I have numbers in my outlook listed under primary. About 86 contacts with #s in primary.
How come they aren't showing up in my blackberry!? Is there some setting?

There is no "Primary" number in the BB.

Well... are you syncing your Outlook to the BB? How so?

Is that "primary" field mapped to which BB field?

And finally, has this worked in the past, or never worked for you?

This has NEVER worked.
How do I do this mapping?
I was surprised at first when I was receiving calls and I didn't see the names and I thought how strange it was.
Then I realized I had the #s in Main (per my Treo : Palm Desktop) so I switched them all to primary (Outlook doesn't have Main) but now I can't seem to find Primary on my Blackberry.

How do I go about resolving this?

Like John said, there is not Primary or Main. You just need to sync your Outlook to your BB... set the Address Book to sync to your BB.

Found it! Thank you!