Fantasy Mailbag: Strategic Thinking

Question: 12-team keeper where we keep between 4-6 at the top of the draft with no restrictions; we can keep these guys forever. I'm already out of the running this year, so I've already sold most my team for draft picks or keeper upgrades. Here's who I've got: Robinson Cano, Joey Votto, Giancarlo Stanton, Prince Fielder, Starlin Castro, Jordan Zimmermann. The rest of my team is pretty much waiver wire fodder.

Since our league has a 1400-inning cap that nearly every manager maxes out, I'm concerned about Zimmermann's keeper value since his K/9 doesn't stack up with other aces in what is essentially a K/9 league. I have an offer proposed to me and considering if it will help my team long-term:

I give: Prince, Zimmermann, 15th-round pick

I get: Kershaw, eighth-round pick

On the surface, it seems to be better for him, but this trade would commit me to keeping five, not six, so I have to figure the value of that sixth player into the mix. To give you an idea, the first players drafted after keepers were done last year were Darvish, Wainwright, Altuve, Scherzer, etc. After this deal, I'd have four additional picks in the first three rounds of our draft: one in the seventh, two in the eighth and one in the ninth.

I see that Prince and Kershaw are side-by-side in your latest dynasty rankings, but with the roster I have, especially Votto, Cano, and Stanton, I feel Kershaw might be a slightly better anchor with the added benefit of being a little younger and likely to produce for a longer period of time.

Additionally, I have another offer that simply ships me a ninth-round pick for my 25th-round pick in exchange for Zimmermann, but that would leave me with five hitters going into next season. Do you see that as a problem in this setting? It's the pitching, along with Castro sucking and Stanton getting hurt, that tanked my chances for this year.

Which direction would you go? Prince trade, Zimm for a pick trade, or stand pat?

Additionally, what the hell do I do with Castro? My instinct is to just ride it out at least for one more season. Too young and talented to give up on in this format IMHO, but ready to be convinced otherwise.

Answer: I like the first trade more for you. Castro stinks this year, but he's too talented to stay this way. Just write off this year as a learning experience for him and hope for better results next year.

Question: I've got a trade offer currently on the table that I've been mulling over this morning and was wondering if I could get some advice on it. I've been offered Bryce Harper and Jimmy Rollins for Jay Bruce and Ian Desmond. I've been leaning toward accepting since Harper is an improvement on Bruce in all of our categories, and hoping that Rollins can have a better second half. I'm just a bit hesitant because of the injuries Harper has been dealing with and thinking that the upgrade from Harper to Bruce may be offset by the downgrade from Desmond to Rollins. Am I overthinking this, and should I sell high on a streaking Bruce to take the stud?

Answer: This is a nice discount for Harper given his injury. I think you'd be paying a decent bit more if he'd been healthy all year and was doing his normal raking.

Question: After listening to the podcast this week, I semi-jokingly offered a team Puig for Carlos Gomez. They rejected but did counter with Pence. I know he's not a "sexy" pick, but when I checked his exact stats, he and Carlos Gomez are actually closer than I realized: Gomez – 43/12/37/15/.313, Pence – 46/12/40/13/.292. Think Pence keeps it up and Puig comes way down? I'm pretty stumped by this trade. Everyone in the group commented basically to keep Puig, but I don't see it that cut and dry. Thanks!

Answer: That's really not a bad counter because, as you mention, Pence has been rather Gomezian. However, I still feel like he can net more either within that deal (get a little throw-in) or elsewhere in another deal.

Question: I’m trying to buy low on Verlander, who I think will be fine the rest of season. Question: Is Max Scherzer too valuable to trade for him?

Answer: That's a premium price to pay for him. You should be able to do it a bit cheaper than that. If you can’t, then let pass.

Question: What do you think of Matt Barnes? I have an offer on the table to deal Melky ($18) and Detwiler ($1) for Blanks ($8) and Barnes ($3, minors). I would activate Gibson and put Barnes in my minor-league system. TINSTAAPP, but does Barnes have enough value to take the downgrade from Melky to Blanks?

Answer: You can do this since it means activating Gibson, someone both myself and Paul like.

Question: I currently have an offer on Miggy where I would receive Harper and Kershaw for him. I need pitching help, and this league is a 12-team six-keeper league. You can keep a player as long as you want with no penalties or salary or anything like that. This move shouldn't hamper me from contending this year, as I have a strong offense but an average at best pitching staff.

Are Harper and Kershaw in this format enough? Its also an OBP and Quality Start league, so if anything, I would assume that helps Kershaw's value. I'm having a real hard time wrapping my head around dealing Miggy, but I keep getting offers, so I figure I should at least be open to it.

Answer: It's absolutely enough. I'm not sure you'd get the offer if Harper were hurt, so I'd definitely do it.

Question: Hey guys, I'd love to hear some discussion around strategic thinking as we near the midpoint of the season. On the FB page, I see a lot of discussion around "is this trade fair," "who wins this deal," "will player X outperform player Y," etc. IMO, at this point in the season, every move should be evaluated by how it will impact each roto category, and thus the standings. "Winning" a deal is unimportant; winning the league matters.

I think there could be a very productive half-hour discussion on strategic thinking depending on your place in the standings. If you're middle of the pack, what should be your focus? If you're lagging behind, how do you make the determination of when to start trading for keepers? If you're leading the league, how do you keep your edge and project realistically to stay out in front?

A quick example. I'm 30 points clear of second place in my 13-team mixed roto keeper league. Barring injury my projections have me winning the league comfortably. Last week, I traded away Gerrit Cole in a package for Joe Mauer. Now, I just called up Zack Wheeler and am trying to think strategically here. With no obvious holes, I'm tempted to try to win the league AND hold Wheeler. But, of course, flags fly forever, and I could get a nice return if I shopped him. How would you approach this type of decision?

Answer: There is an inherent issue with every trade question and it's simply a lack of information. So you're right, someone could be showing us a "winning" trade where he deals Nate McLouth for Robinson Cano, but if he doesn't include that he's mid-pack in SBs where five SBs would get him four points, we won't know that the trade is actually a total dud for him. It's definitely worth discussing.

Regarding your situation, I don't see any reason to trade Wheeler right now. I'd sit tight and see how things go. If you're starting to get uncomfortable in August, then you can move him.

Question: I have a pitching staff of Scherzer, Darvish, Shields, Sale and Greinke. Didn’t pay for saves but have managed to stream a few guys and trade here and there and am sitting third in that category. Currently I only have Brothers as a fill-in. It is a Yahoo league with Wins, Losses, SV, ERA, K, HR allowed, BB, TB, WHIP, QS as categories.

Should I sell on Max? Could I expect one of Fielder, Reyes, Tulo in return? Or should I look for more?

Answer: You can sell him, but you should definitely ask for the moon without fear. He's been arguably fantasy's best SP this year.

Question: I'm in a deep, NL-only keeper league. We can keep 15 major and five minor-league players each year. I have Oscar Taveras and of course everyone wants him. I have been offered Anthony Rendon, Albert Almora and Marcell Ozuna for him. Looks like a fair offer but I hate to give up Oscar. I have held Oscar for three years and don't want to give him up just before he explodes on the scene. One more bit of info, I also have Zimmerman and Espinosa so Rendon would fill my 2B hole and provide coverage if Zimmerman gets moved off of 3B.

Answer: I'd hate to give Oscar, too, but that is a really legit offer. I know this isn't too helpful, but I'd understand if you said yes or no. This is the part where fun/playing favorites/bias creeps into fantasy and it's not necessarily a bad thing. Personally, I think I'd go ahead and do it.