Beyond Round 5: The Best Later-Round Draftees, Part 1

On Wednesday and Thursday, Major League Baseball will hold a drastically abbreviated version of its annual amateur draft. As part of the pandemic-related agreement the players and owners hashed out in late March, this year’s draft will be just five rounds. With the contraction of the minor leagues looming, it’s quite likely that future drafts will be considerably more abridged than the 40 rounds they’ve been since 2012, if not necessarily this short.

Had such conditions been in effect prior to this year, numerous quality major league players would have gone undrafted. While some might have still developed after being signed as free agents, it’s entirely likely that many would have slipped through the cracks, never making a dent in the professional ranks, let alone reaching and thriving in the majors.

What follows here and in Part 2 tomorrow is a round-by-round look at the best players drafted in each round beyond the fifth since the amateur draft was instituted in 1965. With the database help of Ben Clemens, we’ve assembled top-five WAR rankings for rounds six through 25, and I’ve attempted to summarize the career highlights of each player in concise fashion (hat-tip to Baseball America’s Ultimate Draft Book for some of the tidbits on why draftees slipped to later rounds). Additionally, I’ve highlighted one active player who may or may not have cracked the leaderboard yet, but who’s noteworthy, as well as two Hall of Fame relievers who didn’t make their respective leaderboards.

6th Round

A four-time All-Star and three-time top four finisher in the MVP voting, Bando manned the hot corner for the A’s during their mid-1970s dynasty and ranks 16th at the position in JAWS, with a stronger seven-year peak (44.4 bWAR) than the average Hall of Fame third baseman (43.1). Hudson, a four-time All-Star and three-time finisher among the top four in the Cy Young voting was part of the “big three” of the Moneyball-era A’s and a key rotation member for seven playoff teams. The seemingly ageless Moyer didn’t click with the Cubs — who four rounds earlier had drafted Greg Maddux — but pitched in the majors until age 49 and served as a rotation staple for four postseason teams, including the 2008 champion Phillies. Zobrist redefined the term “utilityman,” serving as a multiposition regular for eight playoff teams and three champions, most notably winning World Series MVP honors with the 2016 Cubs. Burkett earned spots on two All-Star teams and made postseason starts for the Rangers, Braves, and Red Sox.

Notable active player: Anthony Rizzo (2007 Red Sox, 29.2 WAR). Traded twice early in his career, Rizzo joined Zobrist on that drought-busting Cubs team. As the Cubs’ first baseman, he’s made three All-Star teams and won three Gold Gloves while reaching 4.0 WAR in five of the past six years.

7th Round

With 3,010 hits, five batting titles, 12 All-Star appearances, and a lifetime .328/.415/.443 line, Boggs was an easy first-ballot Hall of Fame selection in 2005. Edmonds, an acrobatic eight-time Gold Glove-winning center fielder who helped the Cardinals to two pennants and a championship, went one-and-done on the 2016 BBWAA ballot but ranks 15th in JAWS at the position. Likewise, Randolph, a six-time All-Star who started for five pennant winners, ranks 16th among second basemen in JAWS. Holliday was a seven-time All-Star who thumped 314 home runs while helping the Rockies and Cardinals reach the postseason a total of nine times; he was the 2007 NLCS MVP when Colorado won its first pennant. The well-traveled Sanders played for seven teams in seven seasons from 1998-2004, starting for four of them, three of which (the 2001 Diamondbacks, ’02 Giants, and ’04 Cardinals) at least reached the World Series.

Notable active player: Justin Turner (2006 Reds, 26.0 WAR). Turner additionally passed through the hands of the Orioles and Mets before emerging as a centerpiece of the Dodgers’ lineup as they rolled to six straight NL West titles. He took home 2017 NLCS MVP honors while helping the team to its first World Series in 29 years.

8th Round

Though Burnett could be frustratingly erratic at times — he walked nine Padres and hit another in his May 12, 2001 no-hitter for the Marlins — the quality of his stuff was such that he struck out at least 195 batters in a season five times. Lowe struggled at times as well, but made the AL All-Star team both as a starter and a closer, and rebounded from a regular season 5.42 ERA in 2004 by becoming the first pitcher to start the Division Series, League Championship Series, and World Series clinchers in the same October while helping the Red Sox break “The Curse of the Bambino.” Radke helped the Twins to four AL Central titles from 2002-06 while serving as a model for the organization’s pitch-to-contact style. Schmidt made three All-Star teams and was a key member of the 2002 NL champion Giants’ rotation.

Notable active player: Goldschmidt. A three-time top-three finisher in the NL MVP voting as a Diamondback, he made six straight All-Star teams from 2013-18 while ranking fourth in the majors in WAR during that span. His first year as a Cardinal wasn’t as impressive, but he’ll likely remain a force to be reckoned with and should top this list within a couple of years.

9th Round

Though only one of this round’s leaders was actually chosen by Toronto, the whole slate has a very Blue Jays flavor. Barfield (1985), McGriff (’89), and Encarnación (2015-16) all played significant roles on playoff-bound Toronto teams, while Leibrandt (’85 Royals) and Alexander (’87 Tigers) played key roles in thwarting those efforts. McGriff was traded to the Blue Jays just 18 months after being drafted. While he may not be loved by JAWS or BBWAA voters, his 493 home runs might well carry the five-time All-Star to Cooperstown via this winter’s Today’s Game Era Committee voting. Barfield was regarded as having the strongest arm of any outfielder of his time, and is second in B-Ref’s fielding runs among right fielders (161), trailing only Roberto Clemente. Encarnación, who earned the unenviable nickname “E5” for his struggles at third base, fared much better upon becoming a DH/first baseman, and has clubbed 414 homers thus far; his 297 since the start of the 2012 season is tops in the majors. The lefty-throwing Leibrandt played the grizzled rotation veteran role with the World Series-winning Royals as well as the pennant-winning 1991 and ’92 Braves.

Alexander was part of the most bountiful draft crop in major league history, as the Dodgers also grabbed Bobby Valentine (first round), Bill Buckner (second), Tom Paciorek (fifth), and Joe Ferguson (eighth) in the main draft, plus Steve Garvey (first) and Ron Cey (third) in the June secondary phase. Alexander played just one year for the Dodgers, starting a 19-year career that covered nine teams. He was traded from the Braves to the Tigers on August 12, 1987 for prospect John Smoltz, then went 9-0 with a 1.53 ERA in 11 turns for a team that took advantage of the Jays’ season-ending 0-7 flop.

Notable Hall of Famer: Rich Gossage (1970 White Sox, 31.1 WAR). The archetype of the fire-breathing, flame-throwing reliever, “Goose” predated the one-inning closer model; his 193 saves of four outs or more (out of 310 total) ranks second only to Rollie Fingers. In a career spanning from 1972-94, he struck out at least 100 batters in a season out of the bullpen five times (tied with Fingers and Dellin Betances for the lead), made nine All-Star teams, and pitched for three pennant-winners, including the 1978 World Series-winning Yankees.

Notable active player: Jacob deGrom (2010 Mets, 31.5 WAR). Just missing the cut on the leaderboard is the player who inspired this series. The lanky righty didn’t reach the majors until age 26, but won NL Rookie of the Year honors in 2014, came up huge during the ’15 postseason while helping the Mets reach the World Series, and has taken home back-to-back Cy Young awards in the past two seasons. As noted recently, his numbers for his first six seasons are a ringer for those of Clayton Kershaw.

10th Round

Remembered mainly for his 50-homer breakout in 1996 — he topped 20 homers just two other times in 15 years — Anderson was a three-time All-Star who played center field for the Orioles’ 1996 and ’97 teams, which made it as far as the ALCS. Byrd is among a select group of players to hit a home run for 10 different franchises. Sweeney, a five-time All-Star, was a bright spot during some very dark seasons with the Royals; only once during his 1995-2007 run did the team crack .500. Hammel rounded out the rotations of six playoff-bound teams including the 2016 Cubs, even if he was often a bystander come October.

Notable active player: Kendrick. Considered a third- or fourth-round talent, Kendrick slipped to the 10th; as told in Eric Longenhagen and Kiley McDaniel’s Future Value, scout Tom Kotchman played the pursuit of the St. Johns River Community College second baseman so quietly that no other teams scouted him. The pinnacle of Kendrick’s solid 14-year career with the Angels, Dodgers, Phillies and Nationals came during last year’s postseason, when he went on a run for the ages. His 10th-inning grand slam off the Dodgers’ Joe Kelly was the difference-maker in the Division Series clincher, and after earning NLCS MVP honors against the Cardinals, his seventh-inning homer off the Astros’ Will Harris turned Game 7 of the World Series in the Nationals’ favor.

11th round

At Florida A&M, Dawson went relatively unnoticed, and was mainly known for his defense. As it turns out, he brought a tremendous combination of speed and power to the majors, with five seasons of at least 20 homers and 20 steals at the start of a 21-year career that eventually earned him a spot in the Hall of Fame. Pitching alongside a Hall of Fame trio, Millwood helped the Braves to four straight playoff appearances from 1999-2002, threw a full no-hitter for the Phillies on April 27, 2003, and the first six innings of a combined no-hitter for the Mariners on June 8, 2012. Davis, the first Jamaica-born player to reach the majors, made three All-Star teams and retired with the number three ranking in home runs (350) among switch hitters, though he’s since been bumped down to seventh. Drabek won the 1990 NL Cy Young with the Pirates, for whom he served as the staff ace during their run of three straight NL East titles. Cirillo made a pair of All-Star teams and hit for a .320 batting average or higher four times, only one of which came with the Rockies.

Notable Hall of Famer: Trevor Hoffman (1989 Reds, 25.9 WAR). Drafted as a shortstop out of the University of Arizona, Hoffman switched to pitching in his third pro season, and spent his entire career (1,035 games) in the bullpen. He made seven All-Star teams, and held the career saves record from 2006-11.

Notable active player: Joc Pederson (2010 Dodgers, 13.1 WAR). Pederson has totaled 123 homers in his five-plus seasons for the Dodgers, four of them worth 2.7 WAR or more. His light-tower power turned many heads in the 2015 and ’19 All-Star Home Run Derbies.

12th Round

Of the five draft-era pitchers with at least 100 WAR, Ryan — who dealt triple-digit heat and set records for strikeouts (5,714), walks (2,795), and no-hitters (seven) that are likely unbreakable — is the only one drafted after the third round. Retrosheet, Baseball-Reference, the aforementioned Baseball America book, and other resources consider him to have been drafted in the 12th round, but that 1965 draft — the first of its kind — was more complicated than that, according to The Athletic’s Jake Kaplan and Tim Britton, citing MLB.com’s Jim Callis. Long story short, Ryan was the Mets’ 12th selection, but some teams had as many as 22 chances to draft him because rounds eight onward included multiple picks per team, based upon the number of A-level affiliates they had:

“It was definitely a goofy system that makes no intuitive sense. But it’s wrong (to say Ryan was a 12th-round pick). Nolan Ryan was a 10th-round pick,” Callis said. “You can’t say the 12th pick by the Mets was a 12th-rounder because there were teams that had two picks each round and some teams had five.”

Via The Athletic, the average team passed on Ryan 15 times. All of which is to say that while I’m happy to acknowledge that this is an unholy mess to untangle, I’m sticking with the popular notion of Ryan in the 12th round and moving on. The young fireballer went unpicked in part because he had “the worst day of his life” — getting overworked by his coach after a bout of wildness, and pitching on short rest — the day Mets crosschecker Bing Devine saw him, but he was still on the board when they took him with the 295th pick, not that they were able to use him to full advantage before trading him and three other players to the Angels for Jim Fregosi on December 10, 1971.

Smiley, a two-time All-Star, was the number two starter behind Drabek on the Pirates’ 1990 and ’91 NL East champs, and later helped the Reds to the ’95 playoffs. Ray spent nine of his 10 seasons (1981-90) as the starting second baseman for the Pirates and Angels, missing out on each team’s postseason trips but making his lone All-Star team at age 31. Caldwell was pitching for the Brewers, his fourth team, by the time he broke out for a 22-9, 2.36 ERA season that made him the runner-up to Ron Guidry in the 1978 AL Cy Young race; he also pitched for Milwaukee’s ’82 pennant winners, spinning a three-hit shutout in the World Series opener against St. Louis and collecting the win in Game 5 as well. Pineiro was a pitcher of considerable promise and exceptional stuff, but shoulder and elbow injuries limited him to just four seasons with over 25 starts.

Notable active player: Robbie Ray (2010 Nationals, 12.2 WAR). Traded twice since being drafted, Ray helped the Diamondbacks to a Wild Card berth in 2017, making his first All-Star team along the way. In his five full seasons, he’s reached 200 strikeouts three times; among lefties, only Chris Sale has done so more often.

13th Round

Born in the Dominican Republic, Pujols and family first moved to New York City and then Independence, Missouri. A three-time MVP and two-time World Series champion, he’s in the company of Hank Aaron, Willie Mays, and Alex Rodriguez as the only players with at least 3,000 hits and 600 homers, and he’s second among first basemen in JAWS despite his latter-day struggles with the Angels. He’ll be the second Hall of Fame first baseman drafted in this round after Thome, who was actually drafted as a skinny 6-foot-4 shortstop, and went homerless in his first professional season. He went on to slug 612 home runs, including a record 13 walk-off shots, while powering 10 teams to the postseason.

Clark was a heavy hitter in his day, clubbing 340 home runs while serving as the muscle on the speed-driven 1985 and ’87 Cardinals pennant winners; he fell to the 13th round because most teams viewed him as a pitcher. Finley’s defensive metrics don’t exactly match up with his six Gold Gloves, but he hit 304 homers and started for the 1998 NL pennant-winning Padres and 2001 World Series-winning Diamondbacks. Dykstra’s post-career problems have overshadowed how good a table-setter he was, particularly for the 1986 Mets and ’93 Phillies.

Notable active player: Matt Carpenter (2009 Cardinals, 29.9 WAR). Carpenter missed most of two seasons at Texas Christian University due to Tommy John surgery, and signed for just a $1,000 bonus. The versatile lefty swinger has helped the Cardinals to five playoff berths and made three All-Star teams while spending seasons as the Cardinals’ regular first, second, and third baseman.

14th Round

A knee injury suffered while playing football, concerns about his ability to hit the ball in the air, and a history of clashing with coaches caused Parker to slip to the 14th round, and he signed for just a $6,000 bonus, but he certainly panned out. From 1975-79, he tied for fourth in the majors with 30.3 WAR; during that span he won a pair of batting titles, an NL MVP award, an All-Star MVP award (those throws!) and a World Series. While he made a total of seven All-Star teams and hit 339 homers in a career that spanned 1973-91, he’s remembered as much for what might have been given drugs, injuries, and a defensive decline.

Kison, a wiry, feisty righty who was known for his willingness to pitch inside, played key roles on the Pirates’ 1971 and ’79 champions. Molina, one of three brothers with long major league careers as catchers, wasn’t much of a hitter but was an elite pitch framer whose skills were brought to the forefront thanks to the analytics movement. Easler, a teammate of Parker and Kison on those 1979 Pirates, had a few big seasons with the bat in a 14-year career scattered across six teams.

Notable active player: Fowler. Though he was committed to Miami University, the Rockies were able to sign Fowler by offering him a $925,000 bonus, 10% of what they saved by trading Larry Walker to the Cardinals that summer. While Fowler himself has scuffled lately with the Cardinals, he earned All-Star honors with the Cubs in 2016 while serving as their center fielder and leadoff hitter. Most notably, he homered off Corey Kluber to lead off Game 7 of the World Series, the one in which the Cubs ended their 108-year championship drought.

15th Round

This one has a decidedly West Coast flavor. Peavy made two All-Star teams and won the 2007 NL Cy Young as a Padre, then pitched in the rotations of championship-winning Red Sox and Giants teams. Canseco, notorious for his steroid-related exposé Juiced, was the AL Rookie of the year in 1986 and the MVP in ’88, when he became the first player to combine 40 homers and 40 steals in a season; he helped the A’s to three straight pennants from 1988-90. Murphy, a six-time Gold Glove-winning center fielder, started for the 1981 A’s, the franchise’s lone playoff team between the 1972-74 and ’88-90 dynasties. Dempsey, who lasted 24 seasons as a defense-minded backstop, was the unlikely MVP of the 1983 World Series with the Orioles and made key contributions to the Dodgers’ 1988 run, including catching the World Series clincher. Mueller spent six of his 11 years with the Giants plus one with the Dodgers, though the pinnacle of his career came with the 2003-04 Red Sox; he was the AL batting champion in ’03, and went 6-for-14 in the ’04 World Series, that after famously driving in Dave Roberts with the game-tying run in Game 4 of the ALCS agains the Yankees and Mariano Rivera.

Notable active player: Shane Greene (2009 Yankees, 4.2 WAR). Few recent 15th-round picks have made much impact at the major league level, though Greene, who was selected out of Daytona Beach Community College and later dealt in a three-way deal that involved Robbie Ray and Didi Gregorius, has produced some bright moments as a closer, most notably making the AL All-Star team for the Tigers in 2019 before being traded to the NL East-winning Braves.