How to Take Risks in Fantasy Baseball

Flags fly forever. We play fantasy baseball to win our leagues, not to just put together a consistent, above-average team. However, we all are working off similar rankings with essentially equal resources (draft picks, etc) to apply to those rankings. If you select a team based purely off rankings competing against players at similar skill levels, you are probably destined for an average or maybe slightly above-average team.

We all know what owners do to combat this destiny: they look to draft variance. There are “safe” players, who offer a reliable but modest return for their price, and “risky” players, who are more volatile, but have a better chance of returning a higher value than their price.

The player who wins your league is going to have to get a little bit lucky. A team full of low-variance players has a lower probability of being the #1 team in your league in any given year. Therefore, you need a variance strategy. A lot of fantasy players do this wrong. Here’s how you can do it right.

Bad Strategy #1: The Risk Taker

You’ve probably played with The Risk Taker before. The Risk Taker loudly proclaims to everyone in the draft that “She’s going for broke”, or something similar. She’s not interested in any safe, boring players. She reaches for high ceilings. After the first 7 rounds, her team looks something like this:

SP: Noah Syndergaard
SS: Alex Bregman
OF: Nomar Mazara
2B: Rougned Odor
SP: Alex Reyes
OF: Manuel Margot
SP: James Paxton

The Risk Taker looks at her team, and says, “Damn, I’ve got seven potential first round picks right here! Maybe it’s risky, but if everything clicks, I win a championship!” The problem is, she doesn’t understand conditional probability.

It is true that all of these guys have huge ceilings, and you pay for those ceilings by taking on a lot of risk. If they all reached their 100% projection, Team Risky Taker would be one of the best in the league. However, the probability of Noah Syndergaard and James Paxton pitching 200 innings AND Alex Bregman, Manuel Margot and Nomar Mazara breaking out AND Alex Reyes coming back 100% AND Rougned Odor learning how to be a real hitter all at the same time is very, very small. Sure, if they all click, she gets a superteam, but by relying on so much risk, she ends up average more times than not.

Any casino owner will tell you the same thing. A roulette player has a decent chance of winning any given hand, but has almost no chance of winning over a long string of bets. Every time you take a risk, your average luck regresses to the mean.

Bad Strategy #2: Mr. Safety

Mr. Safety does not like The Risk Taker. He knows that her strategy is doomed to fail most of the time. So, he over-adjusts. He only takes safe players at full price. Every single season, Mr. Safety either just barely makes the playoffs, or just barely misses it. After five rounds, his team looks something like:

OF: Mookie Betts
2B: Brian Dozier
SP: Madison Bumgarner
1B: Jose Abreu
SP: Jose Quintana
SP: Chris Archer
C: Salvador Perez

Mr. Safety’s team is boring. Everyone was drafted at their proper position, but no one has much room to grow. His probability of being the best team in the league is pretty much zero. Maybe he’ll take a few Hail Mary picks at the end of the draft, but he’s not going to spend valuable draft picks on lottery tickets. Of course, those Hail Mary picks are available at the end of the draft are available because they are extremely low probability.

Mr. Safety never wins because he never truly plays.

Good Strategy: The Tight-Aggressive Player

In poker, players often categorize other player on two dimensions: how frequently they play hands and how aggressively they bet when they do. A loose-passive player enters a lot of hands, but will fold to a bluff. A loose-aggressive bluffs constantly. A tight-aggressive play style is generally considering the optimal strategy: enter few hands, but bet aggressively when you do.

The Tight-Aggressive Player often looks like Mr. Safety. Most of the time, he’ll take safe bets at full price. However, once he builds a base portfolio, he takes a big bet. His first several rounds might look like:

OF: Mookie Betts
OF: George Spinger
3B: Vlad Guerrero Jr.
SP: Carlos Carassco
SP: Jose Quintana
2B. Whit Merrifield
SP: James Paxton

Team Tight-Aggressive picked up two strong, young, safe all-around players in the first two rounds. Given the base, the Tight Aggressive Player felt comfortable taking one of the best prospects in the third round in Vlad Guerrero Jr. By taking Guerrero, he creates a bit of a hole in his lineup for the next year or two, as Guerrero hasn’t yet hit Double-A. He follows it up with two safe-ish, strong starting pitchers, and a medium-risk Whit Merrifield. Finally, he takes a risk on James Paxton, who could win a Cy Young if he stays healthy but has a long history of injuries.

In the short term, this team will look to ride James Paxton to one of the best pitching staffs in his 20-team league and strong all-around production from his core hitters. He can contend even if Vlad Guerrero Jr. busts, although the team won’t likely be truly elite unless any time soon he becomes a star.

In our TDGX2 draft, I used a similar strategy. Drafting 11th in a 20-team league (5×5, but with OBP and SV+HLDs), here were my first ten rounds:

1B Freddie Freeman — Safer
3B Anthony Rendon — Safer
SP Stephen Strasburg — Safer
SP Aaron Nola — Riskier
OF AJ Pollock — Riskier
SP Luis Castillo — Riskier
RP Felipe Rivero — Safer
2B Robinson Cano — Safer
OF Lorenzo Cain — Safer
SS Jorge Mateo — Riskier

Each of the top three picks is pretty safe. Freeman and Rendon are in the prime of their careers and are coming off career years, solid bets to combine for 200 runs, 200 RBIs, 50 HR, and a .400 OBP for the next few years. Strasburg was, in my rankings, the end of a starting pitcher tier. While I was happy with the value that I got Strasburg at, I don’t expect him to be much better than he was last year.

Then, I got a little more adventurous with Aaron Nola in the 4th round. Nola has ace potential, but is a young pitcher on a bad team, and a safer option in Carlos Carassco was available. AJ Pollock is a medium-risk, medium-reward player: older and with a recent history of catastrophic injury, but also a decent bet for 20/25 with 100 runs.

I regard Luis Castillo in the 7th as my big move in the draft. Pitchers like Dallas Keuchel, Jake Arrieta and Zack Greinke were still on the board in the 7th. With Strasburg and Nola on my roster, I probably didn’t need to pick up a starting pitcher. But Luis Castillo has even more elite potential than Aaron Nola; he was top-10 in xwOBA by starting pitchers last season.

However, now my team was both a little bit risky, and slightly unbalanced in favor of starting pitching. I took Felipe Rivero to lock down at least one closer for the next three or four years in the 8th, and then two very safe hitters in Robinson Cano and Lorenzo Cain. Finally, I took a risky, super high ceiling prospect in Jorge Mateo.