB West as well. They give us Panthers fits. That being said, i’ll go with Greendale to win the Woodland and go deep in the playoffs. Brust could be a Ridgeway in the making and Shumway has the same demeanor as Witkowski did a few years ago.  Good to talk football in May.
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I live all the way across the state, so my perceptions may not be accurate, but I still see Eisenhower at the top spot. Although they do lose a lot of seniors, they still return quite a few great players. Not being from the area/not watching them consistently, I don't know all starters returning for each team, but for all-conference selections, Eisenhower, Greendale, NB West, and Pewaukee all return at least 5 all-conference members or honorable mentions each.
Eisenhower: OL, DL / QB, RB, DB
Greendale: OL / OL, DL, DL, LB
NB West: RB, DL, DB / OL, OL, DB
Pewaukee: OL, DB / TE, OL, LB, DB
Eisenhower will miss a lot of their defense, but they do get a sizable chunk of their offense back. Greendale should be a defensive force for Woodland teams and improve quite a bit overall. NB West also becomes and all-around threat, and as you said, Pewaukee returns a lot of young yet experienced players that should allow them to compete with the top teams not just in the Woodland, but in D3 as a whole.
Overall, I think these four teams will finish in order of Eisenhower, Greendale, NB West, and Pewaukee, but the gap between them will be much tighter than last season. I like all four of these teams' chances in the post season, and I wouldn't be surprised to see these teams upset each other in the deeper playoff games if they do end up in the same section.

The East is a big question mark for me. South Milwaukee and Cudahy seem like the favorites, but Greenfield also returns a crazy nine players from all-conference selections. Messwood doesn't seem like they will be too good this season, but I could be very wrong.
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The race for the top spot in the West may be the best it's ever been. I give the slight edge to IKE (a program that has re-found its swagger) over Greendale, but both Pewaukee and NBW will have a say.

I just don't know where WISCO is as a program at this point.

WAC will likely be extremely sophomore-heavy with their small senior and junior classes. They have almost nothing returning as far as line experience. Just eek. Pius should be slightly better off than WAC. They also have a tiny senior class, but the returning juniors have lots of game-time under their belt.

In the East, I have to think that if they don't have to forfeit games again, Milwaukee Lutheran with Kenneth Payne returning in the backfield will be the favorite alongside Omarion Bartlett and Greenfield. Messwood will take a step or two back as the cupboard was a bit bare behind last year's quality seniors. Cudahy remains a wild card after sneaking into the playoffs last year and they aren't short on experience. SM and Whitnall should remain consistent to what they've been with both having a real shot at the top. BD may be in a bit of trouble as the bulk of their roster a year ago were seniors. - Follow me. Because we all need a bit of sports snark in our lives.

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The West will be an absolute bloodbath. At this point I think WISCO is just waiting to put in the East to regain some of their mojo that was lost when they came over from the WLT (Imagine that all the WLT schools outside of WBW and Cooney are faring much better than WISCO in football these days. Is this the Pre-WIAA-WISSA merger timeline again?)

The East will be a muddled affair early on but I think after a few weeks Greenfield and Milwaukee Lutheran will be the major players in the East.
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The farther I get from coaching or living in these communities, the less I know / have to say about these programs every year, so take this for what it's worth... but I still can't resist a good Woodland thread. 

To me, in the West you kind of know what you'll get from Ike, Greendale and Pewaukee. They're all solid programs that are unlikely to deviate more than +/- 2 wins from a 6-2 season. Credit to the coaching staff at those schools and the culture they've established. The question of who emerges from that group with the best record comes down to the players... who has the most difference makers? Who has the best / strongest group of seniors? (I have no idea.) Who stays healthy?

New Berlin West is the school that makes it interesting because they're clearly chomping at the bit to join that group. One of these years they will make that jump.

Wisconsin Lutheran… yikes. Every year that passes since Denoyer moved on sees them fall back closer to what they were before he arrived. You talk to guys who played there and you realize what a special run they had and how much work (and talent) went into it. They will have a shot when they move to the East.

Meanwhile, Pius XI reminds me of Thomas More in that they haven't been a football school since an HoF coach stepped down a generation ago. Every former Metro Conference school not named Marquette or CMH needs to send their AD down to Racine and pay Coach Miller to teach them how to build a program from nothing.

And then there's the East. Until I see otherwise I'd have to think Milwaukee Lutheran is the team to beat, but at least two of these schools will probably do just that. I simply have no idea which two schools it will be.

Greenfield has some talent coming back but they lack the consistency and commitment of the top West schools. Cudahy might have less talent, but assuming their QB comes back they probably have a higher ceiling within the division. South Milwaukee brings back a really good downfield QB/receiver combo as well as Coach Galewski, but the big difference between now and his last run at the helm is in the powerlifting program which was at its height from 2007-2010 or so. I'd expect Whitnall to improve and Messwood to fall off.  

All of these schools and all of these kids have a shot at changing the game between now and Labor Day. It just depends on what they do this summer. Good luck to them and I hope it's a fun season to watch.

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