This is not a pretty tale. It is full of ugliness and disappointment. You may want to stop reading now. I'm going to tell you a tale that will make your stomach churn. You may wake up screaming in the night after having read this. If you wish to stop reading now, I understand. In fact, I encourage it. Here's a link to pictures of puppies. I hope it makes you feel better.
The Cubs have not drafted well in their history. By at least one measure, they're the worst-drafting team in the history of the draft. Even when they do draft well, those players are often dealt to other teams for less than they ended up being worth. That record of woe is only slightly mitigated by a few steals like dealing Bobby Hill off to Pittsburgh for Aramis Ramirez.
In fact, by my count, in 50 years of the draft, the Cubs have only produced three players taken in the first round who had careers with the Cubs valued at over 5.0 WAR by Baseball-Reference: Shawon Dunston, Kerry Wood and Mark Prior. And even all three of those could be considered disappointments in one way or the other.
Now things aren't quite so bleak as that. There were some quality players taken in the first round who were traded for other quality players (Joe Carter for Rick Sutcliffe, Andrew Cashner for Anthony Rizzo) and of course the first round isn't the entire draft. The Cubs took one of the greatest players to ever play the game in the 2nd round one year. There are other successes in even later rounds. But overall, that record is pretty terrible.
If you want to know why the Cubs have not made the World Series since 1945, here's where you should start looking.
I'm dividing up the history of the Cubs into five groups: The Wrigley family years (1965 to 1981), the Dallas Green years (1982 to 1987), the Jim Frey/Larry Himes years (1988 to 1994), the Ed Lynch/Andy MacPhail years (1995 to 2002) and the Jim Hendry years (2003 to 2011).
Also, the Cubs gets zero credit for a player they drafted but did not sign. Too bad. There were some good ones.
The Wrigley Years (1965 to 1981)
Overview: One day I'm going to write the story of baseball in the sixties and seventies in terms of modernity. Those organizations that adopted modern, professional organizational structures and took a more analytic approach to the game thrived, like the Dodgers, Pirates, Cardinals and Orioles. (It's not an accident that Branch Rickey was associated with three of those teams, even if he was dead by 1965.) And then there are those teams like the Cubs, Giants and Red Sox that just kept doing things the same way they'd always been doing them, who struggled. Yes, occasionally those teams got lucky and managed to contend, but they had no way of maintaining excellence over the long haul. The Yankees were another team that continued in the old ways and they declined badly in the early 1970s. But they were saved by the advent of free agency and a huge purse.
P.K. Wrigley only had one job requirement for his scouts: He had to think you needed a job. Being able to scout wasn't important. Sure, some of the guys Wrigley hired really could scout, but that was besides the point.
It's hard to evaluate a draft in this time period because there was more than one every year. The Cubs' most famous pick in this time period, Burt Hooton, was the second pick of the June secondary draft in 1971. But most of the action took place in the regular June draft.
Grade: D. If I was just judging by the first round, this would be a shutout. The first Cubs first round draft pick (and we're not counting Hooton here) to have a major league career other than a cup of coffee was Roger Metzger, and he played one game for the Cubs. The only Cubs first round pick in the Wrigley era to produce a positive WAR in Chicago was Randy Martz. Seriously. That's the best first round pick. In 1981 when the Wrigleys were on their way out, the Cubs handed the GM reins to Herman Franks and he took Joe Carter, who had a nice career (and did bring great value back in trade).
The era only doesn't get an F because the Cubs grabbed some pretty talented pitchers in the later rounds. The first ever Cubs draft pick in 1965, Rick James, played three games in the majors. But their fourth-round pick, Ken Holtzman, easily returned first-round value. The Cubs would build a pitching rotation in the seventies out of Rick Reuschel (3th round, 1970), Dennis Lamp (third round, 1971), Ray Burris (17th round, 1972) and Mike Krukow (eighth round, 1973) Add in 1975 second-round pick Lee Smith and 1980 ninth-round pick Craig Lefferts and you've got a decent bullpen.
Best Pick: Reuschel, and it's not even close. Only two players drafted by the Cubs in history have had a greater career WAR value than Reuschel, one of the most underrated ballplayers in history. Of those that are better than Reuschel, one's going to the Hall of Fame and the other one might, although some ethical issues are currently standing in his way.
Best Draft: The Cubs got only Reuschel in the 1970 draft, but that's more than they got in any other draft. In 1969 the Cubs grabbed three players who had significant careers, Metzger, Larry Gura and Bill North. Of course none of them had those careers for the Cubs. So I'll say 1970 by default.
Worst Draft: So many to choose from, but I'll say 1967. With the second pick in the draft, the Cubs passed on Jon Matlack, John Mayberry, Ted Simmons and Bobby Grich to take Terry Hughes, who played 54 games in the majors and one with the Cubs. The rest of their draft produced a grand total of seven major league games.
The Dallas Green Era (1982 to 1987)
Overview: Cubs fans think this is the golden era of Cubs drafts, and they'd be right, although they weren't quite as good as we'd like to remember. Green fired pretty much everyone who had worked for the Cubs under the Wrigleys and replaced them with experienced baseball people, mostly from the Phillies. In this era, the Cubs built the team that won the 1989 NL East title through the draft.
The first pick that the Green team made was also the only No. 1 pick in the draft the Cubs ever had: Shawon Dunston. Sure, the Cubs would have been better off taking Dwight Gooden, but you can make a strong argument Dunston was the 2nd best player to come out of the first round of that draft.
But it was in 1984 that the Cubs struck gold, taking Greg Maddux in the second round and Jamie Moyer in the fifth. Again, those two would go on to produce most of their value for teams other than the Cubs, but at least both played for the Cubs for several seasons before moving on. (Of course, Moyer wouldn't get good until after he turned 33) The Cubs 1985 1st round pick was the only time they drafted someone in the first round with a career WAR over 28, Rafael Palmeiro. The Cubs followed that up with grabbing Mark Grace in the 24th round. That draft would likely have been perfect had only ninth-round pick Kevin Tapani had signed. At least Tapani later had a reasonably productive career with the Cubs anyway.
The 1986 draft produced a pair of catchers, Joe Girardi (fifth round) and Rick Wilkins (23rd round). The 1987 draft featured two mainstays of the 1990s Cubs rotation, Mike Harkey (first round) and Frank Castillo (sixth).
Best Pick: You could either say Greg Maddux, a Hall of Famer in the second round, or nabbing Mark Grace in the 24th, if you want to give extra points for being a late round pick.
Best Draft: Maddux and Moyer in 1984 edge Palmeiro and Grace in 1985, if only because a team has room for more than one starting pitcher but the Cubs didn't have room for two first basemen.
Worst Draft: Rich Amaral was the best player signed out of the 1983 draft. That should answer your question.
The Jim Frey/Larry Himes Years (1988 to 1994)
Overview: Frey and Himes don't have any connection to each other than the fact that they were both really, really terrible at their jobs. Twenty-five years later, Cub fans still mention Ty Griffin and Earl Cunningham every year the draft rolls around. If Cubs fans don't trust the draft, these years are the reason why.
Frey's front office was so terrible that the the 1988 through 1990 drafts did not produce a single player who had a positive career WAR. The longest career of anyone taken in those drafts was Kevin Roberson, whom I barely remember as a crappy utility infielder in the 1990s. Which shows you how forgettable Roberson was because he was actually an outfielder.
It's ironic that in Frey's final draft, 1991, he actually had a pretty good draft. First round pick Doug Glanville had a nice career, although Frey gets a major deduction because the very next player taken in 1991 was Manny Ramirez. But adding to Glanville, in the third round the Cubs picked Terry Adams and in the eighth they collected Steve Trachsel. Like Tapani in 1985, the Cubs took Jon Lieber in 1991 and failed to sign him, although Lieber would go on to have a solid Cubs career anyway.
Larry Himes gets a little slack because most of his picks were lower than the ones Frey botched, but Himes was 0 for 3 in drafts rather than Frey's 1 for 4. The best thing you can say about Larry Himes's drafts is that 20 years later, there are still two active major leaguers that he drafted and signed. If you had told me that in 1994, I would have been very impressed. If you would have told me they were Jose Molina and Kyle Farnsworth, I would have been a lot less impressed.
Grade: F. What else could you give them?
Best pick: Gotta go with Trachsel in the eighth round in 1991.
Best draft: Gotta got with Trachsel in 1991 again, along with Glanville and Adams.
Worst draft: So many to choose from. It would be funny to say 1991 also, because three of the next four picks after Glanville were Manny Ramirez, Cliff Floyd and Shawn Green. But I'll go with the infamous 1988 draft and the Ty Griffin selection.
The Ed Lynch/Andy MacPhail Years (1995-2002)
Overview: Lynch was MacPhail's man in the GM chair, so I feel comfortable lumping them together as one, even if MacPhail probably didn't take an active role in personnel matters throughout most of Ed Lynch's tenure as GM.
The Ed Lynch drafts got off to a roaring start in 1995 when he selected Kerry Wood with the fourth pick in the draft. With only a few years left in the century, the Cubs finally entered the 20th century under Lynch and MacPhail. Sure, it was too bad that other teams were entering the 21st Century around the same time, but baby steps, people.
Under Lynch, the Cubs started to actually draft players in the first round who became productive major leaguers. In three of Lynch's first four drafts, he managed to pick Wood, Jon Garland and Corey Patterson. We tend to remember Patterson as a bust, but he's more accurately termed a disappointment. In reality, Patterson played 1230 games in the majors and a career WAR of 9.6.
Andy MacPhail's draft philosophy, and by extension Ed Lynch's, was to draft as many pitchers as possible. That's certainly a high-risk strategy as pitchers suffer far more injuries than hitters, but the idea was that you could always trade away a pitcher to fill in other holes. And Lynch certainly did that. Besides the infamous Jon Garland for Matt Karchner deal, Lynch traded away a soft-tossing right-hander taken in the 29th round of the 1996 draft for Rick Aguilera. Of course, Kyle Lohse is still going strong.
When MacPhail took over the GM role after the 2000 draft, not much changed.
Grade: It's hard to grade this period because there were some real highs and some huge mistakes. And you can't blame the draft strategy for what happened to Mark Prior. So I'll average everything out and give them a C.
Best Pick: Take your pick between Kerry Wood, the fourth pick in 1995 and Mark Prior, the second pick in 2001.
Worst Pick: In 1999, Ed Lynch selected Ben Christensen with the 26th pick in the first round. If you don't know that story, look it up. This article is long enough as it is. But beyond all that, Christensen never pitched above Double-A.
Best Draft: For just the sheer number of players that became productive major leaguers, you can argue that MacPhail's first draft in 2001 was the best draft in Cubs history so far. Beyond Prior, the Cubs selected Ryan Theriot in the third round, Ricky Nolasco in the fourth (another traded away pitcher) and Geovany Soto in the 11th. Second-rounder Andy Sisco, fifth-rounder Brendan Harris and seventh-rounder Sergio Mitre all had major-league careers that lasted longer than a cup of coffee.
Worst Draft: In my mind, MacPhail's other draft, 2002, is the worst draft in Cubs history. It was in 2002 that his philosophy of putting all his eggs in the pitching basket really blew up on him. Despite having four (!!) first-round picks, two second-round picks and two third-round picks, the Cubs got ZERO major leaguers out of those eight picks. (OK, Billy Petrick had 9⅔ innings in the majors.) The Cubs also had two fourth-round picks and got Rich Hill out of that. By far the best player taken by the Cubs in the 2002 draft was a catcher in the 38th round: Randy Wells. I don't feel like giving them much credit for that one, although he was a credit to the Cubs improved player development system.
The Jim Hendry Years (2003 to 2011)
Overview: The final story of the Jim Hendry drafts has yet to be written, of course. He took a more balanced approach to the draft than MacPhail did, although his first pick in 2003, outfielder Ryan Harvey, was just as much of a bust as all the 2002 pitchers turned out to be.
Throughout much of Hendry's tenure, the Cubs were operating under financial restrictions connected to the pending sale of the team. Bud Selig was trying to get teams to agree to voluntary "slots," which all the smart teams simply ignored because Selig had no power to enforce them. Except in the case of the Cubs, of course, where Selig could throw roadblocks into Sam Zell's complicated sale plans if the Cubs made the commissioner angry. The Cubs also lost a lot of picks because of free agent signings. (Why not? There were no restrictions on money spent on major league players.)
This lead to some creative thinking on Hendry's part, such as the 2006 draft when the Cubs didn't have a 2nd through 4th round pick. Hendry took the underslot Tyler Colvin in the first round and came back with Jeff Samardzija in the 5th.
Grade: Incomplete. So far, he's looking at a B- probably. He could still pull out an A.
Best Pick: It's not Samardzija, although that was a really good pick. Hendry's best pick (so far) is 2007 supplemental first round pick Josh Donaldson . He really should have convinced Billy Beane to take someone else for Rich Harden.
Best Draft: Josh Vitters has certainly been a disappointment as the third pick of the 2007 draft, but it's still possible that he turns things around and becomes a productive player. But 2007 still takes the choice for best draft with Donaldson, Darwin Barney in the fourth round, and James Russell in the 14th. But it does look like 2011 will end up being the best when it's all over
Worst Draft: No one has made the majors from the 2010 draft and the first four picks, Hayden Simpson, Reggie Golden, Micah Gibbs and Hunter Ackerman are already out of the system. But Matt Szczur, Eric Jokisch, Dallas Beeler and others still have a chance to salvage the class.
The worst has to go to the 2005 draft. In what was the most loaded and talented draft of the past decade, the Cubs didn't get a single player out of it. Mark Pawelek only managed to throw two innings above Boise, for cripes sake. Jacoby Ellsbury, Matt Garza and Clay Buchholz, among others, sat on the board when the Cubs selected him.
Donnie Veal was the Cubs second-round pick and the Cubs left him unprotected in the Rule 5 draft a few years later He's managed to have some kind of career as a LOOGY for the White Sox the past couple seasons. If not for that, the production of the 2005 draft for the Cubs would consist of the two at-bats the Diamondbacks got out of Trevor Graham. And it's not like they were able to trade any of these busts, either
The Theo Epstein/Jed Hoyer Years (2012 to present)
Overview: This story has yet to be written.