Even in the best of times, baseball’s amateur draft is loaded with uncertainty. And these most certainly are not the best of times.
The coronavirus pandemic has wiped out months of amateur competition, meaning scouts have less information to go on, and Major League Baseball is preparing to slash this year’s draft to just five rounds. That means less opportunity to gather quantity over quality. The Red Sox’s upcoming draft class has been further eroded by sign-stealing penalties that took away their second-round pick.
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That’s all to say, this draft might be one for the history books, but perhaps not one for the record books.
So, instead of looking ahead, let’s look back by digging through the Baseball-Reference archives for the best-ever Red Sox draft picks in each round. Because the first-round tends to be lopsided, we’ve broken it into sections – high, low and somewhere in the middle – but every other round is limited to one pick (with a few ties sprinkled throughout). And if you assumed this exercise would be easy, just fast-forward to the fifth round, where the choice comes down to the two best right fielders in franchise history.
MORE: We built the best 3 lineups you can make from Red Sox draft picks
High first round – Trot Nixon (No. 7), 1993, 21.2 WAR
The Red Sox had a top-five pick in each of the first three amateur drafts, and they selected Billy Conigliaro and Ken Brett – two perfectly good big-league players whose brothers, Tony and George, respectively, happened to be far more successful – and then Mike Garman, an Idaho high school player who eventually pitched nine years in the big leagues but only 20 games for the Red Sox.
They haven’t had a top-five pick since.
Since 1967, the Red Sox have picked higher than 12th only three times, and each of those was the seventh-overall selection. Nixon is so far the best of the bunch, but Andrew Benintendi (the 2015 pick) is on pace to surpass him. The only miss in this group has been 2013’s Trey Ball, a high school lefty who tried to convert to the outfield and became a free agent this winter.
Mid-first round – Roger Clemens (No. 19), 1983, 139.2 WAR
The Red Sox also drafted a Hall of Famer (Jim Rice) and a one-time franchise icon (Nomar Garciaparra) in the middle of the first round, but the selection of Clemens at No. 19 overall stands out. He is the single greatest drafted player in franchise history.
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“I was completely surprised (to be drafted by the Red Sox),” Clemens once told Peter Gammons. “As far as I was concerned, Boston was a foreign country.”
Clemens spent almost half of his career in Boston, winning three AL Cy Young awards and generating 80.8 WAR, third-most in franchise history behind Ted Williams and Carl Yastrzemski (each of whom preceded the draft).
Late first round – Mo Vaughn (No. 23), 1989, 27.1 WAR
This was not the best Red Sox pick in 1989 – spoiler alert: skip ahead to the fourth round – but at No. 23 overall, Vaughn is the best they’ve ever done at the end of the first round. Bruce Hurst and Jacoby Ellsbury generated slightly higher career WAR totals from nearly identical draft slots, but Vaughn had more success in Boston, including an MVP award.
January first round – Carlton Fisk (No. 4), 1967, 68.4 WAR
For 21 years, Major League Baseball had a secondary draft every January. Its impact was far more limited than the June draft, but it did generate the greatest catcher in Red Sox history. Fisk was the fourth overall selection in 1967, truly the best top-of-the-draft pick in team history.
How limited was the January draft otherwise? Despite running for more than two decades, there’s a chance you remember only two other Red Sox January picks: Curt Schilling in 1986 and Ellis Burks in 1983. The next-best might be occasional starter Chuck Rainey.
Supplemental first round – Three-way tie: Jed Lowrie (2005, 17.0 WAR), Clay Buchholz (2005, 16.7 WAR), Jackie Bradley Jr. (2011, 15.9 WAR)
With these three, it’s hard to single out one over the other. Their career WAR totals are within 1.1 of one another, and if there’s any sort of 2020 season, Bradley Jr. will likely surpass both Lowrie and Buchholz as the best. So, take your pick: Lowrie has had perhaps the best career (but much of it came outside of Boston), and Buchholz had the best peak (but injuries took their toll). And Bradley Jr. has the highest Red Sox WAR (but more than a third of it came in a single standout season).
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Second round – Tie: Curt Schilling (1986, 79.5 WAR), Dustin Pedroia (2004, 51.6 WAR)
If we’re counting only the June draft, then it’s a nearly impossible choice between Dustin Pedroia and Fred Lynn, with Jon Lester in the conversation as well. We’ll give Pedroia the nod because he’s spent his entire career in Boston. He was also the lowest selection of the bunch at No. 65 overall (of the 64 players drafted ahead of him in 2004, only Justin Verlander has had a better career).
But that’s only counting the June draft.
The final January draft was held in 1986, and the Red Sox’s second-round pick was Schilling, who might very well be voted into the Hall of Fame next winter. Although he spent most of his career elsewhere – 17.7 WAR with the Red Sox – Schilling did win two World Series in Boston and deliver perhaps the most famous performance for arguably the most beloved Red Sox team in history.
Third round – Mike Greenwell, 1982, 25.8 WAR
Tino Martinez was the Red Sox’s third-round pick in 1985 and went on to slightly outperform Greenwell, but Martinez didn’t sign until the Mariners took him in the first round three years later.
Without Martinez, Greenwell is an easy choice here, with nearly double the career WAR of the next-best selection: 1968 pick Lynn McGlothen.
Fourth round – Jeff Bagwell, 1989, 79.9 WAR
One-hundred percent of Bagwell’s big-league career happened in Houston, and his Red Sox impact is limited to the regrettable 1990 trade for reliever Larry Anderson, who pitched 22 innings for a team that ultimately was swept in the ALCS. So, most impactful fourth-round pick to actually play for the Red Sox? That’s most definitely Jonathan Papelbon, the championship closer taken with the 114th pick in 2003. But getting a Hall of Famer at No. 110 overall is pretty hard to beat (though the Red Sox actually have done better later).
Fifth round – Tie: Dwight Evans (1969, 67.1 WAR), Mookie Betts (2011, 41.8 WAR),
Please don’t make us choose. The two greatest right fielders in Red Sox history were each fifth-round draft picks. Evans spent 19 years with the Red Sox, building a career that might one day end up in Cooperstown. Betts played five and a half years for the Red Sox and was on pace to easily top Evans’ career WAR total before he was traded this spring.
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One key difference between the two: Evans was pick No. 109 overall. In Betts’ draft year, that would have been in the middle of the third round. Betts was No. 172 overall. In Evans’ year, that would have been in the eighth round. Greatest fifth-round impact for the Red Sox might be Evans, but the best fifth-round pick was probably Betts.
Underrated Red Sox fifth-round success: Amos Otis in the inaugural 1965 draft.
Sixth round – Tie: Cecil Cooper (1968, 36.0 WAR), Anthony Rizzo (2007, 33.5 WAR)
Two similar players stand out. Both became All-Star first basem*n for playoff teams in other cities. Cooper did actually have some impact in Boston (.772 OPS through parts of six years) before being traded to the Brewers for Bernie Carbo and George Scott. Rizzo never played in Boston before he was shipped to San Diego for Adrian Gonzalez, but he gets bonus points for being selected all the way down at No. 204 overall, 76 spots lower than Cooper.
Seventh round – Wade Boggs, 1976, 91.4 WAR
For almost a decade now, we’ve marveled at the Red Sox selection of Betts as a fifth-rounder in 2011. But long before Betts went 172 overall, the Red Sox found their greatest mid-round value in Boggs at No. 166. He wound up being the second-best player in a Cooperstown-heavy draft, falling behind Rickey Henderson and ahead of Alan Trammell and Jack Morris (Ozzie Smith was also drafted in the seventh round that year, though he didn’t sign). No other Red Sox seventh-rounder is even vaguely in the conversation. The Red Sox did draft eventual Astros All-Star Glenn Davis in the seventh-round of the 1980 January draft, but he didn’t sign.
Eighth round – Kevin Youkilis, 2001, 32.4 WAR
It seems the Red Sox have loaded up on corner infielders in the sixth, seventh and eighth rounds. Youkilis is the clear standout among eighth-rounders, though. That round’s been pretty good for the Red Sox – Jody Reed, Tim Naehring, Justin Duchscherer, Al Nipper, Brandon Moss, Jeff Sellers – but Youkilis has by far the best career numbers of the bunch. He was the best Red Sox pick of the entire 2001 draft and wound up playing a key role for the 2007 championship team.
Ninth round – Travis Shaw, 2011, 9.4 WAR
If Mark Teixeira had signed in 1998, he would be easily the team’s best ninth-round selection. But he didn’t, so the choice is down to two current players (both, oddly enough, picked exactly No. 292 overall). The choice here is Shaw, who had a pair of 30-homer seasons in Milwaukee after an uneven stint in Boston. The alternative is Christian Vazquez, who followed four relatively underwhelming seasons with a breakout in 2019. For now, Shaw has the better career, but Vazquez could supplant him (and Vazquez has a ring).
10th round – Brady Anderson, 1985, 35 WAR
Anderson made his big-league debut with the Red Sox in April 1988, but just a few months later, he was included with Schilling in a trade for Mike Boddicker. Anderson would go on to hit 210 home runs, most of them with the Orioles, including an outlier 1996 season when he hit 50 and finished ninth in MVP voting.
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11th round – Ben Oglivie, 1968, 26.4 WAR
Separated by 32 years, the Red Sox found a pair of three-time All-Stars in the 11th round, but both were traded before they could play roles on two iconic Red Sox teams.
The first was Oglivie, who became an All-Star and home run champion in Milwaukee after the Red Sox traded him in October 1973, two years before their World Series matchup against the Big Red Machine. The second was Freddy Sanchez, the Red Sox’s most successful draft pick in 2000 who was traded in July 2003 – if he’d stuck around one more year, he would have earned a World Series ring – and went on to lead the National League in hitting with the Pirates.
12th round – Lew Ford, 1999, 8.3 WAR
Traded a year later for Hector Carrasco, Ford became a fairly well-regarded prospect with the Twins and carved out a six-year career mostly as a part-timer, with one standout season in 2004. If not Ford, the Red Sox’s best 11th-rounder is either 1980s outfielder Reid Nichols or 2018 trade bait Jalen Beeks, who went to the Rays and brought back Nathan Eovaldi.
13th round – Carl Pavano, 1994, 16.4 WAR
Dustin Pedroia has always made an outsized impact, even for his draft slot. (Matthew Thomas / Boston Red Sox)
The only Red Sox 13th-rounder to generate more than 1.1 WAR in his career, Pavano’s greatest impact came as the prospect traded for Pedro Martinez in 1997. Just for fun, Pavano went on to beat the Yankees in the 2003 World Series – he was dominant in Game 4 for the Marlins – then signed a $39.95 million deal with the Yankees, for whom he was both injured and bad. Does that make him the greatest Red Sox player to never play a game for them?
14th round – Dana LeVangie, 1991, 0 major-league games
He never played a game in the majors and was a .196 hitter as a minor-league catcher, but drafting LeVangie in 1991 is what got him into the Red Sox system and started a career that’s spanned every role from scout to bullpen catcher to championship pitching coach. That has to be the best use of a 14th-round pick in franchise history. Don’t believe me? Only two players drafted and signed by the Red Sox in the 14th round have even made it to the majors, and of those two, only one has a positive career WAR: It’s little-used left-handed reliever Bobby Poyner. Draft stock really thins out beyond the first 10 rounds or so.
15th round – Ernie Whitt, 1972, 18.3 WAR
Lost to the Blue Jays in the 1976 expansion draft, Whitt went on to have a good career as Toronto’s primary catcher throughout the ’80s, highlighted by an All-Star appearance in 1985.
16th round – Oil Can Boyd, 1980, 17.3 WAR
Like Whitt, Boyd is the standout of this round by a large margin. He was a Red Sox rotation mainstay through much of the 1980s and finished with a 4.04 career ERA. Next-best in the round? Lefty reliever Erik Plantenberg, who never pitched for the Sox and rarely pitched for anyone else.
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17th round – Josh Reddick, 2006, 25.4 WAR
Josh Reddick’s real impact came elsewhere, but he was still an impressive 17th-round pick (Stephen Brashear / Getty Images)
The top picks for rounds 12 through 15 only highlight what a great selection Reddick turned out to be. Drafted out of a Georgia junior college, he’s put together an 11-year career with a Gold Glove and a World Series ring. Traded for Ryan Sweeney and Andrew Bailey at the end of the 2011 season, Reddick, now 33, is still going strong as a .273 career hitter with 140 career home runs.
That 2006 17th round was a pretty good one, by the way, also producing nine-year vet Tony Watson and 12-year man David Robertson.
18th round – Ron Mahay, 1991, 7.9 WAR
Drafted as an outfielder in 1991, recruited as a strike replacement player in 1995 and converted to a pitcher in 1996, Mahay wound up pitching 14 years in the major leagues as a left-handed specialist. He and Hunter Strickland each had lasting big-league relief careers as Red Sox 18th-round picks. They are objectively the best of the Red Sox’s 18th-rounders, though around The Athletic, we subjectively prefer now-colleague Lars Anderson, the first baseman-turned-writer who played 30 games for the Red Sox from 2010 to 2012.
19th round – David Eckstein, 1997, 20.9 WAR
In 2000, the Red Sox needed a roster spot for Lou Merloni. They opened it by designating Eckstein for assignment. He was claimed by the Angels, finished fourth in AL Rookie of the Year voting the following season, then finished 11th in MVP voting the year after that. In his career, Eckstein was selected for two All-Star teams and won two World Series. Oops. Great pick, though.
20th to 24th round – Bill Lee, 22nd round in 1968, 22.0 WAR
As the rounds get into the 20s, the availability and history of impact players fade considerably. The Red Sox have drafted and signed only one 21st-round pick who reached the majors – journeyman reliever Joel Bennett – and they have yet to graduate a 24th-rounder to the big leagues (though Jantzen Witte is making a case).
Pitchers Tom Bolton (20th round, 3.4 WAR) and Mike Paxton (23rd, 2.3 WAR) had meaningful big-league careers, but they pale in comparison to Lee.
It took one year for the Spaceman to go from the 507th pick to becoming a member of the Red Sox’s major-league staff. He pitched mostly out of the bullpen for four years before making the All-Star team as a starter in 1973. He wound up pitching 284 2/3 innings that season (a full 200 1/3 innings more than he’d thrown the year before), the start of a six-year run when he averaged 26 starts with a 3.68 ERA.
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25th to 29th round – John Flaherty, 25th round in 1988, 1.6 WAR
By WAR, pitchers Mark Bomback, Pete Ladd and Kason Gabbard rank a little higher, but it’s hard to look past Flaherty’s 14-year career, remarkable for such a low-round pick. The Red Sox have drafted only five major leaguers in the 25th round, and this one managed to catch 1,032 major-league games. Great pick.
The Red Sox got 26th-rounder Mauricio Dubon in 2013, and he was used to trade for Tyler Thornburg (and now has a chance to stick as a utility man with the Giants), but he and Flaherty are exceptions this late in the draft. It would be a different story if Yasmani Grandal (27th round, 2007) or Alex Bregman (29th round, 2012) had actually signed.
30th round and later – Dan Giese, 34th round in 1999, 0.5 WAR
Now the Yankees director of professional scouting, Giese languished in the minor leagues for nine seasons – and even briefly retired at one point – before making his big-league debut at age 30. He ultimately pitched in 35 games with a 4.22 ERA across three major-league seasons, and he’s an easy choice for the best-ever Sox pick after the 30th round.
According to Baseball-Reference, only six others who signed with the Red Sox after such a late selection ever made it to the major leagues, including 36th rounder Trevor Kelley, who debuted last season. Many picks this late simply refuse to sign, including Red Sox selections Pat Burrell, Hunter Renfroe, Mike Yastrzemski, Ricky Romero and Yan Gomes, who all re-entered the draft pool years later and had big-league impacts with other teams.
The latest the Red Sox have ever drafted and signed a major leaguer was Dennis Tankersley in the 38th round of the 1998 draft. He was pick No. 1,135, the Red Sox had drafted him two years in a row, and he went on to pitch in 27 games for the Padres. The Red Sox traded him for one month of Ed Sprague.
(Top photo of Mike Greenwell: Focus on Sport / Getty Images)
