In 1988, Christian Slater and Winona Ryder starred in Heathers, a film about… well, actually I don’t know what the hell it was about. I’ve never seen it. However, since it is a movie, and it is named Heathers, I can safely make two assumptions. One, there are multiple characters in this movie who are named Heather. Two, at some point at least, shenanigans—and quite possibly even hijinx—ensue.

And that, my friends, is all I need to know to make this an apropos introduction to a man directing his own production in the form of a fantasy team with a cast of characters scripted to include multiple Ryans.

Yes, in my oldest and most expensive keeper league, I am the proud owner of both Ryan Howard and Ryan Braun. The setup for this league is quite simple. It’s a 10-team, mixed league, snake draft league with deep rosters, and you are allowed to keep your five best players as your first five draft picks.

As of the end of the 2011 regular season, I thought I was sitting in pretty good position for 2012. I had a keeper core of Troy Tulowitzki, Braun, Howard, and Nelson Cruz. Battling for the last spot were Victor Martinez, Drew Stubbs and Jered Weaver. My early thoughts centered on packaging Howard and somebody besides Tulo or Braun for another top 10–15 player. Since then, I’ve seen my team crumble from within, several months before the draft.

Last week, I talked through a hypothetical thought process during a draft. This week, we go from the theoretical to actual. Once again, we’re going to take a trip inside my head as I think through how to deal with this mini-crisis. This will be a two-part piece. Today’s column will deal with thoughts about proceeding on the keeper front. Next week, I’ll discuss how these losses might impact my overall draft strategy.

The first relevant point that further defines the context of my keeper dilemma is that this is the final year of a keeper cycle. Entry fees are at their peak, and next year the league will totally re-draft from scratch. So this dynamic answers the questions of whether I should consider keeping either player in spite of their predicted absences.

If this was year one, two, or maybe even three of the four-year keeper cycle, I’d at least keep Braun, anyway. But, I do have at least five players who can be expected to outproduce 110 games from Braun, so that determines decision number one. Howard’s case for being kept is even weaker, so let’s move on.

Now I’m left with a keeper core of Tulo, Cruz, V-Mart, Stubbs, and Weaver. The first thing I must do, or rather not do, is overreact. It is important to take a step back and realize that this is a collection of players that is perfectly capable, though perhaps not likely, of accruing proper value for the top five players on a contending team in a league the size of mine.

Tulo is an upper first-rounder. I’ve said it here before that at some point in Cruz’s career, he’s going to randomly play a full season and put up second-round value. If this is that year, I’m still on decent pace.

Stubbs is always going to strike out too much, and I’m still not sure where the Reds will bat him in the order, but he’s 27 and coming off two consecutive seasons with more than 50 combined steals and homers on top of 90-plus runs. He’s one lucky BABIP or homer rate season away from top-35 production.

V-Mart is among the few catchers with a perennial chance to be the top producer at the position. And Weaver is good enough to be the best pitcher on a fantasy champion. So, the outlook isn’t entirely bleak.

However, there are a few strategic decisions and several possible courses of action to shuffle up this core that are worth discussing. The first option that comes is to mind, which I’d also be able to do without much hassle, is to trade Tulo. The path here would be to improve the overall depth of my core by downgrading my top keeper but upgrading at least two other keepers.

I’m not sure I will wind up doing this, but it is worth trying to test the market. My price will be high. I am not willing to trade an otherworldly player like Tulo, who provides so much value beyond nearly all his peers, simply for two players likely to be a bit better than my fourth- and fifth-best players, respectively. I’d listen to offers that included two top-30 players, and preferably ones that include a player who I’m higher on than the market.

For example, Ian Kinsler is a player who may turn off some because his resume includes multiple seasons hitting in the .250s or .260s. However, I think he has borderline first-round production, so I’d try to find how poorly his owner took Kinsler’s .255 batting average in 2011. If I can get Kinsler and another top 35 or 40 player, I’d consider that kind of deal. But, generally speaking, I’m not in favor of trading a game-changer for two incremental improvements.

Remember, the range of possible production for players in the top 30–50 can be pretty wide. In Tulo, I’d be giving up one of the few players whose expected production is outside the upper percentile projections of the types of players I’d be receiving.

Say I’m offered a package of something like Hunter Pence and Cole Hamels. While those two players may be better, or more highly ranked, than Martinez/Stubbs and Weaver, too large a portion of their universes of predicted seasonal production overlaps with the universes of predicted production for my original pair. Pence and Stubbs are not in different classes, though Pence may be closer to the head of the class than Stubbs.

Mental Health and the CBA
A particular bit of language in the latest CBA could have negative consequences for some players.

Tulo, on the other hand, is in an entirely different class of player than anybody else discussed. I’m not selling my Armani suit to finance the upgrade of my cufflinks and tie clip.

Another question I need to ask myself is whether I want to increase the variance of my team’s potential performance and, therefore, try to make some trades in the keeper stage that will invite more risk. On the flip side, knowing that I may be a bit in the hole already, I may want to play this stage of the game even more conservatively.

If I were going to employ the former philosophy, I may try to trade for players returning from injury, who have bounce back or sustainability questions, uncertainty around their future, or elevated health risks. Some players who fall in some of these buckets include Alex Rodriguez, Chase Utley, Joe Mauer, Shin-Soo Choo, and Lance Berkman, to name a few.

I don’t think I’m going to go this route, either, as most of these players likely can be redrafted, and I’m not gung ho enough about any one of them to target this aggressively, though I do think some of them may make interesting targets on draft day.

Further, this league has a pretty substantial second-place payout, and even third place gets more than his money back, so I don’t want to move prematurely from the “give myself a chance to win” to the “it’s either first place or last place” model of roster management.

If I wanted to go in the safer direction when balancing risk, perhaps I could make a trade along the lines of Cruz for Paul Konerko, where I sacrifice ceiling but likely gain predictability.

Above all, what I want to do at this stage in assembling my team is build around players I believe in. I believe in Cruz’s ability to put up a monster fantasy season. I don’t fully trust it, but I believe in it. I trust Konerko, but I don’t love his value. I believe in outfielders having plus positional value. I don’t believe in overpaying for quite good, but not elite, first basemen who are closer to 40 than to 30.

This question of risk balance will reveal itself constantly as I consider my overall draft strategy, as well. I’ll discuss it more next week.

For now, my tentative plan is to test the market for Tulo and see if I can get an offer I consider a winner. In a marketplace of only the top 50 or so players, the only other player on my roster I could see drawing interest is Cruz, and I totally consider him tradeable, too. I don’t foresee myself making any moves for the primary purpose of altering the risk profile of my top five.

Only a few months ago, I had inked Tulo and Braun in as untouchable and was willing to treat Cruz as a throw-in as part of a deal in which Howard was the centerpiece, and my return would be a player a mere ten spots or so ahead of Howard in total value. Let’s just say it’s been an eventful offseason.

Draft strategy talk coming next week.

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jeffrey gross
jeffrey gross

You should really watch Heathers. A delightful black comedy.