Before your draft, you should understand what players you think are going to be undervalued by others. These are the guys you want to target. For example, if you think Jonathan Sanchez is going to be valued as approximately an 11th round pick*, and you think his talent is worthy of a 7th round pick, it’d be a mistake to draft him in the 7th round. Most likely, no one else is going to be thinking about taking him for another three or four rounds. Therefore, to get the most value out of Sanchez, you should take him in the 10th round (or 9th, if you’re worried). By doing this, you are in essence getting two 7th round picks – the one you actually choose in the 7th round, and Sanchez, who you believe was worthy of a 7th-rounder but you didn’t take until the 10th round.
This strategy also works particularly well for position players, although it’s a little more complicated. Let’s say that you think Rickie Weeks is going to be undervalued, and you’d be perfectly fine with having him as your starting second baseman. Let’s also say that for your first round pick, you are debating between Chase Utley and Jose Reyes. Who should you take? There’s not a huge difference between Utley and Reyes in overall value. But you think that Weeks is going to be undervalued, and that you can “steal” him very late in the draft. If that’s the case, it makes sense to draft Reyes in the first round, rather than Utley. If you drafted Utley, you’d be getting a fantastic player, but you’d also be negating a competitive advantage – namely, your belief in Rickie Weeks being undervalued. By drafting Reyes and saving second base for Weeks later in the draft, you have extracted maximum value.
This strategy is not without risks – it only takes one other person to value Weeks as highly as you for him to be snatched from under your fingertips. Thus, you need a backup plan, a “worst case scenario” plan. If you lose Weeks in the 12th round, are there any other second baseman who are going to be available that late that you think are somewhat undervalued? If so, then they are your backup plan. Or perhaps you’re willing to “punt” second base, and essentially hope to trade for someone or find someone on the waiver wire.
If you can’t possibly think of a backup plan, then you need to be wary of putting all of your eggs in Weeks’s basket. Yes, he may be undervalued, but if you miss out on him your team may be in deep trouble. This is something to keep in mind when thinking about sleepers. However, it’s very rare that your team won’t be able to overcome something like missing out on Rickie Weeks. The advantage of getting a player who is much better than where he is drafted almost always outweighs the risk of missing out on that player and ending up with a scrub instead.
*Note: I am not necessarily endorsing Sanchez as an 11th round pick, or a 7th round pick. I am merely using Sanchez and these numbers as an example, to demonstrate a point.