In a sport where every June each team selects approximately 40 players, there is sure to be a number of “what ifs”. Players frequently spend at least 3 or 4 years honing their skills in the minor leagues prior to being called up to the Majors. Over that time, players improve and evolve and often even learn a new position in order to meet organizational needs. Due to these almost expected changes, players are drastically different than when they were drafted. This is the story of how a player who was drafted 279 can make multiple All-Star appearances.
Much as Hercules struggled to complete The Twelve Labours, general managers are faced with an even more challenging task, with the consequences of failure, being just as dire. As Hercules faced the Nemean lion, general managers must resist the lure of drafting a player who will choose college. General Managers can also empathize with the hopelessness of battling the Lernaean Hydra when faced with a seemingly endless pool of players. Once drafted keeping them in your organization and avoiding the Rule 5 Draft, is as difficult as chasing the Ceryneian Hind.
Due to the labors of General Manager exceeding those of Hercules, there is no wonder there are so many ‘what ifs’ in Major League Baseball. This article will make note of the biggest draft day ‘steals’ each team has had since 2000. In order to ensure all general managers are evaluated equally and to prevent a single player from representing multiple teams, only players in which the club actually signed are officially considered a ‘steal’.
31 Arizona Diamondbacks: Paul Goldschmidt
Despite being drafted by the Los Angeles Dodgers three years earlier ‘Goldy’ never signed a contract to wear Dodger blue. Such an action might have been the reason why the Diamondbacks were able to draft the 6’3’ first baseman in the 8th round with the 246th overall pick.
Six All-Star selections, 3 Gold Gloves and 3 Silver Slugger awards later the Diamondbacks are still benefiting to this day.
With the newly installed humidor, Goldschmidt might be wishing he signed with the Dodgers.
30 Atlanta Braves: Craig Kimbrel
The Atlanta Braves know a good thing when they see it. In 2007 they drafted Craig Kimbrel out of Wallace State Community College but were unable to come to an agreement with their 33rd round selection. Not ones to give up hope, they drafted Kimbrel a year later, at a slightly more costly price in the third round. Even in the third round, Kimbrel was a big steal. During his five seasons with Atlanta, ‘Dirty Craig’ would win the Rookie of the Year and make four All-Star teams.
29 Baltimore Orioles: Jake Arrieta
When the Orioles traded the 20-25 Jake Arrieta to the Chicago Cubs, they were not under the belief their 5th round pick of seven years ago was a steal. The 6’4” righty accumulated a 68-31 record with a 2.73 ERA over his five seasons with the Cubbies. His bat picked up too, as he won a Silver Slugger in 2016 when he went to the All-Star game. But those accomplishments pale in comparison to the Cy Young Award he won in 2015.
28 Boston Red Sox: Mookie Betts
The Red Sox had some steals prior to Betts, they just were not able to sign them. In 2007, they drafted Anthony Rizzo in the 6th round, and in 2005 they drafted a left-handed pitcher in the 20th round, by the name of Charlie Blackmon.
In 2011, they drafted Betts in the 5th round and he has rewarded them to the tune of over 100 home runs, 3 All-Star games, 2 Gold Glove awards and a Silver Slugger in his five seasons.
And there's still plenty more to come from him.
27 Chicago Cubs: Dontrelle Willis
With the 223rd overall pick in the 2000 MLB Draft, the Chicago Cubs selected a hard-throwing left-handed pitcher out of Encinal High School. Unfortunately, the 8th round selection would never play for the Cubs, as he was traded two years later to the Florida Marlins. Little over a year later, the 21-year-old would make his debut for the Marlins and ultimately win the Rookie of the Year and a World Series in 2003. All in all, Willis had a solid career that no one foresaw.
26 Chicago White Sox: Chris Sale
When Chris Sale was originally drafted by the Colorado Rockies with their 21st round pick in 2007, it was a much bigger steal, but he did not sign. So, when the White Sox selected Sale with the 13th overall pick a few years later, it was at a higher price, but still considered a steal when the six pitchers selected before him have a combined total of 3 more wins. Sale would go 74-50 with the White Sox and attend five All-Star games.
25 Cincinnati Reds: Joey Votto
Votto was not some diamond in the rough discovered by the Cincinnati Reds in 2002.
He makes this list because the Reds have been unable to sustain any success drafting.
The players drafted by the Reds who went on to have the most success in the MLB around the year that Votto was selected are; Dustin Moseley, Nick Markakis, and Ryan Wagner. Although, when you select Chris Gruler with the 3rd overall pick and still get Votto in the 2nd round, that is a steal.
24 Cleveland Indians: Cody Allen
In 2010 the Cleveland Indians drafted a 6’1’ right-handed pitcher out of St. Petersburg College in the 16th round but were unable to come to terms. So, fast forward a year and the Cleveland Indians drafted a 6’1” right-handed pitcher out of High Point University in the 23rd round.
Despite having to use a draft pick in consecutive years to attain the services of Cody Allen, he remains a steal for them.
He's been one of the game's elite closers, but unfortunately for the Indians, they may be about to lose him in free agency.
23 Colorado Rockies: Nolan Arenado
Todd Frazier in 2004 with their 37th round pick was fantastic, Chris Sale in 2007 in the 21st round was better, but the Rockies signed neither. Nolan Arenado however, signed after being drafted in the 2nd round of the 2009 MLB draft.
Even after accounting for the career .291 batting average, 182 home runs, 4 All-Star selections, 5 Gold Gloves and 3 Silver Slugger awards, the fact that the Rockies chose Tyler Matzek, Tim Wheeler, and Rex Brothers before Arenado, makes him a steal.
22 Detroit Tigers: Justin Verlander
Before you skip the next paragraph to find out when Justin Verlander was drafted, let it be stated that the former Rookie of the Year, MVP, Cy Young, Triple Crown winner, 7-time All-Star, ALCS MVP had a 183-114 record with a 3.49 ERA over his 13 years with the Detroit Tigers, who happened to draft him 2nd overall.
When the Tigers reflect, they must feel like they stole one from the San Diego Padres, who drafted Matt Bush #1 overall.
20 Houston Astros: Dallas Keuchel
The 2009 MLB June Amateur Draft was one to remember for Houston Astros fans. That year they drafted J.D Martinez in the 20th round, who would go on to hit .251 with 24 homers in his three years in Houston.
However, the Astros also selected future Cy Young Award winner Dallas Keuchel in the 7th round with pick no.221.
Unlike Martinez, the Astros did not release Keuchel in 2014 and he has been in Houston for his 3 Gold Gloves and 2 All-Star appearances.
19 Kansas City Royals: Whit Merrifield
Forget about a ‘steal’, finding a decent pick in Royals’ drafting history is difficult. The Royals did select Whit Merrifield in 2010 with the 269th selection. It may not be impressive that a 9th round selection has 33 home runs, 164 runs batted in, with a career batting average of .290, but once you take into consideration that only eight players drafted by the Royals between 2005-2011 have appeared in more than 100 MLB games, Merrifield is looking pretty good.
18 Los Angeles Dodgers: Matt Kemp
Matt Kemp’s first stint with the Dodgers began with a 6th round selection in 2003 and ended when they traded him to the San Diego Padres in 2014. In those years Kemp was a 2-time Gold Glove and 2-time Silver Slugger winner while being selected to 3 All-Star games.
Still, if David Price would have signed in 2004 after being selected in the 19th round, or Paul Goldschmidt after a 49th round selection in 2006, Kemp would not be the Dodgers’ biggest steal.
17 Los Angeles Angels: Mike Trout
In 2009 Mike Trout was not selected #1 overall, in 2009 Mike Trout was not even the first center fielder selected, that distinction goes to #2 overall pick Dustin Ackley and #3 overall pick Donovan Tate.
Mike Trout, who would go on to win Rookie of the Year with the Angels, then be a 2-time MVP, 7-time All-Star, 5-time Silver Slugger, and arguably be the best player in baseball, after being selected 25th overall.
Twenty-four teams in the majors are kicking themselves.
16 Miami Marlins: Giancarlo Stanton
The Marlins took the opportunity in 2004 to select Charlie Blackmon in the 28th round, but such as he would the following year with Boston, he would not sign.
The next closest selection to a 'steal' was in 2007 with the selection of Giancarlo Stanton with pick no. 76. An MVP, four All-Star selections, and two Silver Slugger awards are not abnormal for a 2nd round pick, but they did select Matt Dominguez 12th overall. Nevertheless, Stanton was a gem they found after every team passed on him.
15 Milwaukee Brewers: Khris Davis
The Milwaukee Brewers got an absolute steal when they drafted Khris Davis with the 226th selection in the 7th round of the 2009 MLB Amateur Draft.
Do not give them too much credit, for they would trade him to Oakland, for Bubba Derby and Jacob Nottingham before he started to produce.
The 5’10” left fielder would play 1,142 games in Milwaukee and hit 62 home runs and knock in 162. His first season with Oakland, he hit 42 home runs with 102 RBI. He has surpassed both those totals this season.
14 Minnesota Twins: Brian Dozier
The Twins cannot be accused of not trying, because they know a good thing when they see it, they just are unable to sign that good thing. In 2006 they drafted J.D Martinez in the 36th round, then in 2008, they drafted George Springer in the 48th round, two outstanding steals, who both did not sign.
In 2009, the Twins would finally be able to sign a pretty good steal after drafting Brian Dozier in the 8th round. Dozier spent six-plus seasons in Minnesota before being traded to the Dodgers this summer.
13 New York Mets: 2010 - Jacob DeGrom
The 2009 MLB season saw the New York Mets go 70-92. The Mets knew they needed pitching and the 2010 MLB Amateur Draft would be the time to get it. They used the following rounds to select a right-handed pitcher; 1,5,6,7,8,9 and 10.
Their former first-round pick Matt Harvey has surpassed 40 career wins, but it was their 9th round pick Jacob DeGrom who would win Rookie of the Year in 2014 and become a 2-time All-Star.
12 New York Yankees: Tyler Clippard
The easy narrative is that the Yankees do not draft, but buy players, but recent stars like; Aaron Judge was selected 32nd overall, Gary Sanchez was signed as an amateur free agent, and Didi Gregorius was acquired in a trade.
The closest thing to a steal was drafting Tyler Clippard in the 9th round in 2009.
He would only start 6 games before being traded to the Nationals where he would be selected to 2 All-Star games. So unfortunately the Yankees couldn't reap the benefits from this steal.
11 Oakland Athletics: Rich Harden
Drafting Aaron Judge with the 935th selection in 2010 was a tremendous find and one of the greatest steals with regards to current players. Alas, he did not sign in Oakland; perhaps ‘Moneyball’ does not allow for the signing of 9th round picks, or Judge just wanted to go to California State University.
Either way, right-handed pitcher Rich Harden who was drafted in the 17th round and would accumulate 31 wins over 5 seasons with the As, so he gets the spot as their biggest steal since 2000.
10 Philadelphia Phillies: Ryan Howard
Any time a team drafts a future Rookie of the Year who will also become an MVP, a 3-time All-Star and a Silver Slugger award winner, all while playing for their team, the draft is an instant success. Oh, and Howard was also a huge part of their 2008 World Series win.
The fact that the Phillies were able to get 382 home runs and 1,194 runs batted in and all it cost them was using a 5th round pick in the 2001 draft, is the definition of a steal.
9 Pittsburgh Pirates: Jose Bautista
In 2000 the Pirates drafted a 6-time All-Star and 3-time Silver Slugger award winner in the 20th round.
The future 50 home run man would become eligible for the rule 5 draft in 2003, and the Orioles took advantage.
Then, between June 3rd and July 30th of 2003, ‘Joey Bats’ would be; selected off waivers, purchased then traded twice before arriving back in Pittsburgh.
He would play 400 games and hit 43 home runs before the Pirates traded him to the Blue Jays in 2008. Big mistake.
8 San Diego Padres: Corey Kluber
Thanks to supplemental picks, the Padres had 11 picks in the first 4 rounds of the 2007 MLB Draft. With their 10th selection that day, the Padres would select Corey Kluber 134th overall. Kluber has gone on to be a 2-time Cy Young winner, and a 3-time All-Star, none of which were in a Padres’ uniform. After accumulating a 37-48 record in the Padres’ minor league system, he was traded to the Indians in a three-team deal where the Padres received Ryan Ludwick.
7 San Francisco Giants: Sergio Romo
Not every perceived draft day ‘steal’ is a future Cy Young winner or League MVP who was drafted in the 5th or 6th round. So-called ‘steals’ could also come in the form of Sergio Romo, who has been selected to just one All-Star game and has had his struggles in the postseason.
Romo, however, had tallied up a 32-26 record with 86 saves for the Giants spanning his nine years in San Francisco. All he cost the Giants, was a 28th round pick.
6 Seattle Mariners: James Paxton
James Paxton has been at the Major league level with the Seattle Mariners for 6 seasons. Over that time Paxton has a 41-26 record and is averaging a strikeout per inning.
While Paxton has not obtained any individual awards or All-Star appearances yet, the future looks to hold nothing but success.
Not only will Paxton be a 4th round steal by the time his career is completed, he is a 'steal' because the Blue Jays used a 1st round selection on him the previous year.
5 St. Louis Cardinals: 2000 - Yadier Molina
Selecting a future first-ballot Hall of Famer with anything but the 1st selection overall would be considered a ‘steal’. The Cardinals, however, selected Yadier Molina out of Ladislao Martinez High School in Vega Alta, Puerto Rico in the 4th round of the 2000 MLB Amateur Draft.
Currently in his 15th season with the Cardinals, he just recently appeared in his 9th All-Star game to add to his already achieved accolades of 8 Gold Gloves, 4 Platinum Gloves, and a Silver Slugger Award.
4 Tampa Bay Rays: James Shields
Despite being 11 years after drafting him and six years after promoting him to the majors, the 2011 season saw James Shields pay dividends on being a 16th round pick in the 2000 MLB Amateur Draft as he was selected to his only All-Star game. During his seven years with the Rays, Shields would have an 87-73 record with a 3.52 ERA. In addition to his All-Star selection, his 11 complete games and 4 shutouts placed him 3rd in the Cy Young voting.
3 Texas Rangers: Ian Kinsler
The Rangers selecting Edwin Encarnacion in the 9th round in 2000 was a steal, but he was traded to the Reds before putting on a Rangers uniform. Enter, Ian Kinsler, who has played in 1,066 games with Texas and started all but 8 of them.
Kinsler was drafted in the 17th round and is now a 4-time All-Star and a Gold Glove winner.
The Diamondbacks having drafted him in 2000 and 2001, just makes him an even bigger steal for Texas.
2 Toronto Blue Jays: Eric Thames
It needs to be stated that the Blue Jays biggest draft day ‘steal’ happened in 2010 when they drafted Kris Bryant in the 18th round. As most expected, Bryant chose to play baseball at the college level, which might have been why he artificially slipped to the Blue Jays. Two years previously, the Blue Jays did sign their 7th round selection Eric Thames. Thames would hit just 15 home runs over two seasons, half as many as he would hit for the Brewers in 2017.
1 Washington Nationals: Cliff Lee
The biggest draft day ‘steal’ since 2000 in the Washington Nationals’ franchise history, was actually made by the Montreal Expos, something that franchise was known for. In 2000 the Expos were able to achieve what the Marlins could not do in 1997, or the Orioles in 1998 and sign Cliff Lee. The Expos drafted Lee in the 4th round, but after 2 years in their minor system, they traded him to Cleveland. Lee would become a 4-time All-Star and win a Cy Young on his way to 143 career wins.