Having completed an AL only auction last Saturday and an NL only auction two Saturdays ago, I have three takeaways/learnings to discuss to help us (read: me) in future auctions. They are not big enough to be their own article, but their weak connection is strong enough to form an article. Please find these three takeaways below:

1. Don’t fear the endgame

A mistake I made when I first started doing auctions was making sure to have several (more than one) dollars per player available for the last couple of players that would fill out my roster. After watching many of my leaguemates end up with great $1 and $2 values, I realized there was a flaw in my process. At its core, I was allowing fear of uncertainty—something other than value—to influence my decision making process. This gets even more costly when our leaguemates make the same mistake because those endgame bargains that you were planning on scooping up when others only had a dollar or two left are no longer bargains when others have money saved up too. Not only did we end up taking less valuable players at the top of the auction, we are now overpaying (or at least not getting discounts) for players at the bottom of the auction.

The key here is to know what is going to be left at each position. Obviously, with utility spots and multi-positional eligibility there is no way to know with certainty, but we can at least know a range of outcomes. Once we know this range, we can determine which end game positions we like best and plan accordingly. We should not be passing up on great values earlier on at a particular position just because we like the players that will be there at a dollar, but in a tough auction this can help us figure out where we want to be aggressive and when.

Lastly, the added bonus of having a couple of $1 players to take at the end of the auction is that your endgame players are not necessarily your leaguemates’ endgame players. Put differently, there is a smaller chance than we probably think that the $1 relievers you are targeting for your last pitching spot are the same $1 pitchers your leaguemates are targeting. It is smaller than we think because of projection bias, which states that we overestimate the degree to which others think what we think. Consequently, we often plan for auctions assuming that all players will go as we think they will, even though they never do. This means that the players that you wanted to save $3 for might be available for $1 anyway. When we combine this with the fact that these players are likely to be your first cut/least productive players to begin, it becomes important not to let these fears get in the way of acquiring better, higher tier talent earlier in the auction.

2. Getting the money out

When nominating a player, the goal should either be to (i) nominate a player that your leaguemates will most overspend on or (ii) nominate a player that you can get at value or at a discount. While nomination strategy has been discussed previously, nominating the best player left at a position, although obvious, warrants further explanation here. In the past I have advocated for throwing out the last player available in a perceived tier, which fits the best-player-left-at-a-position framework, but circumstance does not always allow us to do so. In the instance where there is no best player left in a tier available to throw out, throwing the best player available (even if lesser players are available in the tier) is probably the next best tactic for getting the most money out. Why? Because even though the player you are throwing out might not be at the bottom of your tier, it might be at the bottom of some of your leaguemates’ tiers. Again, we need to be cognizant of projection bias and make sure that we do not assume that everyone thinks like we do.

3. Don’t buy into your own genius

The flipside of projection bias (of overrating the degree to which our leaguemates will think like us) is our ability to overestimate our own uniqueness and ingenuity. We have all been there, having come up with an idea we thought to be revolutionary, maybe a business model that was going to make you rich, only to search the idea on and find that it already existed. Similarly, we often go into an auction with some great insight, usually some undervalued player that we are going to get at a great price, only to find that a few of our leaguemates have the same thought. At best, we avoid overpaying for these players that end up going for more than we thought. At worst, we pass up on opportunities elsewhere in the auction and are now forced to overpay for the targeted or remaining players. The solution here is not to avoid having players you like, but to build that into your prices and draft accordingly. If you are the high person on a player, your valuations and consequent bidding will confirm that. If not, you should be happy to pass on a player who is going for more than they are worth. More importantly, being strategically agile and focusing on values gives us our best chance at grabbing the most production in any auction.

Lastly, stay hydrated. These can be long, mentally taxing events, and your body can always use the water.

Thank you for reading

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Have you ever been in a league long enough that your previous successes impact your approach to the endgame? In my long term 14-team mixed I have a reputation for snatching up cheap pitchers before their breakout season. I'm finding it harder and harder to land any $1 pitchers in their 20s. I consistently get bid up and cannot afford the jump from $1 to $3. Keeper value is also diminidhed at the $3 price. Should I be throwing my diamonds in the rough earlier in the draft to try to slip them through or just vere away from the breakout pitcher roulette wheel altogether?
in these cases I think there are 2 possible approaches-- either throw them out much earlier, when there are a lot of better options available, or wait until literally no one else has the money to spend.

Both these options require knowing more about the other teams, and having enough guys on your list that you can afford to miss several of them. But I think if you're looking for $1 players, you have to be looking at value independent of position. If the $1 pitchers are actually going for $3, then start looking at the $1 hitters or throwing the $1 at prospects likely to jump higher in top prospect lists over the year.
Yes agreed. And this goes back to knowing which positions you like the end game values the most and least.
I have a similar problem. This year lost out on a $1 deSclafini in NL only because one of the habitual bottom owners figured my $1 pick was better than his $1 pick.
I think successful strategies definitely get copied in longstanding leagues. When this happens, you can try and throw out these guys, but I'd be happy taking values in the mid and higher tiers while everyone holds their money back for the endgame.
on getting the money out-- when throwing out a player, it's equally important, I think, to be aware of the competition. When it's a first year auction and everyone has the same budget, this is less important or at least not relevant until near the end of the auction. But for auctions in keeper leagues, teams will come to the table with different amounts of money AND different holes to fill. If you're going to nominate a player, it's important to know who might bid for them and how much they might be willing to spend.

Coupling this with the first point on the endgame, I think it's important to realize that you can always afford to spend the extra $1 on the player you really want. I very very rarely nominate the player I actually want, especially for the stars of a team, and try to enter the bidding late so that I have a sense of who is in the action.

I think the most important rule, though, is that if anyone is set to 'auto' for the auction, just throw your prices out the window and recognize that they will be spending face value on any player regardless of position. They're just the worst.
If there's a player that I really want in the end game, I usually start them at a $2 bid (we can do that in our league). You are much less likely to be topped with $3 than with $2, as other teams a) Don't want to spend the extra money and b) assume that you'll go over them at $4.
Strategy during an auction, based on my 26 years experience of making mistakes, coming up with odd theories, and watching my leaguemates, is something that occurs in phases and evolves.

The phases typically include "toss out the best player available who will suck the most money out of the pool", followed by "drain talent where I have excess or at least sufficiency", and finally "control who ends up on my roster in Dollar Days". The evolution comes into play when deciding when to shift phases, how hard to push phase 2, and when to sacrifice control over the endgame in favor of avoiding a phase 2 issue caused by one of my competitors.

Lock into a single strategy at your peril; there is no "one size fits all" in competitive leagues.
Absolutely. You have to be able to pivot/be agile, otherwise you'll always be at the mercy of others.