Major League Baseball is conducting its 50th first-year player draft this week, and we thought it would be a golden opportunity to take a 50-year retrospective on the baseball draft as part of our general preview coverage of this year’s proceedings.

Naturally, we’ve enlisted our resident draft historian, Allan Simpson, to take a look back at some of the highlights—and lowlights—of the draft through the years and shed some of his own perspective on how the draft has evolved, and the impact it has had on the game.

Allan has done so by randomly selecting a cross-section of 50 signature moments, developments, topics or trends in draft history, beginning with the first draft in 1965. He has focused on some of the best and worst picks ever made, drafts that changed the fortunes of franchises—positively or negatively—for years to come, the success and failure rates of select draft picks, changing demographics and the impact escalating signing bonuses have had on the process. He has also slipped in a few draft trivia-related items that even some of the more-knowledgeable observers of the draft may never have been aware of.

We’ll run our 50/50 special over a two-day period, with the first 25 items scheduled for today and the other 25 on Tuesday—in plenty of time to digest a little draft history before the 50th draft kicks off with a bang on Thursday.

Ten Most Iconic Moments
There have been plenty of attention-getting moments or developments over the near-50-year life of the baseball draft, but here, in a nutshell, are 10 that stand out most.

1. Bo Knows Baseball
The Kansas City Royals scored a major coup for baseball with their bold, calculated move in 1986 to snatch away Bo Jackson, the reigning Heisman Trophy winner and No. 1 overall pick in that year’s football draft, right from under the nose of the NFL. With his exceptional power/speed package, Jackson may be the single greatest raw talent to play Major League Baseball in the draft era, and his impact on the game—even in his brief, injury-riddled career—was substantial.

2. Twice the Hype
Few players in draft history have been as talented or generated more pre-draft hype than right-hander Stephen Strasburg (class of 2009) and catcher Bryce Harper (class of 2010)—and the Washington Nationals hit the jackpot by drafting both in consecutive years. Rarely has the baseball draft been so relevant in the mindset of the national conscience as it was with this pair, though a case can be made that Louisiana State right-hander Ben McDonald created his own draft magic in 1989, when he was every bit as much of a pre-determined no. 1 pick as Strasburg was 20 years later.

3. Sign of Things to Come
The New York Yankees sent shock waves through the industry in 1991, when they signed North Carolina prep left-hander Brien Taylor, the no. 1 overall pick that year, to a $1.55 million bonus—almost three times the existing record. The old mark of $575,000 was set in 1989 by John Olerud, a third-round pick of the Toronto Blue Jays, and matched earlier in 1991 by Mike Kelly, drafted second by the Atlanta Braves. Taylor’s contract, signed just hours before he was set to enroll at Louisburg (N.C.) Junior College, triggered an unprecedented wave of bonus escalation that would continue largely unabated over the better part of the next two decades. The Yankees got nothing for their investment in Taylor as his promising career careened downhill, topping out in Double-A, after he injured his shoulder in a fight.

4. Sacrificial Lamb
Texas schoolboy left-hander David Clyde fashioned one of the greatest careers in prep baseball annals, making him a near slam-dunk choice as the No. 1 pick in 1973. The Texas Rangers showed no hesitation in drafting him, and the move played right into the hands of opportunistic owner Bob Short, who saw in Clyde a windfall opportunity to give his ailing franchise a significant shot in the arm. Clyde was promoted directly to the Rangers rotation, and not only did he win his much-hyped debut, but the sideshow that accompanied it provided Short’s transplanted Rangers their first-ever sellout. Short’s short-sighted cash grab, however, came at a significant cost as an emotionally-scarred, ill-prepared Clyde went only 18-33 in his big-league career—hardly a performance worthy of his talent, and nothing like the careers enjoyed by future Hall of Famers Robin Yount and Dave Winfield, who were taken with the third- and fourth-overall picks that year.

5. Opportunistic Strike
If ever there was a case for a draft and its inherent powers to suppress bonus payments, the Loophole Free-Agent Fiasco of 1996 provided it. First-rounders Travis Lee (Twins), John Patterson (Expos), Matt White (Giants), and Bobby Seay (White Sox) all became free agents that year after successfully challenging a little-enforced rule in the Professional Baseball Agreement that required clubs to tender formal contract offers to their draft picks within 15 days of being selected. The snafu coincided with recently-minted expansion teams in Arizona and Tampa Bay, and those clubs saw the free agents as a windfall opportunity to add frontline talent not otherwise available to them. Between them, the Diamondbacks and Devil Rays signed all four, shelling out signing bonuses totaling roughly $30 million. White, a promising Pennsylvania high-school right-hander who was under consideration to be drafted first overall, signed the largest bonus of the four, a staggering $10.2 million, but was the only one of the quartet never to play in the big leagues.

6. Baseball’s Ultimate Human-Interest Story
Jim Abbott was born without a right hand, but never let his handicap stand in his way from assembling one of the most-inspirational careers of the draft era. After becoming the only baseball player to win the James E. Sullivan Award, symbolic of the nation’s best amateur athlete, to cap off a vintage college career at Michigan, Abbott was taken by the California Angels with the eighth pick in the 1988 draft, and only added to his growing aura by leading the U.S. to gold that fall at the Seoul Olympics. Understandably, the atmosphere in Anaheim was at a fever pitch the following spring when Abbott made his long-awaited pro debut as one of only 21 picks in draft history to play in a major-league game without first appearing in the minors. Abbott went on to pitch 11 years in the majors, and his 1993 no-hitter, while a member of the New York Yankees, may have been his only outing that usurped his emotion-charged debut.

7. Lightning Rod for Controversy
The baseball draft has had its share of noteworthy holdouts and controversial, contentious signings through the years, but few players struck a chord that reverberated throughout the game quite like outfielder J.D. Drew. His antics were not only felt over the course of two drafts, but led to a renaming of the very draft itself. As a talented, much-in-demand junior outfielder at Florida State in 1997, Drew was drafted second overall by the Phillies, but he and agent Scott Boras caused such furor and consternation in Philadelphia with a contentious negotiation that a deal between the parties was never struck. Rather than simply return to FSU for his senior year, Drew opted to forgo his remaining amateur status by signing on to play in the independent Northern League the next spring. But his overriding intent was not to prepare himself for the 1998 draft as much as it was to become a free agent, and he subsequently pleaded his case to an arbitrator that he was then a professional, and thus no longer subject to baseball’s “amateur” draft. Major League Baseball moved quickly and successfully to defend and defuse the unprecedented maneuver, and it was ascertained that Drew would still be subject to the newly-renamed “First-Year Player Draft” in 1998. Drew tore up the Northern League in his brief tenure and again dominated much of the pre-draft hype in his second go-around, but the Phillies, selecting first that year, steered well clear of him and Drew ended up going to the Cardinals with the fifth pick and signed shortly thereafter.

8. The Dilemma
Major-league teams have routinely agonized over selecting one talent vs. another throughout draft history, and the stakes are never higher than with the team in the often-unenviable position of drafting first. The 1966 draft has served as a constant reminder of the potential consequences involved. The New York Mets were in a quandary that year over whether to pick California high-school catcher Steve Chilcott or Arizona State outfielder Reggie Jackson with the no. 1 pick. They opted for Chilcott, and have never quite lived down that decision through the years as Chilcott failed to reach the majors in seven injury-plagued minor league seasons, while Jackson went on to enjoy a much-celebrated, Hall of Fame career—much of it spent in New York with the cross-town Yankees, where he was a constant reminder to the Mets of what could have been.

9. Finally, a Workable Solution
The baseball draft was instituted in 1965 as something of a last-resort measure after big-league officials felt they had exhausted all other potential avenues in trying to solve an age-old problem: containing escalating bonus payments to amateur players. For the better part of the next 25 years, the draft served its intended purpose of controlling bonuses (while also distributing talent equally among clubs), but with the game in a growth spurt and suddenly awash in cash in the late-80s and early-90s, clubs began spending more freely on high-school and college talent, and bonuses soon skyrocketed. From a first-round average of $176,008 in 1989, the norm grew to more than $2 million by 2001 and peaked at $2,653,375 in 2011. Try as it might, the commissioner’s office was almost powerless in its variety of efforts to scale back bonuses, and it became almost like history repeating itself, 50 years later, with the very foundation of the game under attack stemming from another potential crisis related to the payment of lofty signing bonuses. In the fall of 2011, though, a new Basic Agreement that targeted the draft and its inequities ushered in the most-sweeping changes to the draft since the very process was instituted 47 years earlier. Among the measures aimed at limiting bonuses in the future was the establishment of aggregate signing bonus pools, which set an upper limit on the amount that teams could spend on their draft picks in the first 10 rounds, and enforceable penalties—in the form of fines and forfeited draft picks—if a team failed to comply with the new standards and exceeded its assigned bonus limit.

10. Age of Enlightenment
The baseball draft may never be confused with the NFL and NBA drafts in terms of its popularity and rightful place on the American sporting landscape, but it has become exponentially more visible—and popular—over the last decade. That stems in large part from Major League Baseball’s decision to finally remove the shackles of secrecy and openly promote the draft as a meaningful event on the baseball calendar. For the better part of 20 years, MLB went to great lengths to protect its proprietary rights to basic draft content, to a point of temporarily withholding the public dissemination of information on its draft picks, especially as some of it might be used to advantage by agents and college coaches. In a nine-draft stretch from 1989-97, MLB even went so far as to withhold the releasing the names of drafted players (with the exception of the first round) for a week after the draft, and then only in alphabetical order by clubs. The round-by-round order was not made public for a period of months. But this author, back in his day as the editor-in-chief of Baseball America, long the media leader in meaningful draft coverage, openly defied Major League Baseball’s edict on secrecy, and challenged the commissioner’s office to make the entire draft list, round-by-round, available immediately—even threatening, on the eve of the 1998 draft, to piece together a minimum of the first 10 rounds through industry sources, and publishing it essentially in real time. When MLB officials got wind of BA’s intentions to circumvent their short-sighted blackout policy, the commissioner’s office quickly backed down from its long-standing, hands-off stance, and in a complete reversal of policy, it made all 1998 draft content (all 50 rounds) available immediately. Major League Baseball has since come full circle in its willingness and desire to openly promote its primary player-procurement process, with on-site television coverage as a primary medium, and the popularity of the baseball draft has soared in the process.

Other Signature Developments in Draft History

11. Rick Monday, Forever No. 1
Then a 19-year-old sophomore outfielder from College World Series champion Arizona State, Monday was taken first overall in the first draft in 1965 by the Kansas City Athletics. He was awarded a $100,000 signing bonus by A’s owner Charles O. Finley, exactly half the record pre-draft amount that Rick Reichardt received a year earlier from the Los Angeles Angels—a bonus considered so extravagant at the time that it was the trigger point for a draft system finally being instituted a year later. After Monday, who enjoyed a distinguished 16-year big-league career and remains in the game as a play-by-play broadcaster with the Los Angeles Dodgers, bonuses were so suppressed in a restrictive draft system that it would be 11 more years before another draft pick received a six-figure bonus.

12. Growing Impact on Hall of Fame
There have been 1,326 first-round picks (June, regular phase) since the inception of the draft. To date, seven have gone on to become Hall of Famers, although that number will certainly grow with time, especially as today’s active players complete their careers and the most-deserving ones serve out the mandatory five-year wait until their eligibility for the Hall kicks in. Of note, no player selected first overall has ever been elected to the Hall of Fame, though that will undoubtedly change soon, or once Ken Griffey Jr. (Class of 1987) and Chipper Jones (Class of 1990), who assembled Hall-of-Fame worthy careers, become eligible. The highest-drafted current Hall of Famer is Reggie Jackson, the second pick in 1966, while Robin Yount (Class of 1973) and Paul Molitor (Class of 1977) were both third-round picks of the Milwaukee Brewers. They were followed in quick order by Dave Winfield (Class of 1973) and Barry Larkin (Class of 1985), fourth overall picks in their respective draft classes. In all, 26 draft picks have gone on to become Hall of Famers, though that number will swell by three this summer when Greg Maddux and Tom Glavine, both second-rounders in 1984, and Frank Thomas (Class of 1989) are inducted. Thomas is the most recent draft pick to be selected. With the inclusion of Maddux and Glavine, the second round will have produced six Hall of Famers and the third round five. Technically, the lowest-round draft pick to reach the Hall of Fame is Ryne Sandberg, a 20th-rounder in 1978, but Bruce Sutter was a 21st-round pick of the Washington Senators in 1970 out of a Pennsylvania high school, although he didn’t sign at the time. After briefly attending college at Old Dominion but dropping out soon enough to be eligible for the 1971 draft, Sutter went undrafted and later signed with the Chicago Cubs as a free agent.

13. Footnotes in Draft History
Only 21 draft picks have played in a major-league game without first auditioning in the minor leagues. Just one, third baseman Bob Horner, who set the collegiate career home-run record at Arizona State in 1978 on his way to being picked first overall that year by the Atlanta Braves, completely justified his case for starting his career on top as he homered 23 times in 89 games after signing with the Braves and earned National League rookie-of-the-year honors in the process. Two more collegiate stars, Dave Roberts (Oregon) and Dave Winfield (Minnesota), also had representative debuts after being taken straight to the big leagues in consecutive drafts (1972-73) by the San Diego Padres. The phenomenon occurred 12 times in the 1970s, including all four instances where a team attempted to capitalize on the publicity value of a first-round pitcher making his professional debut in the big leagues, as was overtly the case with David Clyde (Rangers) in 1973, and Eddie Bane (Twins), Tim Conroy (A’s) and Mike Morgan (A’s) in 1978. A fourth 1978 draft pick, prep catcher Brian Milner, began his career in Toronto as an inducement to forego a promising college football career, and went an encouraging 4-for-9, but was never heard from again after being sent to the minors. Several more draft picks debuted in the big leagues because they were signed to rare major-league contracts—John Olerud (Blue Jays) in 1989, Darren Dreifort (Dodgers) in 1993, Ariel Prieto (A’s) in 1995, and Xavier Nady (Padres) in 2000, to name the most recent few. Others like Pete Incaviglia (Expos, later traded to the Rangers as a condition of his signing) in 1985, Jim Abbott (Angels) in 1988 and Mike Leake (Reds) in 2009 didn’t begin their professional careers until the following year, and had the obvious advantage of a full spring-training camp to better acclimate them to the pro game. The first three picks in the secondary phase of the 1971 draft—right-handers Pete Broberg and Burt Hooton, and third baseman Rob Ellis—all were taken directly to the big leagues. Right-hander Mike Adamson, meanwhile, holds the distinction of being the first drafted player to debut in the big leagues. An unsigned first-rounder of the Philadelphia Phillies in 1965, Adamson attended college at Southern California for two years before being taken by Baltimore with the initial selection in the June, 1967 secondary phase. Adamson’s stay was short-lived, and he never went on to win a big-league game in his professional career.

14. Draft for the Ages: Part I
Though the draft was still in its infancy in 1968, and baseball executives were still trying to figure out the nuances of piecing together a successful draft strategy, the Los Angeles Dodgers seemed to have all the answers that year. The mother lode of talent they assembled still stands the test of time as the greatest single draft ever. The Dodgers drafted three-fourths of an infield (first baseman Steve Garvey, second baseman Davey Lopes and third baseman Ron Cey) that, along with shortstop Bill Russell (a 1966 draft pick), remained intact for almost nine years, and led the team to three pennants in the 1970s with it all culminating in 1981, when the Dodgers won the World Series. Fifteen players were drafted by the Dodgers in 1968 that went on to play in the big leagues. Bobby Valentine and Bill Buckner were selected in the first two rounds, but the team also landed established future big-leaguers like Tom Paciorek in the fifth round, Joe Ferguson in the eighth, and Doyle Alexander in the ninth. As previously-drafted college players, Garvey (first round) and Cey (third) were subject to the secondary phase of the June draft that year, while Lopes was a product of the January secondary phase.

15. Inexact Science: Part I
The baseball draft stands apart from drafts in all other major professional team sports because it deals with unfinished products. As a result, there is often a significant degree of projection involved in establishing the future worth of a typical drafted player, especially raw high-school talent. The more projection involved, the greater the chance for a mistake being committed, and there have been some colossal gaffes in the first round through the years. Perhaps none has been as graphic as the Minnesota Twins selection of Wisconsin high-school outfielder Kevin Brandt with the 11th pick in 1979. Brandt was so overmatched that he was released by the Twins little more than a year later, after hitting a meager .155-1-9 in 47 Rookie-league games. His equivalent counterpart on the mound, righthander Mark Snyder, who was chosen 12th overall by the Cleveland Indians in 1982, never won a game in pro ball, going 0-5, 7.20 in 11 appearances, none above low Class A, though in fairness his career was ravaged by arm problems.

16. Better Late Than Never
Today’s draft is limited to 40 rounds, a reduction from the 50 rounds that were in place from 1998-2011. But from the outset of the draft in 1965 until 1997 (with the exception of 1992, when there were 50 rounds), teams could draft at will—and often did so beginning in 1987, when the draft was consolidated from four phases (two in January, two in June) to a single June phase. The New York Yankees took things to an extreme in 1996, when they drafted through a record 100 rounds—though they actually selected future big-leaguers Clay Condrey in the 94th round and Scott Seabol in the 88th. Condrey never signed with the Yankees and didn’t agree to a pro deal for another six years when he was signed by the San Diego Padres as a free agent out of McNeese State University, but went on to pitch six years in the big leagues. He stands as the latest draft pick to ever play in the big leagues. Righthander Travis Phelps, meanwhile, holds the distinction of being the lowest-round pick to reach the big leagues with the team that drafted and signed him. He was taken in the 89th round by the Tampa Bay Devil Rays out of Crowder (Mo.) JC in 1996 on his way to a three-year, big-league career, the first two with the Rays.

17. Best Draft I: 1985
With headliners like Barry Bonds, Barry Larkin, Rafael Palmeiro, Will Clark, and B.J. Surhoff, the star-quality talent that came out of the first round of the 1985 draft trumps any draft in history—though 2005, in time, could give it a run for its money. Led by that quintet, the cumulative WAR (Wins Above Replacement) value of the first round in 1985 is 495.7—easily better than the first round of any draft. The talent produced didn’t stop there, either, as Randy Johnson was taken in the second round and John Smoltz was a 23rd-round afterthought. And that doesn’t even begin to address the likes of Bobby Witt and Pete Incaviglia, the third and eighth overall picks that year, or Bo Jackson, an obvious first-round talent who lasted until the 20th round because of his football obligations at Auburn, and didn’t sign for another year. None of those three displayed the sustained success over their careers like some of the more-acclaimed first-rounders in the 1985 draft, but Incaviglia hit 48 home runs that year at Oklahoma State to set an NCAA record that may never be broken, while Witt and Jackson often showed flashes of brilliance—a testament to their still being the only players in draft history to score a perfect 80 on the Major League Scouting Bureau’s 20-to-80 grading scale. It was no coincidence that the star power that characterized the 1985 draft was almost all college players who had also factored prominently into the top 10 rounds of the 1982 draft, as high-school players, only to go unsigned. In the end, there is little disputing the 1985 draft’s lofty WAR ranking, but that measuring stick doesn’t differentiate whether a player signed, so the cumulative WAR score through Rounds 1-5 in 1982 (845.3) is actually higher than for 1985 (749.0). Bonds, Larkin, and Jackson were all unsigned second-rounders in 1982, which accounts for that round producing the highest WAR grade on record. Additionally, Clark and Johnson were unsigned fourth-rounders in 1982, which accounts for that round having the highest all-time WAR score.

18. Meager Investment
Third baseman Bob Jones, the 20th and last pick in the first round in 1966, has the distinction of receiving the smallest signing bonus of any first-rounder in draft history—a meager $9,000 investment by the Minnesota Twins. Predictably, Jones never played above Class A in four minor-league seasons. Shortstop David Espinosa, meanwhile, received no bonus at all upon signing with the Cincinnati Reds as the 23rd overall pick in 2000. He held out all summer trying to reach an accord with the Reds and finally agreed to a unique, incentive-laden deal that provided a significant payoff if, and when he reached the big leagues, but Espinosa never surfaced above Triple-A in a 10-year minor-league career.

19. Thanks, But No Thanks
Over the near-50-year life of the draft, six players have been selected in the first round (June, regular phase) who never went on to play professional baseball—not counting recent unsigned Blue Jays draft picks Tyler Beede (2011) and Phil Bickford (2013), and Padres pick Karsten Whitson (2010), who are still in college. Three of the six chose to pursue football careers, including Condredge Holloway (Expos, 1974), who played four years of baseball at Tennessee and in the process became the first African-American quarterback in Southeastern Conference history. Holloway later went on to a 13-year, Hall-of-Fame career as a quarterback in the Canadian Football League. Former Montreal Expos officials still maintain that Holloway chose playing in the SEC over a career in baseball because he made more money playing football in college than the Expos offered him as a signing bonus. In 1986, Greg McMurtry, a Massachusetts high-school product, opted to play football at Michigan rather than sign with the hometown Red Sox, and eventually went on to an NFL career as a wide receiver.

20. Coming of Age
From 1965-80, the first round of the draft (June, regular phase) was heavily populated by high-school players with 296 selections overall, compared to just 78 from the four-year college ranks and one from junior college. One player was picked who was not attending a school of any kind. In 1971, all 24 players drafted in the first round were from high school. Those numbers are skewed to a large degree, though, as many of the better college players from that era were subject only to the secondary phase—especially if they were re-drafts, though the rules that applied to previously-drafted players were frequently amended, and eventually almost all college players that had been drafted out of high school became the domain of the conventional June regular phase. In 1981, though, there was a sudden and dramatic shift in demographics with 17 of 26 first-round picks coming from college, and 34 of the first 50—double the previous record. The reverberations were felt throughout the draft as twice as many college players as high school players were selected that year, and a record-low 113 prep players signed overall. By 1985, the influence of college baseball on the draft had become so pronounced that 11 of the first 12 selections were from the college ranks, and most drafts since have been more heavily-weighted towards college talent.

21. Worst Draft I: 1975
The talent in the 1975 draft wasn’t necessarily the weakest ever, but the way it was distributed in the first round certainly was. Only 12 of 24 first-rounders that year played in the big leagues, but that included only one of the first five selections. And that player was none other than Danny Goodwin, who has distinction in draft history for becoming the only player selected twice with the first overall pick—in 1971, and again in 1975. Curiously, Goodwin was drafted as a catcher on both occasions—first out of an Illinois high school, later as a four-year starter out of Southern University—and yet never caught even one game in the big leagues in an undistinguished, seven-year big-league career. With an overall WAR (Wins Above Replacement) value of just 10.7, the first round of the 1975 draft easily was the worst on record (at 61.9, 1970 was next). Only three players, catcher Rick Cerone, outfielder Clint Hurdle and infielder Dale Berra, had careers of at least 10 years—though barely. Perhaps most curious, big-league teams saw fit to sign more players that year to major-league contracts (six, including Goodwin) than any draft in history, though all six did eventually reach the big leagues, including four that year. If there was any salvation, future Hall of Famer Andre Dawson came out of that year’s draft, though he was miscast as an 11th-rounder, while one-time career saves leader Lee Smith went in the second round, future American League batting champion Carney Lansford was taken in the third and five-time all-star Lou Whitaker went in the fifth.

22. 67,000 and counting . . .
In 49 drafts to date, there have been 67,557 players drafted. Another 1,216 should be added once this year’s proceedings are complete, assuming that all 30 major-league clubs will draft their full allotment through 40 rounds. The number of players drafted through the years has varied, depending on the number of allowable rounds—though there was no limit through 1991, and from 1993-97. In 1992, and again from 1998-2011, there were 50 rounds. Since 2011, the draft has been confined to 40 rounds. The most players drafted in any year occurred in 1996, when there were 1,740 selections. Last year’s total of 1,216—the same as this year’s anticipated mark—was the smallest since the draft was consolidated from four phases to one in 1987. Prior to that, the fewest number of draft picks occurred in 1974, when 1,020 players were selected overall, and just 726 in the June, regular phase.

23. Look Who’s Picking No. 1
The Houston Astros pick first overall in this year’s draft, marking the first time that a team has had the top selection in three consecutive years. They earned the dubious distinction by finishing with the worst record in the big leagues in each of the last three years, posting the only 100-loss seasons in club history in the process. Previously, the Tampa Bay Rays (2007-08) and Washington Nationals (2009-10) were the only teams to pick first in consecutive years, though the practice would have happened in previous years had Major League Baseball always awarded the top pick to the major-league team with the poorest record. Prior to 2005, the pick alternated yearly between National and American League teams. By drafting first again, the Astros tie the New York Mets and San Diego Padres as teams that have had the top pick five times over the life of the draft. Pittsburgh, Seattle and Tampa Bay have selected first four times. Meanwhile, Boston, Cincinnati, Cleveland, Colorado, the Los Angeles Dodgers. St. Louis, San Francisco and Toronto have never selected first overall.

24. Risky Demographic I: High-School Righthanders
It speaks volumes about the risky nature of drafting high-school right-handers that not a single player in that demographic has ever been selected No. 1 overall, though a prep righty has gone second on seven occasions, most prominently J.R. Richard in 1969 and Josh Beckett in 1999. No high-school righthander drafted anywhere in the first round has been selected to the Hall of Fame, though Rick Sutcliffe (1973), Dwight Gooden (1982), Kerry Wood (1995), Roy Halladay (1995), Adam Wainwright (2000), and Zack Greinke (2002) have had noteworthy careers, and the recently-retired Halladay, in particular, appears destined for Cooperstown. Despite being shut out on first-rounders, the Hall of Fame does include four prep right-handers from the draft era that are enshrined, in Nolan Ryan (1965/10th round), Bert Blyleven (1969/third round), Goose Gossage (1970/ninth round) and Dennis Eckersley (1972/third round), and Greg Maddux (1982/second round) will make it five when inducted in July. Of the grand total of 188 high-school right-handers drafted in the first round between 1965 and 2009 (no allowance has been made for pitchers drafted from 2010-13 to give them a fair chance to reach the big leagues), only 118, or 62.7 percent, have played in the big leagues. By contrast, 27 first-round prep right-handers in the draft era never advanced in the minor leagues beyond Class A.

25. Misguided Intentions Set Tone for Yankees Drafts
The draft strategy of the New York Yankees during George Steinbrenner’s early ownership reign was often a factor of (a.) his fixation for football players (he was an assistant coach in college in his younger days), (b.) penchant for stretching rules to his and his club’s advantage, (c.) general loathing for a draft system that prevented the Yankees from gaining access to their share of the best-available amateur talent and (d.) the heavy investment the Yankees annually made in the major-league free-agent market, which routinely came at the expense of a first-round pick.

The period from 1979-82, in particular, provides a colorful sidebar into Steinbrenner’s penchant for meddling. The Yankees forfeited every one of their top-round selections in those years, yet never failed to create their share of draft headlines. In 1979, the Yankees drafted power-hitting Oklahoma high-school first baseman Todd Demeter, son of ex-big leaguer Don Demeter, in the second round after he conveniently fell into their lap when other teams passed on him in the first round after determining his price tag was too extravagant. The Yankees, undeterred, promptly forked over a then-draft record $208, 000 bonus to sign Demeter, who briefly rose as high as Double-A in seven seasons in the Yankees system.

A year later, the draft tactics of the Yankees became highly suspicious when they didn’t have a pick in either of the first two rounds, and yet were able to draft Billy Cannon, son of the former Heisman Trophy winner and one of the top talents in that year’s draft, in the third round. After an investigation by the commissioner’s office after several clubs blew the whistle on the Yankees, it was determined that the Cannon family had conspired with the Yankees to float out an artificially-high price tag for Cannon’s services that would make him unsignable in the eyes of other clubs, and enable him to slide to the Yankees. The selection was subsequently voided. The Yankees were the only team Cannon wanted to play for, had he signed to play baseball. He chose instead to play football in college and subsequently became a first-round draft pick of the NFL’s Dallas Cowboys.

In 1981, the Yankees took Stanford quarterback John Elway with their top pick (second round) and gave him a $75,000 bonus to play six weeks in their farm system. The Yankees hoped Elway might choose baseball over football by getting a taste of playing in their system, but Elway never played baseball again before going on to become the no. 1 pick in the 1983 NFL draft. In 1982, the Yankees took a flier on Bo Jackson in the second round, but made little headway in signing the Alabama football-baseball star before he went on to a record-breaking football career at Auburn. Like Elway, he would also become the no. 1 pick in the NFL draft, in 1986. In the end result, the Yankees had little to show for all their expensive free-agent forays, attempts to circumvent the traditional draft process and misguided dealings in trying to woo elite-level football players. But they did manage to make good, through the process of traditional scouting, on a lowly 17th-round pick in 1979: Don Mattingly.

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Regarding #3, David Clyde: Can anyone imagine what would happen if Brady Aiken went 1:1 and was immediately put into the Astros rotation?
Sorry, that's #4
I don't understand #16. Did the Yankees just keep submitting picks one after another until they used all their picks, regardless of order?
I think that's pretty much it -- the draft used to go until all teams "passed," so if the Yankees wanted players and no one else did they just kept naming names one after another until they were done.
I was hoping the Mark Prior/Joe Mauer draft would make the list... it was depressing as a Twins fans at the time, but turned out so well for us.
Thumbs up thanks.