Roster Doctor on keeper trades

Chris writes in:

I’m in a 12-team mixed keeper league with the standard 5×5 roto scoring, with the exception of OBP instead of AVG.

We can keep two players while surrendering the draft round they were selected in. I have:

Buster Posey (Undrafted)
Francisco Liriano (18th Round)
Justin Upton (7th Round)
Colby Rasmus (Undrafted)
Stephen Strasburg (14th Round).

I was given an offer of Ryan Braun for Posey. I need to trade away some of this talent because I’m in second place with a small chance at first. I don’t want to finish the season with all of this keeper value unexploited. Whom do I keep? Trade? Undrafted players are kept by surrendering the last-round pick. Thanks.

Roster:
Geovany Soto C
Ike Davis 1B
Juan Uribe 2B
Evan Longoria 3B
Stephen Drew SS
Justin Upton OF
Colby Rasmus OF
Jason Kubel OF
Carlos Pena Util
David Wright Util
Michael Bourn BN
Buster Posey BN
B.J. Upton BN
Dustin Pedroia DL

CC Sabathia SP
Francisco Liriano SP
Francisco Rodriguez RP
Ryan Franklin RP
Alfredo Simon P
Johnny Cueto P
Drew Storen P
Aaron Heilman P
Zack Greinke BN
Max Scherzer BN
Stephen Strasburg DL

Chris – I think you are absolutely right to look to sacrifice some of next season’s value in order to win this season. Always do whatever it takes to win this season if you’re in a position to capture the trophy. What you must decide (since I don’t have the information) is where you are best placed to make up points on the leader.

Braun could certainly help you, replacing Rasmus or Kubel in your outfield (note: if you’re unable to pull off the trade, I’d think about playing Posey over Rasmus or Kubel or Soto now anyway, depending on the matchups). I’d just make sure that there are points to be had in your league in home runs or RBIs or maybe OBP. (Also, Pena is much better in your league, with OBP, obviously.)

Another strategy you may want to consider instead, or in tandem, is to trade, say, Bourn to a distant rival for peanuts if that team is in a position to steal some points (all puns intended) from the first-place team. Your bench players can be helping you win by playing for other teams. (Actually, if you can really spare the starter, you could do the same with him, too.)

Also, I’m guessing there are probably more than a few owners willing to consider trading this year’s talent for next year’s hopefuls. Braun is great, but you also have a decent-sized hole at first base. There are quite a few upgrades over Ike Davis, especially if you need help in OBP. Maybe you can pry loose Mark Teixeira or Miguel Cabrera, for instance, instead. You can still keep Davis in the lineup in the Util spot if you feel like it.

Finally, if you had unfettered choice over which keeper to trade for a “Braun”, I would choose Rasmus. Upton, even with his already high draft slot, should be worth enough next year to make keeping him pay off; and in any case, you’ll need him for the rest of this season. Liriano is actually turning in a quietly good season (after so much hubbub was made of him in the Spring Training, not enough is being written about how good a season he is actually having). And Strasburg, well, even with his recent DL stint, I think he’ll be worth a 13th round pick next season. But if you get an owner willing to trade you even more than Braun for him, I would consider it. Right now, if I were drafting for next year, I’d peg him at no better than a sixth- to seventh-round pick. We know he is quality, but we don’t know if he is quantity.