The Biggest Draft Day Steals in MLB History

Baseball | 6/14/19

Major League Baseball held its first amateur draft in 1965 and it has always been an inexact science. Players drafted in the top few picks may never even make the big leagues. Players drafted in the far later rounds of the draft have gone on to have Hall of Fame careers. While some of these later picks are legendary, others may not be as well known by fans. Starting from the very first draft in 1965, here is a list of those players that fell through the cracks on draft day, but handsomely rewarded the teams that selected them.

Jeff Conine – 1987, Round 58

Phillies v Marlins
Photo by Eliot J. Schechter/Getty Images
Photo by Eliot J. Schechter/Getty Images

Conine not only carved out a quality 17-year career, but he also served as the very first captain and all-star for the expansion Miami (then Florida) Marlins. He also became the Most Valuable Player of the 1997 World Series Championship team.

From there, he was dealt to the Baltimore Orioles. The outfielder was traded back to the Marlins in 2003, just in time to help them capture their second World Series flag. Conine retired from the game in 2007 having hit 214 homers, amassing 1,071 RBI’s and earning 22.1 Wins Above Replacement. He is still affectionately known as Mr. Marlin down in Miami.

Bret Saberhagen – 1982, Round 19

1985 World Series:St. Louis Cardinals v Kansas City Royals, October 27, 1985
Photo by Focus on Sport/Getty Images
Photo by Focus on Sport/Getty Images

Saberhagen was a fast riser for Kansas City making the major leagues at the tender age of 19. By age 21 he had captured his first Cy Young Award and by the end of 1985, he’d become the Most Valuable Player for the World Champion Royals.

In 1989, he again won the American League Cy Young Award after winning 23 games and posting an ERA of 2.16. Saberhagen was dealt to the Mets in a 1992 blockbuster deal. The right-hander pitched until 2001, remaining a quality starter but never quite reaching the heights he’d scaled as a member of the Royals.

Jose Canseco – 1982, Round 15

Rockies v Athletics
Photo by Otto Greule Jr/Getty Images
Photo by Otto Greule Jr/Getty Images

Early on in his career, it seemed that Canseco would appear much higher on this list. As part of the Bash Brothers with Mark McGwire, Canseco powered the Athletics to 3 straight World Series appearances (1988, 1989, 1990) winning the title in 1989.

Canseco also captured the 1988 American League MVP Award on the strength of his 42 home runs and 40 stolen bases. The later years of the slugger’s career were marred by serious injuries and accusations of steroid abuse (which Canseco later confirmed). Still, the Outfielder had a very successful career totaling 462 homers in his 16 career seasons.

The next slugger, known as the Hawk, was elected to the Hall of Fame in 2010.

Andre Dawson – 1975, Round 11

Montreal Expos
Photo by Focus on Sport/Getty Images
Photo by Focus on Sport/Getty Images

Dawson moved fast through the Montreal Expos’ farm system quickly, becoming a full-time player for the club in 1977. He was a success right away, winning that year’s Rookie of the Year Award in the National League. The slugger was seen as a 5 tool player who combined power, speed and a cannon for an arm.

He captured the MVP Award in 1987 after he bashed 49 home runs for the Chicago Cubs. The middle and latter part of Dawson’s career, however, was diminished by chronic knee issues. Dawson, though, had already done enough in his 21-year career to be elected into the Baseball Hall of Fame in 2010.

Wade Boggs – 1976, Round 7

Boston Red Sox
Photo by Focus on Sport/Getty Images
Photo by Focus on Sport/Getty Images

While Boggs may not have been drafted as late as some of the other names on this list, he can still be considered an enormous steal for the Red Sox. Boggs was a superstar from his first season in 1982 when he hit .349. The career .328 hitter played 11 seasons in Boston, appearing in the World Series in 1986 and winning 5 American League batting titles.

Boggs then moved on to play for the hated Yankees in 1993. While there, he captured a World Series title while playing for New York in 1996. He was elected to the Hall of Fame, with 91% of the vote in 2005.

Dusty Baker – 1967, Round 26

MLB: OCT 06 NLDS Game 1 - Cubs at Nationals
Photo by Tony Quinn/Icon Sportswire via Getty Images
Photo by Tony Quinn/Icon Sportswire via Getty Images

Since beginning his career with the Atlanta Braves in 1967, Baker has had a profound impact on Major League baseball. The powerful Outfielder hit 242 home runs over the course of his career and made All-Star teams in 1981 and 1982. 1981 also saw Baker capture a World Series ring as a member of the Los Angeles Dodgers.

Following his playing career, Baker became a very successful manager for the San Francisco Giants, Chicago Cubs, and Washington Nationals. The teams he managed have an overall winning percentage of .532 and made numerous playoff appearances. Baker’s teams, however, never captured a World Series Title.

The next player, affectionately known as Pronk, terrorized American League pitching in the mid 2000’s

Travis Hafner – 1996, Round 31

Cleveland Indians v. Kansas City Royals
Photo by John Williamson/MLB Photos via Getty Images
Photo by John Williamson/MLB Photos via Getty Images

Hafner, from tiny Jamestown, North Dakota, had to work extra hard to be discovered by pro scouts. While he was drafted by the Texas Rangers, his biggest success came with the Cleveland Indians. “Pronk” was one of the premier hitters in the game between 2004-2007 pairing massive home run power with a sharp batting eye.

His best season came in 2006 when he hit 42 homers, scored 100 runs, knocked in 117 and sported an eye-popping .1098 OPS. That same year he also set an MLB record with a total of 6 Grand Slams. While his later career was beset with injuries, Hafner retired with 213 home runs and an .874 OPS.

Roy Oswalt – 1996, Round 23

Houston Astros v Chicago Cubs
Photo by Jonathan Daniel/Getty Images
Photo by Jonathan Daniel/Getty Images

Despite his big ability, Oswalt was largely ignored by scouts due to his lack of height and slim frame. The Houston Astros took advantage and were rewarded with rewarded with 10 seasons of ace-like results from the right-hander. Oswalt, who retired with a career ERA of 3.36 appeared in 3 straight All-Star games for Houston (2005-2007).

The pitcher was traded to the Phillies and spent the next two years pitching in tense playoff games for Philadelphia. Oswalt spent time with the Texas Rangers and Colorado Rockies during the latter part of his career. The skinny pitcher from Weir, Mississippi finished with a career record of 163-102.

Kenny Lofton – 1988, Round 17

ALCS: Boston Red Sox v Cleveland Indians, Game 3
Photo by John Reid III/MLB Photos via Getty Images
Photo by John Reid III/MLB Photos via Getty Images

After a star-studded career at Arizona State, Kenny Lofton had options of what to do with his life. He was the starting Point Guard on the basketball team only started playing baseball in his Junior year. He showed enough for the Indians to draft him. It ended up being a very shrewd decision for Cleveland.

Lofton, who finished his career with 622 stolen bases, was the leadoff hitter and catalyst for Cleveland’s 1997 World Series runner-up. He later played for a number of different organizations. A 6 time All-Star and 4 time Gold Glover, Lofton was elected to the Cleveland Indians Hall of Fame in 2010.

Andy Pettitte – 1990, Round 22

Tampa Bay Rays v New York Yankees
Photo by Adam Hunger/Getty Images
Photo by Adam Hunger/Getty Images

As a lefty whose game was more about finesse than power, Pettitte was snapped up by the New York Yankees during the later rounds of the 1990 draft. He did not make his first appearance for the team until 1995, but then became a rotation mainstay for the Yankee dynasty of the late 1990s.

The left-hander was a part of five World Series winning teams with the Yankees. Pitching mostly for New York, with a short stop in Houston, Pettitte finished his career with a record of 256-153. The Yankees rewarded Pettitte for his fine career with a plaque in Monument Park.

Don Mattingly – 1979, Round 19

New York Yankees...
Photo by Focus on Sport/Getty Images
Photo by Focus on Sport/Getty Images

Don Mattingly was a highly ranked Indiana High School prospect, but he lasted until the 19th round after his father told teams he would be attending college. The Yankees took a chance that they could change their mind and succeeded. Mattingly was a superstar during his 14 years with the Yankees.

He appeared on 6 All-Star teams, won 9 Gold Gloves and was the 1985 American League MVP when he hit .324 with 35 homers and knocked in 145 runs. Unfortunately for both Mattingly and the Yankees, his career was derailed by a diagnosis of spinal stenosis. His number 23, was retired by the team in 1997.

The next draft pick had 1,754 hits in the 1990’s, more than any other player.

Mark Grace – 1985, Round 24

Mark Grace looks on
Photo by Tom Pidgeon/Getty Images
Photo by Tom Pidgeon/Getty Images

When the Cubs drafted Mark Grace in 1985, little did they know that they would be getting a player who would remain with the franchise for the next 16 years. Grace provided the Cubs with a high batting average and steady defense. The First Baseman finished his career with 3 All-Star appearances and 4 Gold Glove Awards.

Grace moved on to the Diamondbacks at the end of his career and was able to win a World Series championship with Arizona in 2001. He retired from the game with a total of 2,445 career hits and a lifetime batting average of .303.

Jeff Kent – 1989, Round 20

Jeff Kent #21
Mandatory Credit: Tom Hauck /Allsport
Mandatory Credit: Tom Hauck /Allsport

Jeff Kent, who was thrown off his High School baseball team, lasted until the 20th round of the 1989 draft. The Second Baseman made his MLB debut in 1992 but didn’t truly break out until his 1998 season with the San Francisco Giants. From ’98 through the end of his career in 2008, Kent was one of the more feared hitters in the National League.

The right-handed hitter appeared in 5 career All-Star games and was the 2000 National League MVP. Kent retired with a .290 career batting average to go along with 377 home runs, 1,320 runs scored and 1,518 RBI’s.

Ken Griffey Sr. – 1969, Round 29

Seattle Mariners v Oakland Athletics
Photo by Focus on Sport/Getty Images
Photo by Focus on Sport/Getty Images

Unlike his son, Ken Griffey Jr. who was drafted first overall in 1987, Griffey Sr. lasted until the 29th round in 1969. Griffey made his Major League debut in 1973 for the powerhouse Cincinnati Reds. He captured World Series rings with the club during the 1975 and 1976 seasons.

He also made All-Star game appearances in 1976, 1977 and 1980 and was named to the Reds Hall of Fame in 2004. Griffey later played for the Yankees and Braves. During the end of his career, the outfielder became teammates with his son while playing with the Seattle Mariners in 1990 and 1991.

Keith Hernandez – 1971, Round 42

League Championship - Chicago Cubs v New York Mets - Game One
Photo by Elsa/Getty Images
Photo by Elsa/Getty Images

Keith Hernandez began his baseball career as the 776th pick of the 1971 draft and ended it as a New York sports icon. The First Basemen did give the team that drafted him, the St. Louis Cardinals, quite a few excellent years. That includes 1979 when he hit .344 and shared the National League MVP Award with Willie Stargell.

Hernandez was traded to the Mets in 1983 and captained them to a World Series title in 1986. A career .296 hitter and 11 time Gold Glover, Hernandez embraced the New York City spotlight and even appeared on a memorable episode of Seinfeld.

Mark Buerhle – 1998, Round 38

World Series Game 3: Chicago White Sox v Houston Astros
Photo by Brad Mangin/MLB Photos via Getty Images
Photo by Brad Mangin/MLB Photos via Getty Images

Mark Buerhle’s career began inauspiciously enough. The hurler went from being a very late round pick for the White Sox in 1998 to being a 16 game winner for the team on 2001. Over the next 10 seasons, Buerhle would pitch at the top of Chicago’s rotation.

Along the way, he won 161 games for the team, made a total of 5 All-Star games and led the team to a 2005 World Series championship. Buerhle also pitched a perfect game in 2009 and a no-hitter in 2007. The White Sox recognized Buerhle in June of 2017 by retiring his number 56.

Ryne Sandberg – 1978, Round 20

League Championship Series - Los Angeles Dodgers v Chicago Cubs - Game Four
Photo by Jonathan Daniel/Getty Images
Photo by Jonathan Daniel/Getty Images

The Phillies shrewdly selected Sandberg in the later rounds of the 1978 draft. Unfortunately for Philadelphia, he would only play 13 games for the club. As a member of the Chicago Cubs, who traded for him in 1982, Sandberg would become one of the greatest Second Basemen of all time.

The slugger appeared in 10 All-Star games and won 9 Gold Glove Awards. Sandberg also took home the 1984 NL MVP Award when he hit .314 with 19 homers, 114 runs scored, 84 RBI’s and 32 stolen bases. The Second Basemen was elected to the Hall of Fame in 2005.

Nolan Ryan – 1965, Round 12

MLB Photos Archive
Photo by Rich Pilling/MLB Photos via Getty Images
Photo by Rich Pilling/MLB Photos via Getty Images

Major League Baseball held its first amateur draft in 1965. The event also featured one of the draft’s all-time biggest steals when the Mets selected Nolan Ryan in the 12th round. While Ryan was a member of the Mets 1969 World Series team, he would be traded to the Angels in 1971.

Also pitching for the Houston Astros and Texas Rangers, the right-hander would go on to win 324 games. Ryan holds two records that may never be broken, seven no-hitters and 5,714 career strikeouts. A legend of the game, the big Texan was elected to the baseball Hall of Fame in 1999.

Albert Pujols – 1999, Round 13

Los Angeles Angels of Anaheim v Baltimore Orioles
Photo by Will Newton/Getty Images
Photo by Will Newton/Getty Images

When the Cardinals plucked Pujols from Maple Woods Community College in 1999, they could have never anticipated that they were getting one of the great power hitters of all time. The right-handed hitter spent very little time in the minor leagues, becoming an All-Star and the National League Rookie of the Year in 2001.

Along the way, Pujols would acquire two World Series rings (2006, 2011) and 3 MVP Award (2005, 2008, 2009). The slugger moved over to the Anaheim Angels in 2012 and his career has tapered off with age. Still, Pujols currently has a .301 career batting average with 644 home runs and 2,015 RBI’s.

Mike Piazza – 1988, 62nd Round

New York Mets v Atlanta Braves
Photo by Focus on Sport/Getty Images
Photo by Focus on Sport/Getty Images

When the Dodgers selected Piazza in the 62nd round, they weren’t looking to uncover a steal. The catcher was drafted as a favor from manager Tommy Lasorda to Piazza’s father. It turned out the be the greatest draft steals of all time. Piazza became the 1993 Rookie of the Year by hitting .318 with 35 homers and 112 RBI’s.

The catcher displayed a rare combination of power and general hitting ability. The 12-time All-Star was traded to the New York Mets in 1997 where he continued his dominance at the plate. Finishing his career with 427 home runs and a .308 batting average, Piazza was inducted into the Hall of Fame in 2016.