Smart Mailboxes aren't smart

I have set up a smart mailbox to pick up emails to and from a colleague. I have entered his name (from and to contains). Only 4 emails have been placed in the smart mailbox. How can I get the system to pick up the rest?
(OS X 10.9.1)
Many thanks,

How funny. I stopped by looking for an answer to fix the problem I'm having with sync, random signatures, and Conflict Resolver, and then saw this thread and remembered I've got this same problem as well. I just figured it was because my computers can't/aren't running the same version of Mail. My G5 uses 2.1, while my MacBook Pro uses 2.1.1. The way I have Mail set up on my G5 has taken several years to get just right, with many smart boxes, rules, etc., and truthfully, it's just too much of a pain to deal with Mail on the MacBook Pro without all of my personalizations in place, so until sync really syncs everything between the two machines, I don't even turn on Mail on the MacBook Pro. I would like to be able to, so I'm hoping someone has a fix for this.
Dual 2.7 G5 & MacBook Pro 2.33 Duo 2   Mac OS X (10.4.9)  

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