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10 Memorable MLB Draft Steals of the Past 25 Years

10 Memorable MLB Draft Steals of the Past 25 Years

The Cubs found one of the great hidden gems of this century when they drafted Josh Donaldson 48th overall in 2007.

The MLB draft has by far the lowest profile of any of the big three professional drafts because of the low immediate stakes. College players take years to reach the majors, and high schoolers take even longer.

There have been plenty of No. 1 overall picks who became superstars, such as Gerrit Cole, Bryce Harper, and Alex Rodriguez. But recent years have also produced historic numbers of busts, including Brady Aiken, Mark Appel, and Mickey Moniak. There's a reason most fans haven't heard of those latter three players.

Still, for teams picking outside of the top 20 in Sunday's 2021 MLB Draft, there are plenty of hidden gems to be found. Just look at Josh Donaldson, who slid to the Cubs at the end of the first round in 2007 as a catcher out of Auburn. Chicago never expected him to become a future MVP at third base, but he's become one of the best hitters of the last decade and landed a deal worth up to $100 million in free agency.

There are plenty of steals late in the draft — think Mookie Betts in the fifth round or Albert Pujols in the 13th — but few teams expected them to be stars, let alone major league contributors. If teams thought that, they would have gone far higher in the draft. In this list, we're going to focus on players on every team's radar in the first two rounds that just slipped through the cracks.

Here is a look back at 10 of the best steals in the last two-plus decades, plus who the teams ahead of them chose instead.

1998: CC Sabathia (20th overall)

The Indians made Sabathia a first-round pick as a lanky high school lefty, and he quickly reached the majors in 2001 as the youngest player in the league. Since then, there's little he hasn't done with the most WAR among pitchers (66.5) other than Justin Verlander. He won a Cy Young Award in 2007 and won a World Series with the Yankees after signing a record $161 million contract.

Sabathia has been incredibly durable with no trips to the injured list in his first decade in the majors and career totals of 251 wins and 3,093 strikeouts. His six All-Star appearances undersell his dominance. With the usage of starters decreasing over time, those figures should be enough to send him to the Hall of Fame when he first appears on the 2025 ballot.

Three Players Drafted Ahead of Him:

Brad Lidge, Seth Etherton, and Tony Torcato

Lidge is the only of these players to play more than 50 major league games. A two-time All-Star, his 221 saves from 2004 to '10 were sixth in baseball. He struck out an impressive 799 hitters in 603.1 innings and finished fourth in the Cy Young voting in 2008. Etherton, meanwhile, held a career 6.30 ERA in 23 starts, and Torcato recorded just two extra-base hits in 53 career plate appearances.

Best Player Drafted Ahead of Him:

J.D. Drew, 5th overall

Drew never lived up to the billing of a player selected twice in the top five (2nd in 1997 and 5th in '99), but he did launch 242 home runs over 14 major league seasons. He won a World Series with the Red Sox in 2007, made an All-Star game the year after that, and finished sixth in the 2004 MVP voting when he racked up 8.6 WAR. Thanks to underappreciated skills like strong right field defense and a career .384 OBP, he quietly accumulated 46.0 WAR.

2000: Adam Wainwright (29th overall)

The Braves nabbed Wainwright at the end of the first round in 2000 but traded him to the Cardinals three years later with Jason Marquis to land J.D. Drew. Drew went on to produce 8.6 WAR in his lone, yet highly productive, season in Atlanta, but Wainwright has nearly quintupled that total during his tenure in St. Louis.

Despite battling injuries and holding ERAs above 4.00 each season since 2016, Wainwright has a 3.39 ERA in 410 games (343 starts) over his storied career. From 2006 to '15, he held a 2.97 ERA and had four top-three Cy Young Award finishes. Wainwright was a World Series hero as the team's closer in 2006 and figures to have his No. 50 retired at Busch Stadium even if he falls short of the Hall of Fame.

Three Players Drafted Ahead of Him:

Corey Smith, Rob Stiehl, and Dave Parrish

None of the six players drafted directly ahead of Wainwright reached the majors, and two of them didn't make it above A-ball. Perhaps the most notable one of this group was Smith, who briefly appeared on Baseball America's Top 100 Prospects list at No. 73 in 2002 after hitting 18 home runs in the South Atlantic League. Although he never made the majors, he did rack up 172 homers and 1,351 hits over 12 minor league seasons.

Best Player Drafted Ahead of Him:

Chase Utley, 15th overall

With all due respect to Robinson Cano, Chase Utley has been the best second baseman of the 2000s thanks to outstanding defense and a strong offensive profile (.275/.358/.465). He has a solid case to be a Hall of Famer when he's first eligible to be on the ballot in 2024 after six All-Star appearances and a World Series title. Utley's 259 homers rank eighth all-time at the keystone position, while his 62.9 WAR rank 12th.

2002: Joey Votto (44th overall)

Although he doesn't have the power numbers of many of his contemporaries — he's only hit 30 home runs twice — Votto has undoubtedly been one of the most valuable players in the league since the Reds selected him at the top of the second round in 2002. He's one of 10 players this decade to have a wOBA of at least .400 thanks to incredible on-base skills.

Votto's impressive first four whole seasons, which included an MVP award, two All-Star appearances, and a second-place Rookie of the Year finish, earned him a 10-year, $225 million contract, which was the fourth-largest in MLB history at the time. He has followed that up with four more All-Star berths and five more top-10 MVP finishes and has led the league in OBP seven times.

Three Players Drafted Ahead of Him:

Micah Schilling, Blair Johnson, and Jason Pridie

Schilling and Johnson never made the majors, while Pridie briefly carved a niche for himself as a fourth outfielder with the Twins. In 133 games, he had a career .641 OPS, which is more than 100 points lower than Votto's career-worst mark last season (.768).

Best Player Drafted Ahead of Him:

Zack Greinke, 6th overall

Greinke is another surefire Hall of Famer with 15 straight years of dominance and an outside shot at 300 wins. Not only does he have dominant numbers with a 3.38 ERA and 3.97 K/BB ratio, but he's also the second-best hitting pitcher of the century after Carlos Zambrano. With a .225/.263/.337 line, he's has generated an extra 5.7 WAR at the plate. It's a shame he hasn't had a chance to hit much in Houston, although he will hit free agency when his then-record $206.5 million contract expires after 2021.

2004: Dustin Pedroia (65th overall)

Pedroia's lack of longevity will likely keep him out of the Hall of Fame, but the second baseman's star shined bright when he was (hopping) on the infield dirt in Boston. After a disastrous cup of coffee at 22, Pedroia ripped off eight straight seasons with at least 3.0 WAR, highlighted by a Rookie of the Year performance in 2007 and MVP season in '08.

The undersized second baseman was always an excellent defender and a .300 hitter from his first full season until his final at-bats. Knee injuries have held him to just nine games from 2018-19, during which his 3-for-31 performance at the plate has dropped his career average to .2993. Unfortunately, those have put an early end to a historic career and kept him from boosting his average even a fraction of a point before his 2021 retirement.

Three Players Drafted Ahead of Him:

Jason Jaramillo, Erik Corder, and Hunter Pence

Both Jaramillo and Cordier produced a negative WAR in their brief major league stints, but Pence accumulated the third-most WAR (31.1) among players drafted ahead of Pedroia. Pence has 244 career homers with a .279/.334/.461 slash line and had a career resurgence in 2019 with his fourth All-Star appearance at 36.

Best Player Drafted Ahead of Him:

Justin Verlander, 2nd overall

Verlander may well be the best pitcher of the century with two Cy Young Awards, an MVP, a Rookie of the Year Award, and three no-hitters. And he's seemingly still getting better. The 38-year-old has been lights-out since coming to Houston with a 2.45 ERA and 640 strikeouts in 477 innings. He led the league in WHIP and K/BB ratio in 2018 and 19 but missed all but one start in 2020-21 due to Tommy John surgery.

2007: Josh Donaldson (48th overall)

You can't blame the Cubs for not believing that Donaldson would become a star; the Athletics didn't think they had one for a while, either. After Chicago dealt the then-catcher to Oakland as part of a trade for Rich Harden, he debuted in 2010 but didn't play his first full season until 2013. But he made his presence known at age 27 with a 7.3-WAR season that earned him a fourth-place MVP finish and followed that up with four more seasons of at least 5.0 WAR.

From 2013 to '17, Donaldson was second only to Mike Trout with 34.4 WAR and sat sixth with 164 homers. An injury-filled 2018 forced him to take a one-year, $23 million deal with the Braves, but he signed a four-year, $92 million contract to join Minnesota. The Hall of Fame will be a long shot with such a late start to his career, but with an MVP award already under his belt, Donaldson has been one of the true first-round steals of the century.

Three Players Drafted Ahead of Him:

Justin Jackson, Drew Cumberland, Nathan Vineyard

None of the three players drafted directly before Donaldson made the majors, and you have to go 14 picks earlier to find a player who produced 20+ WAR (Todd Frazier, 23.8). Nationals closer Sean Doolittle (10.3, 41st pick) is the only player in double-digits.

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Best Player Drafted Ahead of Him:

David Price, 1st overall

It can be hard to live up to the sky-high expectations of being the No. 1 overall pick, but Price has done that and then some, narrowly edging Madison Bumgarner and Jason Heyward in this draft class. Although he had a poor reputation in the playoffs, he was key to Boston's 2018 title and Tampa Bay's '08 run, and he has five All-Star appearances, a Cy Young Award, and 217 million reasons to be happy about how his career has turned out.

2009: Mike Trout (25th overall)

What more is there to say about Trout? Not only is he the best player in baseball today, but he may also be the greatest of all time. Trout already had more WAR (73.4) in eight-plus seasons than either Derek Jeter and Reggie Jackson did in their Hall of Fame careers, and he has seven of the 14 best individual seasons by WAR since his debut in 2012.

Hindsight is 20-20, but it's wild that 24 other players went ahead of him in the draft. Some of that may have to do with him playing high school in New Jersey, where cold winters limit how much exposure prep players get. Billy Rowell (9th overall, 2006) was a recent bust not too far from Millville, where Trout calls home, and may have scared teams off from taking another risk. The Angels can thank Mark Teixeira for the 25th pick, as the Yankees forfeited their first-round selection to the Angels after signing the All-Star first baseman in free agency.

Three Players Drafted Ahead of Him:

Kyle Gibson, Jared Miller, Randal Grichuk

Gibson has developed into a solid mid-rotation starter and just made his first All-Star game in 2021, the final season of his three-year, $28 million contract in his first turn in free agency. But the more interesting comparison is to Grichuk, whom the Angels selected one pick ahead of Trout as compensation for losing closer Francisco Rodriguez. He hasn't become an All-Star, and his .295 career OBP leaves much to be desired, but Grichuk does have 150 career home runs in 817 games and hit a career-high 31 in 2019, which helped him land a $52 million extension with the Blue Jays.

Best Player Drafted Ahead of Him:

Stephen Strasburg, 1st overall

Few players have received as much buzz out of college as Strasburg, and he has been worth the hype after earning a record $15.1 million deal out of San Diego State. Although injuries have prevented him from crossing the 200-inning threshold more than twice, he has a dominant 3.21 ERA and 28.9 percent career strikeout rate. Fresh off of being named World Series MVP, Strasburg was able to set another record when he re-signed with Washington for $245 million over seven years. It was the largest deal ever for a pitcher until Gerrit Cole smashed that total two days later (nine years, $324 million), with some help from the Yankees.

2010: Christian Yelich (25th overall)

Yelich became one of baseball's top 50 prospects within two years of the Marlins drafting him in the first round in 2010, and he emerged as a defensive-minded, high-average hitter right away. With a small power surge in 2016 and '17, he compiled 16.4 WAR in his first four full seasons and looked to be a borderline All-Star for years to come.

But the January 2018 trade to the Brewers has fully unlocked his potential as he found his power stroke with 80 home runs in two seasons after totaling 59 in his first four-plus seasons. Yelich won the 2018 MVP and was a knee injury away from winning it again in '19. He doesn't turn 30 until December and figures to be one of the league's top all-around players for years to come.

Three Players Drafted Ahead of Him:

Kolbrin Vitek, Alex Wimmers, and Kellin Deglan

Vitek only lasted four years in the minors with the Red Sox before retiring at 24, while Deglan is still hoping for his first major-league appearance at 29. Wimmmers made 22 relief appearances with the Twins after being named National Pitcher of the Year at Ohio State, but he had nearly as many walks (19) as strikeouts (21).

Best Player Drafted Ahead of Him:

Chris Sale, 13th overall

This was a loaded draft class with Bryce Harper, Jameson Taillon, and Manny Machado going 1-2-3, but Sale narrowly has had the most sustained success of the group. His streak of seven straight All-Star appearances and top-six Cy Young Award finishes finally came to an end in 2019 when injuries limited his effectiveness. Despite that, he holds a career 3.03 ERA and is one of seven pitchers this century to register at least 300 strikeouts in a season. His 5.37 K/BB ratio is currently the all-time record.

2011: Trevor Story (45th overall)

The Rockies were able to buy Story out of his LSU commitment with a $915,000 bonus, and he immediately showed he was worth it. Story quickly made Colorado fans forget about Troy Tulowitzki when he homered twice in his major league debut and became the first player in MLB history to homer seven times in a team's first six games.

Story has continued to hit for power with 123 bombs in his first four seasons, but he's also become a complete player with impressive defense (17 DRS in 2019, 9th in baseball), sneaky speed (81 steals since 2018, 7th), and fewer strikeouts (21.3 percent, down from 31.3 percent his rookie season). The 29-year-old is one of the most complete players in the game today and figures to cash in big when he hits free agency this winter.

Three Players Drafted Ahead of Him:

Jeff Ames, Andrew Chafin, Michael Fulmer

Fulmer is the best of the group after taking home the 2016 AL Rookie of the Year Award for registering a 3.06 ERA in 26 starts. But he was far less effective in 2017 and '18 (4.21 ERA), missed all of 2019 due to Tommy John surgery, held an 8.78 ERA in 2020, and shifted into a bullpen role in 2021. Chafin has developed into a solid reliever but only produced 1.1 WAR in his career-best season (2019), while Ames only made three appearances in Triple-A.

Best Player Drafted Ahead of Him:

Francisco Lindor, 8th overall

Story may be one of the most complete players, but Lindor can stake his claim as the best shortstop in the game. Before the shortened 2020 season, he was the only player to ever record 40 doubles and 30 homers in three straight seasons and adds incredible defense to his outstanding offensive profile. He signed a 10-year, $341 million extension, the third-largest deal in baseball history, with the Mets after coming over in a trade from Cleveland.

2013: Aaron Judge (32nd overall)

The Yankees can thank Nick Swisher's departure for the arrival of one of the game's greatest power hitters. After Swisher signed with the Indians as a free agent, the Yankees got a compensatory pick that they used on a massive slugger out of Fresno State. Scouts were nervous about his ability to consistently make contact, but that has not been an issue, as he has made up for his career 30.46 percent strikeout rate with massive walk numbers (15.2 percent) and even more power.

Judge set a rookie record with 52 homers, which has since been surpassed by Pete Alonso (thanks in part to the juiced baseball). His health has been problematic, but Judge crushes the ball when he's on the field, and more than a third of his fly balls have gone for homers since 2017, by far the best mark in baseball.

Three Players Drafted Ahead of Him:

Ryne Stanek, Travis Demeritte, and Jason Hursh

Hursh and Demeritte never amounted to much in the Braves' system, and Stanek may be a run-of-the-mill reliever, but he did start one of the biggest revolutions in baseball. He ushered in the age of the opener with the Rays, starting 56 games over the past two years and holding a 2.71 ERA with 102 strikeouts in 83 innings. He is a factor at the back of Astros' bullpen this season thanks to his upper-90s heat.

Best Player Drafted Ahead of Him:

Kris Bryant, 2nd overall

An injury-shortened 2018 aside, Bryant has been as good as advertised with a Rookie of the Year campaign in 2015 and a 39-homer MVP season the following year. With the versatility to play all three outfield positions as well as a solid third base, he is one of the game's great young stars. Still only 29, Bryant figures to cash in on an Anthony Rendon-sized contract soon when he hits free agency this winter.

2014: Matt Chapman (25th overall)

Chapman may not be as recognizable as several other stars on this list, but he's been far better than the Athletics could have hoped when they snagged him at the end of the first round out of Cal State Fullerton. He's finished in the top 10 for Defensive Runs Saved in each of his three seasons and paced baseball with 29 DRS in 2018 when nobody else eclipsed 21.

In addition to the fine glove, Chapman broke out with 36 home runs in 2019, all while maintaining a smaller-than-average strikeout rate. He's never had a high average but makes up for it with good plate discipline (10.2 percent walk rate) and is one of six players to reach 6.0 WAR each of the last two full seasons.

Three Players Drafted Ahead of Him:

Grant Holmes, Derek Hill, and Cole Tucker

There's still time for each of these players to develop, but none have Chapman's upside. Tucker debuted at 22 in 2019 but has only hit .213/.259/.320 for the Pirates with solid defense at shortstop and center field. Hill debuted at 24 in 2020 but has just a .200/.310/.200 line in 29 plate appearances. Holmes has spent 2021 in Triple-A but figure to contribute only has a reliever.

Best Player Drafted Ahead of Him:

Aaron Nola, 7th overall

Trea Turner may give Chapman a run for his money as the best hitter of the class, but Nola has the edge on the mound. The LSU product finished third in the Cy Young voting in 2018 and has a career 3.58 ERA with 1,048 strikeouts to just 281 walks in 944 innings. Just 28, he's an ace in the making if he's not already there.