Loading scores...
Draft Strategy

The Greatest League draft

by D.J. Short
Updated On: May 13, 2020, 11:29 pm ET

“The Greatest League” draft is officially underway. In case you missed the introduction of the concept last week, the general idea is to draft the best individual seasons of the rotisserie era, dating back to 1980. We intend to sim out a full 162-game season on WhatIfSports over the course of several weeks. The winner will be determined by the fantasy stats (standard 5x5) accrued in those games.

The league will consist of 20 teams with 25-man rosters. The universal DH will be utilized — sort of like a UTIL spot in a fantasy league — and teams must draft at least four starting pitchers and four relievers.

Players can only be drafted once, so you won’t find Barry Bonds (Giants) on one team and Barry Bonds (Pirates) on another. Eligible players include position players who qualified for the batting title in the season in question (catchers are the exception with a 400 PA min.), starting pitchers who qualified for the ERA title, and relievers who made a minimum of 60 appearances.

We want to be as fantasy-centric as we can with this sim — which is why we are focused on the categories as opposed to team wins and losses — but defense also matters in how it impacts run prevention for pitchers.  

With that out of the way, take a look at the crew we have assembled for this league, organized by draft order. Brad Johnson was the lucky winner of our randomizer. Give them all a follow if you haven’t already.

Brad Johnson (@BaseballATeam)
Christopher Crawford (@Crawford_MILB)
Nick Doran (@RealNickDoran)
Mike Gianella (@MikeGianella)
Rudy Gamble (@rudygamble)
Chris Towers (@CTowersCBS)
Drew Silva (@drewsilv)
Andy Behrens (@andybehrens)
Matthew Pouliot (@matthewpouliot)
Tim McCullough (@TimsTenz)
Brent Hershey (@brentHQ)
Seth Trachtman (@sethroto)
Alan Harrison (@TheFantasyFix)
Jesse Roche (@jaroche6)
Nate Grimm (@Nate_Grimm)
Scott Pianowski (@scott_pianowski)
Patrick Daugherty (@rotopat)
D.J. Short (@djshort)
David Shovein (@DaveShovein)
Ryan Boyer (@RyanPBoyer)

The draft began Monday at noon ET and we’ve been moving along at a deliberate pace thus far. Since this isn’t your typical fantasy draft, it takes a little more in the way of research and reflection. Besides, this is a fun way to occupy some time with little else going on in the sports world. Below you'll find the draft board as well as analysis of each round. Each of the competitors were gracious enough to provide their insight on their first-round selections. Enjoy and stay tuned for much more in the coming days and weeks.

Editor's Note: If you're on the hunt for rankings, projections, tiers, auction values, mock drafts, strategy and advice on how to dominate your drafts, check out the all-new Rotoworld MLB Draft Guide. Now mobile-optimized with a new look and feel, it's never been easier to take our award-winning advice with you to your drafts for that extra competitive edge! Click here for more!

Round 1:

1.1 Barry Bonds (2001) - OF

Johnson’s analysis:

With the first pick, I quickly narrowed down the choices to either 1999 Pedro Martinez or one of many Barry Bonds seasons. Rickey Henderson rated a distant third. When I examined the pitching and hitting pools, I determined peak Bonds was more advanced from other elite hitters than peak Pedro was to top pitcher seasons. With Bonds selected, it was a matter of choosing which season I wanted. There were several candidates, but I opted for his record-breaking 2001. This campaign was one of his worst in the field which my pitchers won't appreciate. However, immense power output - this Bonds season is the highest ISO in the talent pool by over 80 points - with natural OBP skills will make for a wonderful foundation to a roto-based offense. He even stole 13 bases!

1.2 Larry Walker (1997) - OF

Crawford’s analysis:

Having the second pick was almost a burden, because there are so many incredible seasons to choose from. Ultimately, it was impossible to pass on Walker and what he did in 1997. Not only did he hit .366/.452/.720 in his MVP season, he also added 49 homers and 33 stolen bases. Simply put, this was the best season I saw that combined hitting for average, hitting for power and providing value with steals. All due respect to the names that went after, but Walker was the top guy on my board for good reason.

1.3 Rickey Henderson (1990) - OF

Doran’s analysis:

There were lots of great options to consider with this pick. I wanted to take Henderson to separate my team from the pack in the stolen base category. My first impulse was to take Rickey’s 1982 season because he swiped a record 130 bags that year, but upon closer inspection I realized his .267/.398/.382 slash-line would be a dud in a simulation league. Henderson stole 100-plus bases in three out of his first five seasons but it wasn’t until later that he transformed himself from a pure speedster into an all-around offensive superstar. I discovered his fantastic 1985 season when he slashed .314/.419/.516 with 80 steals and 146 runs scored. And then my eyes bulged when I saw his 1990 campaign: Rickey slashed .325/.439/.577 with 65 steals, a career-high 28 bombs and 119 runs scored. His 190 wRC+ that season was one of the top-25 wRC+ scores for any player from 1980 to the present. Combine that elite slash line with 65 steals and you have a no-brainer first-round pick in this simulation format.

1.4 George Brett (1980) - 3B

Gianella’s analysis:

I figured Bonds wasn't going to slide to me at #4 overall and otherwise there wasn't an obvious pick at this slot. I thought about Pedro (who Rudy Gamble took right after I did) but in the end couldn't pass on one of the best third base seasons in the last 30 years. Outfield and first base in particular look very thick but Brett's 1980 stands out, particularly when contextualized across eras.

1.5 Pedro Martinez (2000) - SP

Gamble’s analysis:

This draft provides an interesting opportunity to think about strategy from a fresh perspective. While pitching points are worth 50% of standard roto points, starting pitching tends to be discounted vs hitting because 1) Starting pitchers have more injuries, 2) Starting pitchers are perceived to be a greater risk to underperform and 3) They are limited to 4 category contributors. In this format, however, all three of these discounting factors are null. Starting pitchers will not get injured. There is no greater risk at underperformance because the sim locks in the skills observed that year. Lastly, since starting pitching helps your sim team win more games than any single hitter, they contribute in the Saves category by creating more Save opportunities. Through that lens, I treated Hitters and Starting Pitchers as close to equal and Pedro Martinez's 2000 season is the second most valuable player (Barry Bonds #1) based on my best understanding of how the sim will work. The fact that 10 more SPs were off the board by my 2nd pick (pick #35) suggests I was not the only one that emphasized SPs a bit more than usual.

1.6 Jeff Bagwell (1994) - 1B

Towers’ analysis:

It’s hard to argue anything about a Hall of Fame career could be overlooked, but I’m not sure if Jeff Bagwell’s offensive dominance in 1994 is quite appreciated. It was downright Bonds-ian — his 1.201 OPS is the seventh-highest in the 1980-2019 era, and four of the six above him are Bonds seasons — obviously those were off the table. He had power and speed, a historic batting average, and was even a Gold Glove defender to help my pitching staff in the sim, for what that’s worth. This is one of the best 5x5 seasons on the board, and was an easy call even this high.

1.7 Todd Helton (2000) - 1B

Silva’s analysis:

Helton was an absolute force during the 2000 baseball season, slashing .372/.463/.698 with 42 home runs, 147 RBI, and 138 runs scored in 160 games played for a Rockies organization that came into existence just seven years prior. It’s remarkable, given those numbers, that he finished only fifth in the National League MVP balloting, behind Jeff Kent, Barry Bonds, Mike Piazza, and Jim Edmonds. I suppose the Coors Field Effect is to blame -- it gives but it sometimes takes away, at least when it comes to awards voting. Grabbing a pitcher is something I considered, and I also thought about a number of speed options, but I figured I could wait a while to focus on stolen bases given how aggressive players were on the basepaths in the 1980s and 1990s, at least compared to modern day. Helton’s thin-air-aided 2000 campaign puts my roster in a very good place from a power production standpoint.

1.8 Frank Thomas (1994) - 1B

Behrens’ analysis:

Thomas, in his prime, may have been the greatest right-handed hitter of all-time. Not ballplayer, but hitter. He also might be the greatest organically grown hitter of my lifetime. During the best seven-year stretch of his career, from 1991 through 1997, Thomas slashed .330/.452/.604. He was at his absolute peak in '94, a season that unfortunately never had a proper end because of the work stoppage. That year, Thomas hit an absurd .353/.487/.729. Those numbers would fit perfectly among the best years of Bonds or Williams or ... well, anyone. If you extend Big Frank's power production from '94 over a full 162 games, he finishes with 54 homers and 49 doubles. I'll happily take that from a guy reaching base at a .487 clip.

1.9 Clayton Kershaw (2014) - SP

Pouliot’s analysis:

When I found out I'd be drafting ninth, my first hope was to land Bagwell's 1994 season. Once that came off the board, I was eyeing Big Hurt's 1994 -- subsequently taken eighth -- but also taking a serious look at the pitchers. Since only Pedro had been picked, I had my choice of the best that Clayton Kershaw, Roger Clemens, Randy Johnson and Greg Maddux had to offer. Still, in my eyes, it really came down to Kershaw or Dwight Gooden's marvelous 1985 season. I thought Kershaw's 2014 was the way to go. His 197 ERA+ doesn't stand out against the other top pitching seasons, but his 1.81 FIP was the third best mark in the player pool, behind only Martinez's 1999 and Gooden's 1984. Throw in the 32% strikeout rate, and it seemed like the best all-around season available.

1.10 Alex Rodriguez (2007) - 3B

McCullough’s analysis:

My first-round goal was very simple. I wanted a five-category contributor at a position where one doesn’t find many such players. After sifting through the list of draft-eligible players, it appeared to me that one of the corner infield positions would be the best choice. Admittedly, I didn’t even consider catchers for the first round. I queued up Jeff Bagwell at 1B and Alex Rodriguez at 3B as my two potential choices with the 10th pick. Since Bagwell was drafted sixth overall by Chris Towers, I ended up taking the 2007 version of A-Rod. I considered taking 1998 Rodriguez since he hit 42 home runs and stole 46 bases that year, but in 2007 he had 52 more Runs plus RBI and hit 54 home runs. I figured it was better to take all that extra production in three categories and look to add more stolen bases later.

1.11 Mark McGwire (1998) - 1B

Hershey’s analysis:

McGwire has the lowest batting average of the first round hitters at .299, but his OBP (.470) and power (70 home runs; .752 Slg) are obviously of great appeal. As so few of us have played this WhatIf simulation, it’s a bit unknown just how to best weigh the player’s final stats in attempting to pick out the roster—which of course adds to the intrigue of this exercise. But at this point in the first round, McGwire’s massive power outweighed some of the more “complete” seasons of players still on the board. So now, I just gotta get some baserunners on ahead of him in the lineup.

1.12 Sammy Sosa (2001) - OF

Trachtman’s analysis:

While we're measuring this draft based on roto categories, I feel that if I build the best sim team everything else will work itself out. With that strategy in mind, the best player on my board was clearly Slammin' Sammy. The 64 home runs stand out, but among the players left on the board Sosa's 203 OPS+ in 2001 was the best remaining of the 40 seasons. Piggybacking Sosa with Jason Giambi from that same epic 2001 season puts my lineup in a great spot to pile up RBI and runs. For what it's worth, Sosa posted 160 RBI and 146 runs that season, leading the league.

1.13 Randy Johnson (2001) - SP

Harrison’s analysis:

The first round turned out to be pretty chalky despite a new format to many. Admittedly, thoughts of Ricky Henderson and Alex Rodriguez crossed my mind from the 13th spot in the draft. I was very wrong to assume they could slide (you know what they say about assuming, right?) Henderson fell off the board third overall while Rodriguez slid a bit further to 10th. And with 10 bats and two arms selected, I felt selecting an Ace like 2001 Randy Johnson would be the best fit to anchor the staff and get the team started in the right direction. The Big Unit's 2002 season was also a possibility, but in 2001 Johnson posted a 2.49 ERA (2.13 FIP), a 1.01 WHIP and fanned a whopping 372 batters (Johnson owns the top five single season strikeout totals in this given time frame). His 13.41 K/9 was good enough for a 30.3% K%-BB% - a career best for the southpaw. 2019 Gerrit Cole and 2002 Vladimir Guerrero were also in consideration, but glad to select the five-time Cy Young award winner and Hall-of-Famer to team "When Doves Cry."

1.14 Mike Piazza (1997) - C

Roche’s analysis:

Piazza's 1997 season is not only by far the best offensive season for a catcher from 1980 to 2019, but the best of all time. His production dwarfs all other catchers. Incredibly, Piazza slashed .362/.431/.638 with 40 home runs, while picking up 201 hits and playing in a robust 152 games. This type of offensive season (173 DRC+) rivals the top seasons across all positions. Meanwhile, the difference between Piazza and the replacement value catcher is massive--far greater than the difference between any other top positional talent, absent, of course, Barry Bonds.

1.15 Gerrit Cole (2019) - SP

Grimm’s analysis:

Like in a standard fantasy draft, my strategy in the first round was to get the best player available. It seemed like every time I started to let myself believe a guy would get to me -- Alex Rodriguez, Sammy Sosa, Mike Piazza -- they went off the board just as quickly; I'd actually had my heart set on Piazza's bananas 1997 season, a clear outlier at the catcher position (I know I said BPA, but come on), before Jesse took him the pick prior to mine. Fortunately I'd identified Gerrit Cole's 2019 season as one that was elite in a smattering of advanced metrics, including the highest-qualifying K% and K-BB% and a top-15 batting average against. I'm gambling that those statistics matter more than things like ERA and wins -- not that 2019 Cole didn't have those, too -- and that Cole will challenge for the billing of top pitcher in our simulation.

1.16 Dwight Gooden (1985) - SP

Pianowski’s analysis:

I’m not the most experienced sim player in this room, so I can’t say for sure that Dwight Gooden 1985 is the proper pick here. But I liked the idea of landing No. 16 in slot 16, and I like the idea of keeping him forever young, with a 1.53 ERA and 0.97 WHIP at age 20. Anything seemed possible. Anything seemed within reach. (One could argue I didn’t even pick the right Gooden season, because his FIP and K/9 were much better as a rookie. Either way, I have an ace I can send out against anyone.)

1.17 Mike Trout (2018) - OF

Daugherty’s analysis:

I felt like I had a slightly better grip on the hitting landscape than pitching, so I went hitter. It was hard for this Cardinals fan to pass on an Albert Pujols season, but I decided before the draft I would allow OPS+ to be my lodestar for hitters, and Bryce Harper’s 2015 and Trout’s 2018 were tied for the best left. I had no real viable method for tiebreaking, but this being my first go-round with WhatIf Sports I … sort of understand the rules? I am going mostly by rate stats, but wasn’t positive how much stock I should be putting into straight up fantasy stats. With no other methods presenting themselves, I let Trout’s 24 2018 steals be the tiebreaker. This makes sense, maybe.

1.18 Jacob deGrom (2018) - SP

Short’s analysis:

I had my hopes pinned on Gooden slipping to me, so I turned to another Met once he fell off the board. Yes, it’s well-documented that I’m a Mets fan, but I promise this is purely coincidental. The fact is that deGrom’s 2018 is one of the best by a pitcher in recent memory. In addition to the minuscule 1.70 ERA, he fanned 269 batters with just 46 walks in 217 innings. He also had a 1.98 FIP, so the advanced metrics back up whatever randomness might have been at play. The only thing that hurt him from a fantasy perspective that year was a lack of run support. That shouldn’t be a problem in this league. Injuries aren’t going to be a concern here either, so I’m confident he’ll be one of the best pitchers in this simulation.

1.19 Justin Verlander (2019) - SP

Shovein’s analysis:

My plan coming into this draft was to hammer offense early on -- likely six or seven of my first eight picks. In order to make that work though, I needed an ace to front my starting rotation. When running my numbers (and adjusting for the run-scoring environment of the league in each of those seasons), Pedro Martinez (2000) and Randy Johnson (1999 or 2001) stood out above the rest. After those two, there was a small tier of Justin Verlander (2019), Jacob deGrom (2018), Clayton Kershaw (2014 of 2015) and Gerrit Cole (2019) from which I hoped one would fall to me at pick 19. Pedro was the first starting pitcher off the board at pick five, with Kershaw (9th), Johnson (13th), Cole (15th), Dwight Gooden (16th) and deGrom (18th) to follow. Had two starters from that tier been on the board for me, I would have gambled that Ryan Boyer wouldn't double up on starting pitchers at the turn, and I would have taken Vladimir Guerrero (2002) instead. Still, I was more than happy to take Verlander in that spot. Even in the year of the happy fun ball, with home runs flying out of major league ballparks at a record pace, JV managed to post a scintillating 2.58 ERA, 0.80 WHIP, 300/42 K/BB ratio and .171 batting average against. Not only did he have the best season of any pitcher in the American League -- Verlander delivered one of the best pitching seasons of the entire fantasy era during his age-36 season.

1.20 Vladimir Guerrero (2002) - OF

Boyer’s analysis:

Picking at the tail-end of the first round in a 20-team league isn't ideal even when you're drafting all-time great seasons. I felt I had no choice but to go with one hitter and one pitcher. Going hitter-hitter would have meant waiting 60 picks before I nabbed my first pitcher, which obviously would have been less than ideal. All things considered, I was happy to land Vlad Sr. and "The Rocket." I narrowed my hitter choice down to Vlad and Mookie Betts, who wound up going a couple picks later to D.J. Ultimately, I opted for Guerrero over Betts because he had a fairly significant edge both in the home run and stolen base departments. Clemens was really the only pitcher I considered; it was just a matter of which season to choose. I settled on 1997 over 1990 and 1988 because of the strikeouts, although I don't think I could've gone wrong with any of them.