General Managers and scouting directors have a tough job. Every year they have to sort through thousands of 18- to 22-year-olds from all over the country and decide which ones will be great major leaguers in three to seven years or so. I don't blame them that they get it wrong so often. No team makes the right pick every time and most only make the right selection once a decade or so. Hindsight is 20/20. so they say.
But what if the Cubs had perfect hindsight? What if they could go back and change all of their first round pick this century? I went through the all the Cubs first-round draft picks with perfect hindsight and re-made all the picks for them. If the Cubs had let me make all of these picks today, they'd win the World Series.
And before you go through all these picks and say "Wow, do the Cubs make a lot better selections under Theo Epstein than they did under Jim Hendry," that may be true, but those picks are also getting a lot more hindsight scouting. The Schwarber pick looks great now, but it may look terrible in five years, for example.
2014. The Cubs selected C Kyle Schwarber. It's way too early to change the Cubs pick here. While there are still big defensive questions about Schwarber, he's currently one of the hitting prospects in the minors. Brandon Finnegan has had the best major league career so far from the 2014 draftees, but the Cubs wouldn't have needed a shutdown reliever last fall anyway. The Cubs still select C Kyle Schwarber (Indiana U.)
2013. The Cubs selected 3B Kris Bryant. Bryant already has the highest career WAR of anyone taken in the 2013 draft. With the benefit of hindsight, the Astros make Bryant the first pick in the draft. The Cubs still select 3B Kris Bryant (U. of San Diego)
2012. The Cubs selected OF Albert Almora. Almora is still in Double-A, which is not unusual for a player selected out of high school three years ago. Almora has shown the skills to be a top defensive center fielder in the majors, but he's struggled at times with the bat in Tennessee. Pitchers Michael Wacha and Alex Wood have been the stars of this draft so far, but the Cubs would probably go in a different direction. The Cubs select SS Addison Russell (Pace HS, FL). That worked out anyway.
2011. The Cubs selected SS Javier Baez. The final first round pick under GM Jim Hendry, Baez has shown a lot of promise and has been frustrating all at the same time. The Cubs probably aren't really regretting this pick yet, but with hindsight and a different GM, they may go in a different direction. The player with the highest career WAR out of this draft is Jose Fernandez, but since he's coming off Tommy John surgery, the Cubs might go in a safer directions. The Cubs select RHP Sonny Gray (Vanderbilt). Ironically, the Cubs did select Gray out of high school in 2008, but failed to sign him.
2010. The Cubs selected RHP Hayden Simpson. We can all debate whether injuries and illness derailed Simpson's career or whether he was just an insane pick in the first place another time. With the benefit of hindsight, of course the Cubs don't pick Simpson. With our perfect hindsight picks, the Cubs infield is just about to get a lot more crowded. The Cubs select SS Andrelton Simmons (Western Oklahoma JC)
2009. The Cubs selected OF Brett Jackson. The Cubs are starting to pick farther back in the first round, which means it's harder to get upset at missed picks because everyone starts to miss picks late in the first round. At least the Cubs are one of the teams that aren't beating themselves up about passing on Mike Trout, who went six picks before Jackson. Ironically, the Cubs' second round pick DJ LeMahieu would have been a solid choice on this spot. But since our hindsight is perfect. . . .The Cubs select 1B Paul Goldschmidt (Texas State). And this board would have melted down as the Cubs pick someone projected to go in the seventh to 10th rounds.
2008. The Cubs selected RHP Andrew Cashner. Not a bad pick and one that got a lot better when Cashner was flipped for Anthony Rizzo. This turned out to be a weak draft aside from Buster Posey (taken long before the Cubs selected). Even the first pick in the draft, Tim Beckham, is close to a complete bust. There are a few players taken after Cashner who are having slightly better careers, but none of them were flipped for Anthony Rizzo, so . . .The Cubs select RHP Andrew Cashner (TCU)
2007. The Cubs selected 3B Josh Vitters. With the third pick in the draft, the Cubs certainly wish they had this one over again. The player they were planning to select if Vitters was taken one pick earlier by Kansas City, Jarrod Parker, hasn't been able to stay healthy. Once again though, the Cubs selection in the supplemental rounds, Josh Donaldson, would have been a great choice here. But assuming Donaldson would still be available in the supplemental rounds, . .The Cubs select RHP Madison Bumgarner (South Caldwell HS, NC)
2006. The Cubs selected OF Tyler Colvin. This is a tough one in hindsight, because the Cubs real first round pick this year was Jeff Samardzija, who was taken in the fifth round. Colvin was a budget pick designed to allow the Cubs to pick Samardzija, who would have been a good choice for this pick. But with hindsight, we know that Samardzija is not going to play in the NFL, which was why he lasted until the fifth round in the first place. The Cubs select RHP Jeff Samardzija (Notre Dame)
2005. The Cubs selected RHP Mark Pawelek. The 2005 draft is likely going to go down as the greatest draft of all time, and the Cubs got Mark Pawelek out of it. When Scott Boras comes to you wanting to make a pre-draft deal, you've got to know something is fishy. The Cubs could have done better throwing a dart at the list of the top 50 prospects, but since Jacoby Ellsbury was taken just two picks after Pawelek, let's make this easy. The Cubs select OF Jacoby Ellsbury (Oregon State)
2004. The Twins selected RHP Kyle Waldrop with the Cubs pick as compensation for LaTroy Hawkins. Only one of these two is still in baseball. I wonder what odds you could have gotten back then that it would be Hawkins?
2003. The Cubs selected OF Ryan Harvey. Huge power. Couldn't hit a breaking pitch. Making this worse, Nick Markakis went to the Orioles one pick later. It wasn't a great draft, but the Cubs should have done better than Harvey. The Cubs select OF Nick Markakis (Young Harris College, GA)
2002. The Cubs selected RHP Bobby Brownlie. Here's the downside of picking a guy who dropped because of injuries. Sometimes they never come back. Brownlie was considered to be the top talent in the 2002 draft in January of that year, but his stock slid after several poor performances and missed starts with arm problems. The Cubs gambled that he could bounce back to what he was his sophomore season at Rutgers. They lost. Four picks later, the Giants took Matt Cain. The Cubs select RHP Matt Cain (Houston HS, TN)
2001. The Cubs selected RHP Mark Prior. He should have been one of the all-time greats. Right now, Prior should be finishing up a Hall of Fame career. We all know it didn't happen and there's no point in rehashing it again. Whether it all would have happened without Dusty Baker, I couldn't tell you and neither can anyone else. The Cubs plan was to take Mark Teixeira had the Twins defied Prior's wishes and taken him with the first pick. That would have been a great choice, but I think there is one that was slightly better. The Cubs select 3B David Wright (Hickory HS, VA)