Ranking the 10 Best Late-Round MLB Draft Steals Since 2000

Though some of the guys listed here are perhaps the biggest steals of all, I decided to trim the first five rounds of the draft -- coincidentally the only rounds of the 2020 draft -- off of the criteria that determined “late-round” eligibility. That doesn’t mean I’m not going to recognize the fact that Mike Trout was selected 25th overall in 2009, after several less-impressive players. There were 24 of them, to be exact, by virtue of Trout’s stranglehold on the top player since 2010. Two outfielders taken before Trout that year -- Donavan Tate (3rd overall) and Jared Mitchell (23rd overall) -- never played in a big league game.

Here are some players who went within the first five rounds, but unlike Trout, were taken toward what will be the end of the 2020 draft.

- Cliff Lee (Fourth Round)
- Yadier Molina (Fourth Round)
- Mookie Betts (Fifth Round)
- Ryan Howard (Fifth Round)
- Max Muncy (Fifth Round)
- Jeff Samardzija (Fifth Round)

The Expos took Martin in the 35th round of the 2000 MLB Draft, but Martin pushed his professional career to a later date in order to further develop his skills. He attended Chipola College, where he was ironically teammates with another member of this top 10 list. A note to any prospects looking to attend college instead of signing with a team that drafted you: Chipola might be a good landing spot. Head coach Jeff Johnson has seen 17 young players develop into Major League talents during his 22-year reign.

Two years later, Martin signed with the Dodgers after the organization expended a 17th round pick on the catcher (though he was originally listed as a second baseman). The Canadian backstop made his debut four years later and blossomed into a star immediately, finishing in the top 10 in Rookie of the Year voting and earning his first All-Star selection in the following season. Since 2000, only Buster Posey and Yadier Molina have posted a higher WAR than Martin among all catchers, and Martin has never posted a negative offensive or defensive WAR.

Four all-star selections combine with a Gold Glove award and Silver Slugger award to make him an amazing 17th-round value.

The 2005 MLB Draft was a good one for future outfielders, as Andrew McCutchen, Brett Gardner and Jacoby Ellsbury were all All-Stars (McCutchen, an MVP). However, this was relatively expected of them, as they were all taken within the first three rounds.

Michael Brantley, who was selected by Milwaukee in the seventh round, currently trails these three outfielders in the WAR statistic but is also arguably the guy who has the most fuel left in the tank. He’s coming off of three straight All-Star seasons and saw his 2019 play reach a point that was comparable to his MVP-caliber 2014 campaign. Of the four players in question, Brantley has the best batting average at .297 and is second with a .792 OPS, trailing McCutchen’s .858 figure.

There were 23 outfielders selected before Brantley in 2005 that never stepped foot in a big league game. And though the Brewers may wish they had held on to him in hindsight, they were looking to make a competitive playoff push at the time, which is why they included him as a “player to be named later” in a deal with the Indians that netted them CC Sabathia.

Of outfielders selected in the 2004 draft, Hunter Pence may have the more complete career so far between him and Cain. But in the WAR department, thanks to strong defensive play, Cain can hold the objective title of the most valuable outfielder from that year’s crop of prospects. Even crazier is that Pence was a second-round pick, while Cain went 15 rounds later.

Described in his draft profile as a “younger version of Preston Wilson,” he never quite developed the pop that Wilson had. But in almost every other aspect, Cain is the superior player, with a 36.1 WAR compared to Wilson’s 6.4. A two-time All-Star, Cain was instrumental in the Royals’ 2015 World Series run, picking up at least five hits in each of the three playoff series and adding onto his postseason legacy, which already included a 2014 ALCS MVP award.

Bautista is the aforementioned teammate of Russell Martin at Chipola, but unlike Martin, it took Bautista a little while to get going once he made it to the bigs. The Pirates’ 20th-round selection had a tumultuous start to his career, becoming a Rule 5 selection by the Orioles after spending years in the Pirates’ farm system. He was then picked up by the Rays off the waivers from the Orioles, then bought out by the Royals, then traded to the Mets, and then sent back to Pittsburgh… all in one year.

Even in his return to Pittsburgh, he was nothing special, struggling to hit for much power and hovering around a .240 batting average for his whole stay. They had seen enough by 2008, trading him north of the border to Toronto. Even then Bautista wasn’t doing much. At 28, he spent the majority of his first season in Toronto posting the same numbers that Pirates fans had grown tired of seeing.

I’m not entirely sure what happened at the end 2009, but something clicked. He hit 10 home runs and posted a .944 OPS over 30 games in September and October. A sign of things to come, Bautista’s power surge continued into 2010, and into 2011, and kept going all the way until 2015. He was an All-Star for six consecutive seasons, a span in which he averaged 38 home runs and 97 RBI per game and became one of the most fearsome sluggers in the league.

Not bad for an afterthought in the 20th round and a late-blooming journeyman.

Similarly to his former Blue Jays teammate, Encarnacion was drafted later than his stats would indicate and it took him a while to get going. The Rangers drafted him as a third baseman but traded him to the Reds just one year later, perhaps because they already had a developing slugger awaiting his chance, in Hank Blalock. He developed in Cincinnati and was underwhelming in the bigs, though his power was slightly more potent than Bautista’s.

And then, as if Bautista’s Toronto success had unlocked some secret formula for bringing out the best in older sluggers, Encarnacion broke out in a big way in the 2012 season. He swatted 42 home runs to form a dangerous one-two punch with Joey Bats, and followed up 2012 with his first All-Star appearance in 2013. Since 2012, he has yet to hit fewer than 32 home runs in a season. No player in baseball has hit more home runs than Encarnacion (297) since 2012, and without any strong indication that there will be a drop off in his production, he’s a legitimate candidate for 500 home runs.

Though the sixth round may not be a “late round” of the draft, it’s still a place where you’ll see a significant decline in MLB production. In fact, Rizzo is the only player drafted in the sixth round of the 2007 draft that has actually made an MLB impact. Joe Mahoney, Scott Maine and Ryan Brasier are the only other guys in that sample that ever made it to the bigs.

Rizzo was selected by the Red Sox but was traded a few years later as a big chip in Boston’s trade package for Adrian Gonzalez. Rizzo was coming off a 25-homer, 100-RBI season in various levels of the minors, and he continued that strong display in his first minor league season in the Padres’ system. However, he was extremely underwhelming in his call up, batting .141 in 128 at bats with just one home run.

San Diego moved him to Chicago, where he developed a little bit more and had another fine minor league showing (23 HR, .342 batting average) before making the jump up to the Majors. He hasn’t been anywhere but the bigs since that final call up, nabbing three All-Star nominations and finishing in the top 20 in MVP voting in five straight years from 2014 to 2018.

He’s been the model of consistency and leadership for the Cubs, and at only 30 years old, he has time to build upon his already-impressive resume.

Martinez opted to attend Nova Southeastern University in Florida instead of starting his big league career with the Twins out of high school. It was the Astros that took him in the 20th round the second time around, and he was solid in an irregular role for a few years in Houston. When he went to Detroit as a free agent in 2014 -- he was released by the Astros the same year -- he proved his past team wrong and developed a reputation as a fearsome slugger right off the bat. His .912 OPS in his first year as a Tiger trailed only Victor Martinez (and beat Miguel Cabrera) for the team-high, and he was named an All-Star the following season.

A batter like Martinez is a rarity in the majors, capable of pure power and clean hitting, as indicated by his age-30 season in 2018. He delivered in his first year with the Red Sox in a big way, clubbing 43 home runs, leading the league with 130 RBI, and posting a slash line of .330/.402/.629. His 2019 season was also worthy of an All-Star nomination, and when all of this is weighed with the fact that he was not a top-five, nor a top-10, nor a top-15, but a top-20 pick, you realize just how big a steal he was.

The Diamondbacks had their eyes on Kinsler, drafting him in 2000 before he decided to attend Central Arizona College. He absolutely dominated as a freshman, prompting the D-Backs to take him yet again in the 2001 draft. Yet again, Kinsler declined and transferred to Arizona State. It wasn’t until his next transfer, this time to Mizzou, that he felt he had developed enough to make the step up to professional baseball. But it was the Rangers, not the Diamondbacks, who selected him in 2003.

Once Kinsler was called up to the majors, the second baseman found an everyday role and never let go, making four All-Star teams in seven seasons. Since 1980, there are only six second basemen with a better WAR than Kinsler, and he’s in the top five at the position in home runs and runs scored. A true five-tool threat, which is especially valuable at a position like second base, Kinsler provided first-round value for the Rangers and Tigers before retiring after the 2019 season.

Goldy’s decision to continue his development in college is what allowed the Diamondbacks to secure their all-time greatest hitter three years after his initial selection in the draft. A six-time All-Star, Goldschmidt proved scouts wrong and is the guy that Pete Alonso, Rhys Hoskins, and others can thank when they’re given high prospect rankings. J.J. Cooper of Baseball America says that because of Goldschmidt’s dominance, scouts and analysts are “more inclined to give extremely productive first basemen some benefit of the doubt” if their athleticism isn’t off the charts.

I don’t blame Cooper. Goldy’s a four-time Silver Slugger and a three-time Gold Glove winner who has hit for power, hit for average, gotten on base, stolen bases (32 in 2016), defended well and provided leadership. You couldn’t ask for much else from a first overall pick, much less an eighth round selection.

There are only 21 pitchers in MLB history who have won multiple Cy Young awards. Many of them, like Roy Halladay, Roger Clemens, Randy Johnson, Greg Maddux, and even Tim Lincecum, were first- or second-round picks. There’s also a ninth-round pick in that exclusive club, and he has done enough to capture the top spot on this list.

deGrom, a converted shortstop, was labeled a solid prospect with some good action on his pitches, but nothing was said that indicated he’d rise to where he is now. In fact, an upgrade to his initial Baseball America report said that his development in the Mets’ farm system added that he could become “a potential No. 3 or 4 starter,” (via John Sheridan of Metsmerized). I think it's safe to say that he's surpassed that estimation.

He probably has a few more Cy Young awards left in him, as well, considering he’s been named the winner the past two seasons and is showing no signs of slowing down. In 2018, he led the league with a 1.70 ERA. In 2019, he led the league with 255 strikeouts. He rarely lets up home runs. His strikeout to walk ratio is consistently among the league leaders. He's cool as a cucumber in close, low-scoring games, and he's a part of way too many for his own good.

If his career continues on its current trajectory, we could be talking about the top MLB draft pitching steal of all time.