The List: The Best First-Off-The-Board High School Pitchers

High school pitchers are risky propositions in the draft, but the full extent of their risk profile—even for the first prep lefthander and righthander selected—is startling.

Nevertheless, the return on investment for that rare high school pitcher who stands above his peers on draft day, then remains healthy and fulfills his potential can be immense. Here are nine examples of successful prep pitchers in the common draft era—1987 to present—who were either the first lefthander or first righthander selected in their class. That distinction is important because going off the board first signifies esteem by the industry.

1. Clayton Kershaw • lhp
2006 draft (seventh overall)
Highland Park HS, University Park, Texas

The 18-year-old Kershaw wasn’t so much about projection as he was raw stuff, which included a killer breaking ball and a mid-90s fastball that was regarded as the finest in the prep ranks in 2006. The Dodgers made Kershaw, already 6-foot-4 and 220 pounds, the first high school pitcher selected in his draft class, and though the draft that year featured a surfeit of quality first-round arms, including collegians Max Scherzer, Tim Lincecum, Ian Kennedy and Andrew Miller, the prep southpaw from the Dallas suburbs developed into a generational talent who already owns three National League Cy Young Award trophies.

2. C.C. Sabathia • lhp
1998 draft (20th overall)
Vallejo (Calif.) HS

Sabathia did not turn 18 until July of his draft year of 1998, but even at that juncture, he faced questions about his weight, which was listed as 240 pounds on a 6-foot-7 frame. His blazing fastball up to 97 mph and feel for secondary pitches ultimately won the day, and Sabathia rewarded the Indians with eight seasons of excellence, including an American League Cy Young Award in 2007. Though Sabathia remained on the board until the 20th pick in 1998—the only prep pitcher to go higher was righthander J.M. Gold to the Brewers at No. 13—he returned more value than any first-rounder in his class.

3. Josh Beckett • rhp
1999 draft (second overall)
Spring (Texas) HS

No high school righthander ever has gone No. 1 overall in the draft, and despite the demographic’s sheer volume, just eight have gone No. 2 overall, including Beckett to the Marlins in 1999 and, more recently, Jameson Taillon (2010) and Tyler Kolek (2014). Just three of the eight No. 2’s have forged successful careers (so far): J.R. Richard (1969), Bill Gullickson (1977) and Beckett, who nearly redeems the group by himself. He topped out at 98 mph with a killer breaking ball as a 19-year-old senior in 1999 and then shined brightest at the biggest moments of his career, serving as staff ace for World Series-champion 2003 Marlins and 2007 Red Sox.

4. Madison Bumgarner • lhp
2007 draft (10th overall)
South Caldwell HS, Hudson, N.C.

Three college lefthanders (David Price, Daniel Moskos and Ross Detwiler) went off the board before the Giants made Bumgarner the first prep southpaw taken in 2007. Teams liked Bumgarner’s low-90s velocity as a 17-year-old high school senior, but they didn’t know quite how to project his low three-quarters arm slot and lack of a changeup. Those turned out to be non-factors, for one could argue that Bumgarner has outperformed fellow 2007 first-rounders Price and Jason Heyward, especially when considering his 2.14 ERA and 0.88 WHIP recorded in 88 October innings for the World Series-champion Giants of 2010, 2012 and 2014.

5. Kerry Wood • rhp
1995 draft (fourth overall)
Grand Prairie (Texas) HS

A classic high school power pitcher with mid-90s heat and a knee-buckling curveball, Wood flew through the minors and rose to national prominence with a 20-strikeout one-hitter for the Cubs on May 6, 1998. Tommy John surgery wiped out his 1999 season, but Wood recovered to serve as co-ace along with Mark Prior for the 2003 Cubs team that advanced to the National League Championship Series. A string of injuries truncated his career as a starter—he last started 20 games in a season at age 27—but he continued as a reliever until retiring in 2012 at age 34. In retrospect, Wood outperformed every first-rounder in his draft class except Roy Halladay and Todd Helton.

6. Jon Garland • rhp
1997 draft (10th overall)
Kennedy HS, Granada Hills, Calif.

Garland won 136 games in a 13-year big league career, recording a 4.37 ERA (103 ERA+) in 2,151 innings. He turned in a perfectly fine career, yet outside of his excellent 2005 season (and postseason) for the World Series-champion White Sox, Garland feels like a mild disappointment based on his pedigree as the first prep righthander selected in his class. (The Cubs drafted him as a projectable 17-year-old, but then traded him across town a year later for reliever Matt Karchner.) The first round of the 1997 draft yielded Lance Berkman, J.D. Drew (unsigned) and Troy Glaus, but the pitching class underwhelmed in pro ball, with Garland returning far more value than the college arms taken ahead of him (Matt Anderson, Jason Grilli, Dan Reichert).

7. John Danks • lhp
2003 draft (ninth overall)
Round Rock (Texas) HS

Danks rose to prominence as a high school senior when he hit 94 mph and began to sit in the low 90s, which enticed the Rangers to make the Austin-area southpaw the top prep pitcher drafted in 2003. He comfortably outperformed the collegians who went off the board ahead of him (Kyle Sleeth, Tim Stauffer, Paul Maholm), though not before Texas traded Danks, then at Triple-A, to the White Sox after the 2006 season (for Brandon McCarthy). Danks burned brightly in Chicago for five seasons—he ranked seventh among lefties with 20 WAR from 2007 to 2011—before recording a 4.92 ERA (80 ERA+) from 2012 until his May release.

8. Gavin Floyd • rhp
2001 draft (fourth overall)
Mount Saint Joseph HS, Baltimore

“Scouts say Floyd is as safe as a high school pitcher can be,” we wrote in the Maryland prep’s 2001 draft scouting report. The scouts were half right about the 6-foot-4 Floyd, who showed low-90s heat and a power curveball as an amateur. Selected fourth overall by the Phillies, Floyd ran up a 6.96 ERA in parts of three seasons and 109 innings for Philadelphia, and he wasn’t much more effective at Triple-A. Traded to the White Sox after the 2006 season (for Freddy Garcia), Floyd blossomed into a reliable mid-rotation arm in Chicago—just like Jon Garland and John Danks did. While overshadowed by 2001 first-rounders Mark Teixeira, Joe Mauer and Mark Prior, Floyd actually returned far more career value than any first-round prep pitcher in his class.

9. Steve Avery • lhp
1988 draft (third overall)
Kennedy HS, Taylor, Mich.

Drafted by the Braves in 1988, Avery finished 1989 with 13 starts at Double-A, then made 13 more starts at Triple-A in 1990 before making his big league debut at age 20. Avery shined for the dynastic Braves teams of the early 1990s, recording a 3.17 ERA (122 ERA+), while averaging 243 innings per season (including the playoffs) from 1991 to 1993. A heavy workload might have caught up to Avery beginning in 1994—when he was still just 24—for he recorded a 4.40 ERA (97 ERA+) for the Braves from that season until 1996. Avery was effectively done by 1999, when he made 19 starts as a 29-year-old for the Reds.

Nevertheless, Avery returned more career value than any first-round high school pitcher from his draft class, but he ranks distinctly behind collegians Andy Benes, Charles Nagy and Jim Abbott.

Who’s Next?

Might someone in the minors now help to redeem the ranks of first high school lefthander or righthander drafted?

The best bet would appear to be Pirates righthander Jameson Taillon (2010 draft, second overall), who despite missing all of 2014 and 2015, has pitched well at Triple-A Indianapolis this season. The 24-year-old has gone 3-2, 1.82 through eight starts, with 9.3 strikeouts and 0.9 walks per nine innings. He has allowed just two home runs.

The other hopeful would be Braves lefthander Kolby Allard (2015 draft, 14th overall), who currently is in extended spring training as he awaits his 2016 assignment. He ranked No. 84 on the Top 100 Prospects list this spring.