1. First Round = Golden Ticket
Baseball inaugurated the amateur draft during the 1964 winter meetings. It was initially billed as a way of leveling the playing field, stopping teams like the Yankees from establishing dynasties by outbidding their rivals for amateur talent. This was done with Major League Baseball's usual sense of timing -- the Yankees had won the American League pennant that year, but they were done, having in fact ceased spending on prospects several years before as ownership contracted expenses on the way to selling out. Had the moguls known, they hardly would have cared given that the main goal wasn't competitive balance but reining in costs by restricting talent's ability to negotiate to one party.
The draft was only partially successful at this, as the institution of a slotting system suggests, but over time it did cause clubs to improve at identifying talent. With the ability to cast a wide net removed, teams were forced to get their picks right if they wanted to keep talent coming to the major league team. A first-round pick in particular became an extremely valuable commodity. Prior to the first draft, it was speculated that only two out of 10 picks would make it to the majors. The first round would eventually mute such pessimistic assessments. For example, in each of the 10 drafts from 1999 to 2008 the vast majority of players selected with the first 30 picks reached the major leagues:
1999: 14 (top 10 6/10)
2000: 16 (5/10)
2001: 19 (7/10)
2002: 24 (8/10)
2003: 22 (7/10)
2004: 26 (8/10)
2005: 26 (9/10)
2006: 24 (9/10)
2007: 21 (9/10)
2008: 24 (9/10)
The four top-10 selections not to make it from 2005-2008? Rays pitcher Wade Townsend (eighth overall), Orioles infielder Billy Rowell (ninth), Rockies pitcher Casey Weathers, and Rays shortstop and first-overall pick Tim Beckham. Beckham, just 23 and playing at Triple-A Durham, may yet get a call to the big leagues.
Overall, just three first-overall picks prior to Beckham have failed to make it to the majors at all: Mets catcher Steve Chilcott (more about him below); Yankees left-hander Brien Taylor, who suffered a devastating arm injury in a fight; and Padres infielder-pitcher-scumbag Matt Bush.
2. Don't Overthink It I
When teams have missed in the first round it has often been because they let non-baseball factors cloud their reasoning. When the Padres spent 2004's first-overall pick on shortstop/convicted drunk driver Matt Bush, thereby letting Justin Verlander fall to the Tigers at No. 2, it wasn't because Padres' talent evaluators truly thought Bush, a local high school product, was the superior player, but because ownership didn't want to meet Verlander's bonus demands. The Pirates taking Bryan Bullington with the first-overall pick in 2002 was also made with savings in mind.
Possibly the most infamous first-round selection of all time was made not due to cost, but possibly out of racism -- either that or the Mets just missed. Coming off of their fourth straight 100-loss season, the Mets had the first-overall pick in the 1966 draft. An Arizona State University outfielder named Reginald Martinez Jackson was the consensus top talent in the draft, an estimate which time and distance have done nothing to change. On draft day, the Mets chose high school catcher Steve Chilcott instead.
As far as we can tell from the little playing he ultimately did in the Mets system, Chilcott was talented. Unfortunately, injuries intervened and he never made the majors. Heck, he hardly made it to Triple-A. In the book he dictated to Mike Lupica, Jackson quotes ASU manager Bobby Winkles as telling him that though he had hit a school-record 15 home runs, the Mets would not be drafting him. "They're concerned you have a white girlfriend."
Years later, people associated with the Mets front office said that Casey Stengel had scouted Chilcott and turned in a positive report. So that was the real reason, not racism, but the word of a 76-year-old ex-manager, no longer full time with the organization. Right.
3. Don't Overthink It II
The Atlanta Braves, then a franchise lost at the bottom of the standings, had the first-overall pick in 1990. The consensus top talent that year was Texas high-school right-hander Todd Van Poppel. The Braves seemed willing to take him, but Van Poppel let it be known that that he had no interest in going to Atlanta. The Braves shed a bitter tear or two and drafted Chipper Jones instead. Van Poppel dropped to the A's at No. 14 and went on to a highly disappointing career.
4. Don't Overthink It III
A few players have been selected in the first round of the draft, declined to sign, and then returned in stronger position in a subsequent draft. Catcher Jason Varitek was the 21st-overall pick in the 1993 draft, but wasn't interested in taking the Twins' money and headed back to Georgia Tech for his senior year. The Mariners made him the 14th-overall pick the following year.
Outfielder J.D. Drew was taken by the Phillies with the second-overall pick in 1997 but didn't want to play in Philadelphia. A dozen years earlier, the Phillies might have been able to sign Drew and then immediately trade him, but such a sequence was prohibited after Pete Incaviglia, the eighth-overall pick of the 1985 draft, refused to play for the Expos and was dealt to the Rangers. With the two clubs at an impasse, the Phillies went home empty-handed -- they would spend a 1998 compensatory pick on Eric Valent -- and Drew headed off to the independent Northern League. The Cardinals took Drew with the fifth-overall pick in 1998 and signed him about a month later.
A more recent, and more typical scenario involved Pirates right-hander Gerrit Cole. Cole was the 28th-overall pick in 2008's first round, but the then-high schooler turned down the Yankees to go to the University of California. Three years later, the Pirates made him the first overall pick in the 2011 draft. He should reach the majors sometime this year.
Delaying has notably backfired in a few cases, most famously with right-handed pitcher Matt Harrington. The California prep prospect was taken by the Rockies with the No. 7 pick in the first round of the 2000 draft. He declined to sign with them, turning down a $4 million bonus -- what pitcher would choose to go to Denver? The first round was a bit light on talent that year, and it's hard to say that the Rockies missed out on a whole lot by selecting Harrington; only two of the next eight picks made the majors. Chase Utley and Adam Wainwright lurked lower down in the round but clearly weren't considered top-10 talents. The Rockies took Jayson Nix with their 2001 compensatory pick.
Meanwhile, Harrington went off to St. Paul of the Northern League and pitched very poorly. Scouts weren't completely deterred however, and the Padres spent a second-round pick on him in 2001 and offered him $1.25 million. He said no. In 2002 he pitched in the independent Central League and Western League and was miserable in both, with diminished velocity. The Rays drafted him in the 13th round of the 2002 draft, but didn't sign. By 2003 he was 21 and was still pitching like an independent-league mediocrity. The Reds drafted him in the 24th round, taking a flier with the 711th-overall pick. You guessed it. He didn't sign. Finally, the Yankees tried to deflect rumors that they were totally without a sense of humor by selecting Harrington with their 2004 36th-round pick and offered two tins of sardines as a bonus. That last might not be true, but it should be. In any case, the 1089th pick of the draft never put on pinstripes.
5. Is This Trip Really Necessary?
Since the advent of free agency, teams have risked the forfeiture of their first-round draft picks for signing a player. This can make sense in some cases: As valuable as a first-rounder has proven to be, the chances of that player developing into an MVP or Cy Young award winner are very slight. Thus, if a team is in the increasingly rare position of signing a mature major leaguer at the top of his game, the risk is actually very low. Every now and again a team will come out looking bad in the exchange -- for example, the Angels took their compensatory pick from the Yankees for losing designated hitter Don Baylor and turned it into Wally Joyner -- but for the most part, if the veteran plays well the signing team will likely have come out ahead.
Probably the worst exchange of this kind came in 1982, when the Montreal Expo signed Type-B free agent Tim Blackwell, a 29-year-old reserve catcher with career rates of .230/.332/.306 to that point. Though they were in need of a backup catcher, their starter was Gary Carter, so Blackwell was purely a luxury item. The Cubs didn't do anything special with the pick they received from the Expos, but we can't know who Montreal would have taken. Whoever he was, had he made the majors at all he would almost certainly have provided more value than Blackwell, who received all of 61 plate appearances from the Expos over the next two seasons.
6. If You're Young and a Catcher, First Baseman, or Second Baseman, Your High School or College Coach has Probably Screwed You
The draft puts a premium on pitchers (for obvious reasons), as well as shortstops and center fielders. If a player can't play short as a professional, he's still probably athletic enough to move to another position, and if a center fielder proves to lack range but still has a bat, he can shift to one of the outfield corners. Catchers, first basemen, and second basemen don't have that kind of versatility -- if a catcher can hit but can't catch, he can perhaps move to first base or an outfield corner, but then he's under immense pressure to hit at the highest level. First basemen have the highest offensive burden of any position, and if their bat is a bit short for the position, they probably lack the athleticism to move elsewhere. Finally, a second baseman who can't play second but hits like a middle infielder isn't going to make the majors, since a utility infielder has to be able to play short.
As a result, these three positions tend to be underrepresented in the first round, where the big money is. From 1965 to present, only 111 catchers have been taken during the first round proper (that is, not including the supplemental segment). This may seem like a large number, but compared to players selected at other positions it's rather small. The number of catchers selected first overall is just five -- the aforementioned Steve Chilcott was the first, followed by Mike Ivie in 1970, Danny Goodwin (once in 1971, once in 1975), and Joe Mauer in 2001.
Catchers, though, have been popular compared to second basemen. In over 40 years of drafting, clubs have picked a second baseman in the first round just 15 times and never first overall. Most recently, Cardinals prospect Kolten Wong was selected with the 22nd-overall pick of the 2011 draft. Critics worried that they had made a poor gamble, but so far Wong has made the Cards look good.
First basemen fall between the two extremes of catcher and second base. Seventy first basemen have been picked in the first round (most recently Angels minor-league slugger Chris Cron, taken 17th overall in 2011), but only three have been drafted first overall: Ron Blomberg by the Yankees in 1967, Harold Baines by the White Sox in 1977 (he would play right field as a major leaguer), and Adrian Gonzalez by the Marlins in 2000.