Pssst... hey, buddy, I've got a sweet deal for you!
I'll give you two pennies for your one dime. It's twice as many coins, plus, they're bigger and a much more appealing, shiny copper!
We all learned to see through this trick during early childhood, but despite maturing since, little has changed with our perceptions of "volume" deals like this, especially in fantasy baseball. We've been conditioned to reject 2-for-1 trades -- or most any multi-player deal involving a larger number of players on one side -- to a point that many of us won't even read beyond the effort it takes to click the decline button. We are convinced that anything we're getting back is worth no more than two shiny pennies.
We're also convinced that any two teams engaging in such a trade must be dealing in shenanigans; they are almost always the first types of trades that, in a league with a trade-veto system, will raise owners' objections.
Not that this opinion entirely lacks rationale. Most 2-for-1 (and the like) trades favor the side containing the fewest players; logically, consolidating two players into one results in the acquisition of one player of superior ability. But league replacement values and the context of the trading teams' rosters and place in the standings greatly influence these deals, and a generally lax regard amongst fantasy baseball owners for either factor has perhaps transformed these types of swaps into an area of value opportunity.
When to 'trade down' from one to multiple players
Let's begin with the more difficult side of the trade to digest; few owners actively want to divide resources, or "trade down."
Generally, trading down makes the most sense when the team doing it is lacking in depth, making it more sensible the deeper the league gets (12-team NL-only, for example, or a 15-plus-team mixed or greater). After all, the purpose of doing so is to receive a secondary player -- the "second" in a 2-for-1 -- who is considerably more valuable than the players available at the time via free agency, the difference of their values being definitively greater than the difference between the player being dealt away and the primary player acquired -- the "one" in the 2-for-1.
This is where proposing owners on the "2" side frequently stumble: They rarely put in the effort required to consider the roster context of their "1"-side counterpart. This is one of the top reasons such offers fail, and in failing they leave a sour taste with the latter owner that sometimes influences future dealings. Sometimes, these proposals occur immediately after the "1"-side owner's roster has been rattled by a significant, unexpected injury, which is a particularly precarious time to approach said owner.
The best "trading down" deals are generally proposed by the owner dividing resources, especially in the previous example. Only the owner of the team besieged by injuries knows best its need to fill roster holes, and in the event that a consolidating team sniffs such an opportunity and acts first, it's always worth approaching while opening a dialogue with that team. Sometimes, a mere inquiry without a firm offer is worthwhile; with an offer, always assume that there'll be a counteroffer before the final deal.
For the true "trading down" owner, there's an ideal time to strike: When you own a player whose perceived market value is greater than your own opinion, and you can leverage that into swapping for an equally valued player (again, your own opinion) while picking up a second piece to plug another roster weakness. This might be the soft spot in the modern trade market; not many owners think of doing this but with the perception of 2-for-1 trades what they are, those who do so properly are much more likely to complete the deal.
When to consolidate
Next, the more obvious side, and if you do a quick internet search, you'll find countless articles praising the merits of the consolidation trade.
Making this case isn't at all difficult. Consolidation trades make sense when you've got an abundance of resources, some of which you are wasting (generally meaning they're often on your bench). You deal two lesser players for one slightly better player and use the freed up spot to grab the next speculative piece off free agency. This has been a practice used by countless fantasy owners for years, and it's often so telegraphed as to fuel the perception that no 2-for-1 deal is a good one for the "1" side.
Below, we'll get into how to make a reasonable 2-for-1 proposal, but one such strategy that isn't utilized often enough is using this as a way to trade off excess in a particular category while upgrading a specific position or other category. Never, ever waste resources, especially categorical resources. So, for example, a team already strong in stolen bases might tack Billy Hamilton onto a 1-for-1 deal in order to slightly upgrade its first basemen, perhaps from Adrian Gonzalez to Jose Abreu. If Abreu's owner was weaker in steals, Hamilton's addition might be more likely to ease any possible discomfort in the idea of downgrading at first base.
Setting value points for 2-for-1 deals
Doing your homework is paramount in making these deals. We all hate homework, but you can be sure that you won't be successful in trading when you don't do it.
First off, determine your league's replacement value. This is the typical player available on the free-agent list, and in the preseason, it represents the players at zero (or slightly beneath) dollar value when running your league's specs through our Custom Dollar Generator. Each player's trade worth is the effective equivalent of his price tag on that page, making it the easiest time of the year to make such decisions.
But here's the rub: Trade values are also influenced based upon the time of the year that they're made. In a keeper league, for example, trading is significantly different before the cut-down than it is during the regular season. During that stage, the replacement level rises substantially; it instead resides at the point in the rankings that represents your league's total number of players kept. So, if your 10-team league affords 10 keepers per team, then your replacement level before the roster cut-down is effectively the No. 101 overall player (and those beneath). That requires a recalculation, in which you'd need to redistribute the total number of auction dollars on a spreadsheet amongst only the number of total players kept in your league.
Unfortunately, you're not done yet. Making such a trade offer isn't as simple as taking two dollar values you got using the steps above, adding them and picking a player worth the total. That'd be the equivalent of offering the person with one dime two nickels, which is fair, but what's the point of lining your pocket with two coins when one will do?
The idea is to take those values, identify a team with an opportunity to either split resources or consolidate -- depending on which side of the deal you plan to be on -- then adjust those values to fit the other team's needs. Remember, not all teams possess equal resources; there is a reason that certain teams are in first and others last at season's end, and it usually speaks to the distribution of talent on their rosters.
The team in first, for instance, is going to have a considerably higher team "replacement level" than the one in last. The former's least-valuable player might be Melky Cabrera; the latter's least-valuable player might be Jon Jay. That can have as much as a $10 difference in what an incoming player might be worth to those teams, and it's going to have that much influence on those owners' trade judgment.
Using our 10-team construct, let's craft a few examples.
Jose Bautista, at $31 using our Generator's values, might be worth swapping for a $26 J.D. Martinez and a $7 Gregory Polanco during the regular season, especially if you're a Bautista owner who sees his and Martinez's values as roughly equal.
But that deal wouldn't make any sense to the team with an excess of outfield depth, and if Bautista's team had the aforementioned example of Cabrera as its worst player, a team proposing a 2-for-1 deal would need to elevate the offer to something closer to Martinez and a $11 Michael Brantley. Brantley's valuation would represent enough of an upgrade over Cabrera (valued at $5) to be worth consideration, especially since that team could possibly stash Brantley in a DL spot until he's fully healthy.
If it's the pre-cut time in a keeper league, though, neither offer would make much sense at all. Instead, Bautista would probably require Martinez and a much, much more valuable player like Jason Heyward or David Peralta-- or even a Justin Upton or Adam Jones if it's the example of the team overflowing with talent -- in order to get the deal done at that stage of season. While that might sound excessive, remember that players like Heyward and Peralta wouldn't reside far above the cut-off for a 100-players-kept league, and if the team giving them up is facing the prospect of merely cutting one with nothing in return, then the small upgrade from Martinez to Bautista is worthwhile.
Conversely, a team rich in top-tier talent but hurting at the bottom parts of the roster shouldn't be afraid to divide resources; don't fear it when it's called "trading down." If we project 2-3 of your eventual keepers beneath the cut-off, so for example, Lucas Duda and Steven Souza Jr. are your final two choices, it might make sense to swap a Chris Davis for, say, Adrian Gonzalez and Yasiel Puig, in order to clearly upgrade the final places on your keeper list.
The last thing you want to do, after all, is keep any one player who would be noticeably less valuable than players readily available in the draft. It's one thing to do so if it's a young player or one priced extremely favorably; it's another to avoid 2-for-1 or similar trades in fear of making a poor move.
Always -- always -- be on the lookout to upgrade every piece of your roster; the goal is to shift every single spot you've got as far above replacement level as possible, at every moment of the year. Considering the diminishing rate at which people are creatively doing this via the trade market, revisiting an old, seemingly stale strategy and utilizing a new twist might be the answer.