The 10 best late-round draft picks ever, led by Mike Piazza, and a new way to measure them

Mike Piazza was chosen in the 62nd round in 1988 before becoming a Hall-of-Fame-caliber star with the Dodgers and Mets. (John Iacono/SI) Baseball's 2014

Mike Piazza was chosen in the 62nd round in 1988 before becoming a Hall-of-Fame-caliber star with the Dodgers and Mets. (John Iacono/SI)

Baseball's 2014 amateur draft concluded on Saturday with rounds 11 to 40, and it could take the rest of the decade before we know who if any of them will become contributing major leaguers. With that in mind, I wanted to identify the best late-round picks of the previous 49 drafts, to give a sense of what kind of talent could emerge from that final day.

To do so, I had to weigh each player's performance against his draft position, as the bar for a successful pick is lower the deeper you get into the draft. The solution I came up with is a statistic I'm calling DROP, or Draft Round Opportunity Points. It is obtained very simply by multiplying a player's career wins above replacement by the round in which he is drafted. The higher the DROP, the better the pick.

Draft round alone isn't a precise measure of how late a player was chosen. Because of expansion and various supplemental rounds and compensation picks, the number of selections in a single round of the draft has changed dramatically over the last half century. For example, in the first four years of the draft, the first round consisted of just 20 picks, one for each team. In 2013, there were 39 first-round picks, including six competitive-balance picks, a compensation pick for an unsigned first-rounder from the previous year and various adjustments for free-agent compensation. Still, using DROP I was able to calculate the value of every pick in the draft's history to present the following definitive list of the best late-round picks in major league history (you can find a more extensive leader list here).

A few fun facts before we get to the list. Prior to 1998, teams could draft as many players as they wanted provided they did so in turn, so every draft from the first in 1965 to 1997 was a different length. That changed in 1998, when the draft was limited to 50 rounds. It was further reduced to 40 rounds in 2012. The reason for the institution of the hard limit was that the drafts in the early '90s were getting out of control, as evidenced by the 1996 draft, which boasts the following distinctions:

• The most picks ever and the longest draft ever, going a full 100 rounds. However, only the Yankees and Rays lasted past the 83rd round. The final four rounds, 97 through 100, each consisted of a single pick by the Yankees.
• The latest draft pick in Rule 4 history. Aron Amundson, a third baseman out of East Oklahoma State College, was taken by the Yankees in the 100th round with the 1,740th pick. According to baseball-reference.com, Amundson played two of independent ball, but he did make it to the major leagues in 2001 as the Twins' bullpen catcher.
• The latest pick to make it to the majors as a player. Righthanded pitcher Travis Phelps was drafted out of Crowder College by the Rays with the 1,721st overall pick in the 89th round. Phelps had a strong rookie season in the Tampa Bay bullpen in 2001 before washing out of the league three years later. Numerous players have made the majors after going undrafted, which has become more common since the length of the draft has been limited. The most notable recent example is Braves pitcher Brandon Beachy, who signed as an undrafted free agent in 2008.
• The latest pick to have a 10-year career in the majors. Former Indians reliever David Riske, taken in the 56th round, appeared in 462 games over 11 seasons, posting a 121 career ERA+.
• The latest pick to have a career worth 10 or more WAR. Former Braves second baseman Marcus Giles, little brother of Pirates slugger Brian (who was drafted 17th overall in 1989), was chosen in the 53rd round with the 1,512th overall pick. Giles was an All-Star in 2003 and compiled 15 bWAR from 2003 to '05, but ultimately played just seven major league seasons.

On with the list . . .

1. Mike Piazza, 1B, Dodgers, 1988

62nd round, 1,390 overall

bWAR: 59.4

DROP: 3,683

Piazza wasn't the last player chosen in the 1988 draft, but he was the Dodgers' last pick, and one that was only made as a courtesy to manager Tommy Lasorda, who had been a friend of Piazza's father since the late 1960s. Had it not been for that connection, the greatest hitting catcher in major league history likely would have gone undrafted and may never have had a major league career. As Lasorda tells it in Piazza's recent autobiography (titled Long Shot, a reference to his draft position), "I sent five of my friends from five different organizations out to see Michael play, and nobody wanted to sign him. I ordered the Dodgers to draft him. I said 'I don't give a [hoot] where you draft him, but draft him. They weren't doing me a favor, I was doing them a favor."

Even after the draft, Lasorda still had to convince Los Angeles to actually sign Piazza as well as convince everyone involved, Piazza included, that he should and would become a catcher. As an amateur, Piazza had obvious power, but was a lousy defensive first baseman whom scouts didn't think would be able to hit professional pitching. They were never more wrong, as his 427 home runs and .296 career average will attest.

2. Keith Hernandez, 1B, Cardinals, 1971

42nd round, 785 overall

bWAR: 60.0

DROP: 2,520

An 11-time Gold Glove winner who is generally considered one of, if not the, best defensive first basemen in major league history, Hernandez's fielding prowess is not reflected in the advanced statistics. One reaction to that is that bWAR may be underrating him, meaning his DROP should be even higher. As it is, he's a borderline Hall of Famer (50.5 JAWS vs. the first base standard of 54.2) who was a five-time All-Star, the co-MVP of the National League in 1979 and a two-time World Series champion (1982 Cardinals and 1986 Mets).

Hernandez fell in the draft because he was labeled a problem child after he sat out his senior year of high school due to a dispute with his coach. That label wasn't inaccurate. Hernandez abused cocaine in the early '80s, prompting Cardinals manager and GM Whitey Herzog to trade him for pennies on the dollar to the division-rival Mets in June 1983, supposedly without regret. On photo day in 1989, he got in a fistfight with former top overall pick Darryl Strawberry, and he has since gotten himself into occasional hot water for things he has said while broadcasting Mets games. However, none of that changes the fact that of all the players chosen in 1971, only Hall of Fame third basemen Mike Schmidt and George Brett had more valuable major league careers.

3. Mark Buehrle, LHP, White Sox, 1998

38th round, 1,139 overall

bWAR: 56.8

DROP: 2,158

Buehrle was a draft-and-follow player. Under that since-eliminated rule, teams were able to draft a player and keep tabs on his progress for a year, right up until the week prior to the following year's draft, before deciding whether or not to sign him. Instituted before the 1987 draft, the rule was one reason the drafts in the early '90s swelled to such a degree. It was abolished before the 2007 draft.

Buehrle ultimately signed with the White Sox for $167,000 on May 21, 1999, proof that the team valued him well above the level of his draft round. Still, Buehrle is a player who has consistently exceeded expectations throughout his career -- right up to this season, in which he is 10-1 with a 2.10 ERA -- and rates as a miss on the part of the scouts.

John Sickels, author of the annual Baseball Prospect Book, admitted as much in a look back at Buehrle's prospect evaluations last April, confessing that, even after Buehrle's solid major league debut in 2000, he didn't think much of the pitcher.

his stuff was nothing special, with a mediocre fastball and an assortment of adequate but not excellent off-speed pitches. . .  I remember thinking that Buehrle was a fluke of some kind and that in the long run he would be an average pitcher, at best. He didn't throw that hard, and his strikeout rate was very low. Usually, even a successful finesse pitcher still has a decent strikeout rate. I was convinced that the hitters would eventually catch up with him and figure out how to beat him.

They never did.

Buehrle has won 196 major league games, thrown a perfect game and a 27-batter no-hitter, made four All-Star teams, won four Gold Gloves, is one of the most durable pitchers in major league history and at the age of 35 is once again one of the best pitchers in the American League. He was still severely underdrafted.

4. Kenny Rogers, LHP, Rangers, 1982

39th round, 816 overall

bWAR: 51.4

DROP: 2,005

It's a miracle that Rogers was drafted at all. He didn't play baseball until his senior year of high school and was only noticed by the Rangers because they had come to his town to scout another player and were impressed enough by his arm strength at shortstop to consider drafting him as a pitcher. When selected, he was a 135-pound 17-year-old with virtually no pitching experience. Twenty-six years later, he retired with 219 major league wins, four All-Star appearances, five Gold Gloves and a perfect game to his credit. Of all the players on this list, Rogers stands as the most remarkable example of what scouting can do.

5. John Smoltz, RHP, Tigers, 1985

22nd round, 574 overall

bWAR: 69.5

DROP: 1,529

Before the 1985 draft Smoltz signed a letter of intent to play baseball (and try basketball) at Michigan State. Without it, Sickels estimates that Smoltz would have gone in the first five rounds. Even after his favorite team drafted him in the 22nd round, he held out for first-round money, ultimately signing on the eve of what would have been his first day of college. Ironically, he was traded to Atlanta just two years later in the infamous deal that brought Detroit 36-year-old Doyle Alexander, who helped the Tigers win the 1987 AL East title. Smoltz, of course, went on to a Hall of Fame career, almost entirely with the Braves.

6. Ryne Sandberg, 2B, Phillies, 1978

20th round, 511 overall

bWAR: 67.5

DROP: 1,350

Sandberg's story greatly resembles Smoltz's. He dropped in the draft due to a letter of intent to attend college, was drafted in the middle rounds and was traded away before the vast majority of what was ultimately a Hall of Fame career (Smoltz isn't eligible for the Hall yet, but he'll join Sandberg there soon after he is). In Sandberg's case, he had planned to play quarterback for Washington State, but he took the Phillies' money instead. His $24,000 bonus was more than a third of the average bonus received by a first-round pick.

7. Andy Pettitte, LHP, Yankees, 1990

22nd round, 594 overall

bWAR: 60.8

DROP: 1,338

Like Buehrle, Pettitte was a draft-and-follow lefty who consistently exceeded expectations. He signed for $80,000 on May 25, 1991, then went on to win 256 major league games, finish in the top six in the Cy Young voting six times, pitch on 14 playoff teams in 18 seasons, win eight pennants, five World Series titles and start and win more postseason games than any other pitcher in major league history. Two rounds later in the same draft, the Yankees pulled the same trick with a Puerto Rican shortstop named Jorge Posada, whom they then watched play a season for an Alabama community college before signing him for about $3,000. Posada became a five-time All-Star catcher for New York and ranks 19th all-time in DROP.

8. Orlando Hudson, SS, Blue Jays, 1997

43rd round, 1,280 overall

bWAR: 30.9

DROP: 1,329

The most fascinating thing about Hudson's draft position is that he was actually taken 10 rounds earlier by the Blue Jays the previous year but did not sign. When selected again in 1997, he was a draft-and-follow, so he ultimately didn't sign until two years after Toronto first tried to draft him. A two-time All-Star and four-time Gold Glove winner, Hudson had an average bat but was a defensive specialist who had a very valuable 11-year major league career for six teams, averaging just under four wins above replacement from 2003 to '10.

9. Albert Pujols, 3B, Cardinals, 1999

13th round, 402 overall

bWAR: 94.5

DROP: 1,229

Compared to draft position of the first eight men on this list, the 13th round doesn't sound that late, but consider that if you were to have a draft of every major league player in history, Pujols would go in the top 50. In the 1999 draft, he didn't make the top 400. To be precise, there were 401 players taken ahead of Pujols that year. Every team in baseball had a dozen chances to draft him, and half of them had a 13th before the Cardinals finally took him with the 18th pick of the 13th round. It's unfathomable now, but the scouts weren't completely sold on him. They cited questions about his age and described him as having a bad body and a long swing. That swing has helped him rank in the top 10 in career OPS+ and, at the age of 34, in the top 25 all-time in WAR for hitters.

10. Kenny Lofton, CF, Astros, 1988

17th round, 428 overall

bWAR: 68.2

DROP: 1,159