Not sure what happened, but I messed around with it and here's what I came up with.
For some reason the index got messed up so that anything in the current index would not show the preview. I figured this out by stopped indexing altogether for a few days and then turned it back on. Once it caught back up, all the new emails have the correct preview. So, I deleted the current index and had it reindex the entire computer and everything is fine now. I just did it Friday night so it wouldn't bog down the computer while I was working on it. I can only speculate what actually caused the issue, but deleting and reindexing should fix it if it's exactly what I experienced.
For some reason the index got messed up so that anything in the current index would not show the preview. I figured this out by stopped indexing altogether for a few days and then turned it back on. Once it caught back up, all the new emails have the correct preview. So, I deleted the current index and had it reindex the entire computer and everything is fine now. I just did it Friday night so it wouldn't bog down the computer while I was working on it. I can only speculate what actually caused the issue, but deleting and reindexing should fix it if it's exactly what I experienced.