The factors that contribute to the off-season trading of keepers

By Dan Gardner

If you’ve ever played keeper league baseball, you’ve almost certainly been in a situation where you have to play musical chairs with your keepers – too many players, not enough keeper spaces.

Anyone you don’t keep means nothing to you – unless you can trade him.

What goes into a potential keeper’s trade value? In addition to the normal factors contributing to a player’s trade value, the number of keeper spots determines a potential keeper’s trade value to your team.

Let’s use two base cases in the analysis: one keeper slot and multiple keeper slots. Then we’ll apply the general cases to a specific one.

In a league with just one keeper slot, there is little reason to trade. If you have Albert Pujols, there’s no reason to trade him short of differing valuations – for example, you swap Pujols for Hanley Ramirez if you see Hanley as more valuable and your trading partner sees Pujols as more valuable.

In a league with multiple keeper slots, the opportunities for gains are more. However, the pool of “trade-worthy” players is less.

During the keeper decision period, the marginal player (the last player who should be considered for a keeper/roster slot) is far more talented than the marginal player during the season. In a 12-team league with 3 keeper slots, the marginal player is the 36th most valuable player – anyone better has trade value. That leaves quite a few players with no trade value, in theory.

Compared to the regular season, with much deeper rosters and more players who command trade value, trading is more difficult.

However, consider that within a 12-team, three-keeper league, the 36 most valuable keepers are not evenly spread among the 12 teams. If you have Joe Mauer and players below the marginal player threshold, you would be wise to get on the horn with a loaded team and ask for two very good players, as long as you improve your overall group of keepers. (Do not trade him just for the sake of “filling out” your keeper slots with solid players.)

For an example, let’s consider one of my leagues.

At the end of each year, teams can extend the contracts of players signed in the previous off-season (via open bidding) or during the season.

Further, each team has the option of extending one player whose “first” extension contract has expired. My team had four players whose first contract was expiring – Wandy Rodriguez (salary of 0.05), Hiroki Kuroda (3.9), Matt Cain (9.5) and Derek Jeter (10.3). While Rodriguez is merely the third best player in this group in talent alone, salary considerations makes him the most attractive keeper on this list. I started shopping the other three players, hoping for a bite.

Due to the rule of one “second” extension per team, I quickly realized there were only a few teams in the market for a strong keeper – an example of how having just one keeper slot severely reduces incentive to trade.

This league has a salary cap of 100, and while Jeter, Cain and Kuroda are not overpaid, they aren’t making too much less than they would in open marketing bidding.

So I ended up trading Matt Cain for Everth Cabrera, Jeff Francis and Manny Parra (who I can keep as “first” extensions). I have yet to find a taker for Jeter or Kuroda.

This might sound strange, but it’s customary.

While Cain is a good player, he is not a particularly unique commodity in this case – several other teams are hawking extension-eligible players. Another factor driving Cain’s trade value down is that the other manager knows “something is better than nothing” – in other words, from my point-of-view, even Everth Cabrera (making the league minimum) is worth more than an empty roster spot.

It turns out that the value of nothing – a player who you would not keep – depends heavily on the number of keeper slots available in your league. With many keeper spots, don’t fret too much about optimizing your group of keepers. The availability of trades and the increased value of lesser players offer more flexibility in building your keeper group. But if you, like me, are in a league with only one keeper spot, you’d be wise to focus on having the best possible player for that one keeper spot, as your 2nd best player is almost worthless – even if he can be traded like Matt Cain.