Last year, during my home league draft, I punted shortstop and catcher. Or rather, I deliberately held off drafting them for a long time. I had two players in mind for these positions, Elvis Andrus and A.J. Pierzynski, and was fairly confident after the first 15 rounds that I had them all to myself. The rules in my league were such that drafting two catchers or extra middle infielders over corner infielders before the reserve draft made little sense, at least to me. Of course, other teams had something else in mind and grabbed these players before I was ready to pull the trigger. In the end, I found Ben Zobrist early in the season and all was well at shortstop. At catcher, though, I suffered through Jarrod Saltalamacchia and then worse when he went down. (Eventually I traded with the guy who drafted Pierzynski for the catcher he had drafted early—Geovany Soto. That didn’t work out too well either.)
The moral here, as both Derek Ambrosino and I have written about, is to not let your strategies be too dependent on guessing what other owners are going to do. Of course, a little guessing or empathy is necessary; just don’t go overboard. There’s a bigger reward in better valuations of players than there is in hoping that low-hanging fruit is left undisturbed by the other owners in your league. Here’s a rule of thumb:
1. Get your valuations down pat. If you’re in a draft league, calculate/find out where you think the player should be drafted. If you’re in an auction league, get a dollar value. Glance at average draft positions or some site’s projected dollar values. If you’re way off the consensus, try to find out why. Maybe this will help improve your valuations. DO NOT earmark players that are projected to go much lower (or for less) than you project as players that you can wait long on. These differences may be a result of differences in your league from the average league or recent changes in information about players that stale rankings are likely not to reflect.
2. On draft/auction day, let your valuations guide you. In a draft, if you think you can wait a round more for a player than where you have him projected at, go for it—as long as you don’t absolutely need him. I wouldn’t wait more than a round or so, though. If you pick up a round or two of value (a.k.a. expected profits) on even just four or five players (in addition to any good luck/bad luck profits or losses you might get in the course of the season), you should be in great shape to compete throughout the season. That’s all you can really hope for from a draft. There’s the saying that you can’t win a draft in the first couple of rounds, but you can lose it—I think this applies to much more than the first couple of rounds. Sure, you are more likely to get upside luck with a player that you’ve drafted later (how much good luck could you really get from Albert Pujols, after all). But luck like that is (almost by definition) mostly random, whereas getting squeezed on a position because you waited too long to draft a player can leave lingering holes in your lineup.
In an auction league, matters are slightly different. In auctions, you get expected profits when you draft a player for cheaper than what you had him valued at. Here, the equivalent of waiting too long in a draft league is not bidding (and winning) $11 on Evereth Cabrera even though you had him valued at $15 because you expected to earn even more on Andrus only to see Andrus go later in the draft for much more than you expected. In an auction, the downside to waiting is rather less, assuming you have the budget, since you can always win Andrus if you really need a shortstop.
However, this brings me to a point about auctions: Don’t think too much about when to nominate a player for bidding. That is, don’t waste effort and brainpower, particularly while the auction is going, on if/when to nominate a player. There might be a slight bit of value to be gained by timing a nomination well, particularly if you know your leaguemates well. But an extremely good approximation of the best nominating strategy is acting randomly: sometimes nominating players that you value relatively highly, sometimes nominating players that you don’t care about. This way, you won’t give your opponents any information about how you value the players.