A look back at two decades of what could have been in Cardinals drafts

As a way of demonstrating that I indeed passed the 10th grade, I will begin today's post with an excerpt from Robert Frost's omnipresent poem "The Road Not Taken."

"Two roads diverged in a wood, and I--

I took the one less traveled by,

And that has made all the difference."

Because it's a poem that everybody read in school (I'll be sure to work in some hot "The Lottery" takes into future posts), it has been analyzed and theorized into oblivion. The most common interpretation (one which evidently Frost did not share, but when you become the ultimate populist poet, you lose some say in the matter) is something along the lines of "it shows that you should go your own way."

But sometimes, the road somebody takes works out poorly. Sometimes it's a dead end. Sometimes it is filled with potholes. Relatively speaking, the Cardinals have taken some optimal roads in the last twenty years. The club's consistent success is a testament to that.

This does not mean, however, that the Cardinals have perfect information when they draft. Like any other team, they are at the mercy of imperfect and incomplete scouting reports, amateur statistics, and, of course, luck. And while the Cardinals have made some excellent selections during the Walt Jocketty and John Mozeliak eras, it is easy to wonder about the roads not taken.

Listed below are the Jocketty/Mozeliak first rounders. I omitted players from 2013 onward because it is far too early to evaluate the picks: only Marco Gonzales has played in the Majors among them. Additionally, I listed the player drafted between the Cardinals' actual pick and their next pick who has been the most productive MLB player--it felt unfair to indict the Cardinals for not, say, drafting Anthony Rizzo in the first round when the rest of baseball did not deem him worthy of higher than the 6th round pick the Red Sox used on him in 2007.

Finally listed is how many players drafted after the Cardinals pick and before the next Cardinals pick were/have been more productive MLB players by career Wins Above Replacement. For players with negative career WAR, I only listed players who made the majors as "better", as declaring guys who never made the show as "better" would put people such as myself as better than actual people quality of playing in Major League Baseball. Similarly, players with negative WAR drafted after Cardinals draftees who did not make the majors are listed as "better."

I suspect that your reaction to this table is a reflection on your worldview. The penultimate column is for pessimists; the far right column is for optimists.

On one hand, the Cardinals could have duplicated the best middle infield of the 21st century, Chase Utley and Jimmy Rollins of the Philadelphia Phillies, for Shaun Boyd and Braden Looper. Trade Justin Pope for David Wright, assume that the Cardinals can still draft Albert Pujols, and this is, without exaggeration, the best infield in the history of baseball.

Had the Cardinals drafted Adam Wainwright instead of trading for him, they could have kept 2004 J.D. Drew (assuming briefly he wasn't replaced with CC Sabathia) and his 8.3 WAR. This could put the 2004 Cardinals suddenly at around an estimated 111 wins, tied for the 4th-most in history.

Josh Donaldson and Brett Lawrie were famously traded for each other before the 2015 season, but the Cardinals could have had both instead of two-thirds of the pieces they dealt for two (albeit, awesome) months of Matt Holliday in 2009. They could have had Noah Syndergaard, one of the most electric young pitchers in baseball, instead of the guy they traded for Edward Mujica.

And while that season of Jason Heyward was fun, the Cardinals could have instead drafted Andrelton Simmons, arguably the best defensive shortstop in baseball since Ozzie Smith, rather than one of the pieces used to acquire Heyward. Oh, and instead of the other part of the Heyward trade, the Cardinals could have had Mike Trout.

Yes, it's too early for a drink.

But every team in baseball has had these misses. And while the Cardinals have missed out on some superstars, they have mostly succeeded in securing solid MLB-level talent. While Mike Trout would have been a certain upgrade over Shelby Miller, the Cardinals still got a Major League starting pitcher: two picks before Trout (you may have, once or twice, heard that the pick before Trout was Randal Grichuk), the Chicago White Sox drafted Jared Mitchell, a slightly less esteemed center fielder.

Of their 32 first round picks in this time, 22 were drafted out of 4-year colleges and universities. Their two highest picks of the last 20 years have been #3 overall Braden Looper, a 21 year-old 1st team All-American who played for Team USA in the 1996 Summer Olympics, and #5 overall J.D. Drew, 22, a college baseball superstar at Florida State who had played for the St. Paul Saints of the independent Northern League in the previous season. These were relatively safe picks in terms of on-field production (Drew's signability was a totally different, unrelated story).

And in later drafts, such as with Michael Wacha or the next year with Marco Gonzales, the Cardinals continued to operate under a fairly conservative model of drafting: yes, take some calculated gambles, but pick these points wisely. It's a delicate balance, and it leads to inevitable frustrations when the Cardinals, say, draft Chris Lambert 19th overall and don't find a use for him until he was sent to the Detroit TIgers as a Player To Be Named Later in the deal for Mike Maroth, whom I had admittedly forgotten was a Cardinal until circumstance brought me to Lambert's Baseball Reference page.

But it would be nearly impossible to argue that the system does not work. And when the Cardinals can draft guys like Matt Carpenter or Trevor Rosenthal (not to mention Albert Pujols) in later rounds, picking safe players to solidify rosters in the first round is not a bad strategy. Only time will tell if the latest crop of Delvin Perez, Dylan Carson, and Dakota Hudson fit the recent mold of solid MLB players, or perhaps reach the heights of what could have been for the Cardinals.