The Boston Red Sox Draft History

The Boston Red Sox have found some amazing players over the 50-plus years in the MLB First Year Player Draft. They’ve also had their fair share of misses as any team will have, there are no guarantees in the draft after all. With the Rule 4 Draft just a day away, Scott Maxwell looks at the Boston Red Sox draft history to see how the team has faired over the first half-century of the amateur draft.

Since the amateur draft began in 1965, the fortunes of franchises have been shaped by the selections they have made. While free agency, both amateur and international, plays a larger role in team building than it did when the draft was instituted, the acquisition of young, cost-controlled talent through the draft remains invaluable.

Until 1987 the player selection process included the traditional Rule 4 Draft in June, a secondary June draft, and two lesser January drafts. (There was yet another draft, in August, that was done away with after 1966.) Talent was nearly impossible to find in all but the June amateur draft, which was by far the largest. Fortunately, baseball streamlined the draft to a single, annual event.

Over the history of the draft, the Red Sox, like most teams, had far more misses than hits. However, the hits helped make for some of the greatest teams in franchise history.


In 1965, newly-appointed General Manager Dick O’Connell selected outfielder Billy Conigliaro, younger brother of Tony, as Boston’s first-ever draft choice and the fifth overall pick. Tony visited the Swampscott (Mass.) High graduation ceremony that day and made an announcement, “Ladies and gentlemen, I thought you might like to know that my brother, Billy, was the first draft choice of the Boston Red Sox”. Billy had no idea and was elated that the local team nabbed the consensus top-10 pick. Unfortunately, Billy never lived up to his brother’s promise as a hitter. His career got off to a good start for a few years in Boston, but he was traded to Milwaukee along with George Scott and Jim Lonborg for Tommy Harper and others in 1971. Billy was out of baseball by the end of the 1973 season.

The first draft was proof that high-end talent could be found throughout, with Hall of Famers Johnny Bench (second round), Tom Seaver (10th round) and Nolan Ryan (12th round) going after the first round. The remainder of the Red Sox first draft was largely forgettable aside from fifth-round pick Amos Otis.

Over the rest of the 1960s, Boston drafted a few players that impacted the franchise. The Red Sox selected Ken Brett in 1966, who was one of the more successful players in that year’s draft class. Brett was seen as a centerfielder by most clubs, but the Red Sox drafted him as a pitcher. One year after his selection, he became the youngest player ever to pitch in the World Series at 19-years-old.

The Red Sox kicked off the “Impossible Dream” year of 1967 by drafting Hall of Famer Carlton Fisk with the fourth choice in the usually talent-barren January draft. Fisk was described as a “strong-armed, speedy catcher” who came highly recommended by scout Jack Burns. Fisk made his Fenway debut two years later. In 1968, Cecil Cooper and Ben Oglivie joined the fold, and Bill Lee was a bargain with the team’s 22nd-round pick. Rick Miller (second round) and Dwight Evans (fifth round) capped the decade in the 1969 draft. Evans proved to be one of the best picks in franchise history. The White Sox also had their eye on Evans, and scout Joe Stephenson was impressed with his “plus throwing arm” and “fine eye and a good idea of the strike zone.”


The team finally hit a first-round home run in 1971 with the selection of Jim Rice. Drafting Rice also broke down some barriers. Will McDonough wrote the following day, “Black is finally beautiful with the Red Sox. After years of virtually ignoring black ballplayers as big league prospects, the Sox went the other way by taking two blacks—Jim ‘Ed’ Rice and Milton Jefferson—one-two in the free agent draft.” Rice was surprised he was drafted as high as he was, but the Red Sox had been scouting him for some time. The franchise was rewarded with a career that ended with a plaque in Cooperstown.

The next major addition was Fred Lynn. The New York Yankees selected Lynn in the 1970 draft, but he fortunately chose to attend USC instead. The Red Sox got another chance to draft Lynn in 1973 and took him in the second round. It was a bit of a gamble since Lynn had another year of college eligibility. “Sure, I’d love to sign with the Red Sox. If they make the right offer, I’ll go for it”, Lynn said after the draft. He took the Sox’ offer, and made an immediate impression. Just weeks after signing, Peter Gammons reported, “The Red Sox are extremely pleased with their second round draft choice in this June’s draft, Southern Cal left-handed outfielder Fred Lynn. He is at Bristol and has a 10-game hitting streak, is batting .370 with power (in the five games Ed Kenney saw, he hit four homers) and is a good outfielder.” Lynn was AL Rookie of the Year and MVP by 1975. The “Gold Dust Twins,” Rice and Lynn, were in the fold.

Although the team did draft some talent in the subsequent years, including Butch Hobson, Ed Jurak, Bob Stanley, and Dave Stapleton, the next major additions came in 1976. The Red Sox took lefty Bruce Hurst 22nd overall. Hurst was rated the fifth overall prospect going into the draft. Former Red Sox Frank Malzone, then a player development consultant, said that while he was “no Frank Tanana,” Hurst was “pretty good.” Indeed. Hurst and seventh-rounder Wade Boggs would make a significant impact on the franchise in the following decade.

Boggs was not highly regarded at the time of the draft. Kansas City Royals scout Tom Ferrick wrote that he “needs a lot of help with [the] bat” and that it would take $20,000-$25,000 to sign and he was “not worth that much.” The Red Sox followed the advice of scout George Digby and took a chance on him. Boggs is now in the Hall of Fame and his number was recently retired by the Red Sox. Apparently, the five-time batting champion and member of the 3,000-hit club did not need as much help with the bat as some originally thought. John Tudor, Glenn Hoffman, Reid Nichols, and Gary Allenson were also selected in 1976. It was a clearly successful draft that yielded several major leaguers, though the team regrettably drafted pitcher Larry Jones just ahead of Jack Morris and Rickey Henderson in the fourth round.

After lousy 1977 and 1978 drafts, the Red Sox infamously made catcher Marc Sullivan their second-round choice in the 1979 draft. Sullivan was the son of GM Haywood Sullivan, Haywood is best known for letting Luis Tiant, Fred Lynn, and Carlton Fisk leave via free agency. Marc knew the pick would raise eyebrows saying, “No one in their right mind would believe that they’d waste a high draft pick because of the father-son thing. But I guess there will be people for a while who’ll say I’m only here because of my dad. I’ll have to get used to and play my way out of it.” If by “it” he meant a wet paper bag, then he was unsuccessful. For his career, he hit five home runs and batted .186 in just 137 major league games. The decade ended with a whimper.


In 1980 the Red Sox missed early on, but unearthed some talent later in the draft with the selections of pitchers Dennis “Oil Can” Boyd and Al Nipper. Red Sox fans were introduced to Steve Lyons in the first round of the 1981 draft, and many current NESN viewers wish the team picked pretty much anyone else. Tony Gwynn or Frank Viola, drafted soon after, would have been icing on the cake.

The Rule 4 Draft of 1982 saw the Red Sox select slugger and “founding father” Sam Horn with the first of their three first-round selections. Horn and fellow first-rounder Jeff Ledbetter were compensation picks for the loss of the previously mentioned Tanana and Joe Rudi. A Dodgers scout called Horn “the second coming of Willie McCovey.” He fell far short of the comparison. The team enjoyed a little more success with third-round selection Mike Greenwell. Early in 1983, Boston was able to find a rare impact player in the January player with Ellis Burks

Heading into the 1983 draft, the Red Sox had failed to pick a true franchise player since 1976. As a result, the teams of the early 1980’s were largely forgettable. Boston finally landed a star in the first round in 1983 with the selection of Roger Clemens, who at the time of the draft was participating in the College World Series with the Texas Longhorns. Scouting director Eddie Kasko had Clemens ranked fifth on the team’s draft board and was surprised he made it to the Red Sox at number 19. Pawtucket Red Sox manager Joe Morgan predicted he “might come pretty quick.” Morgan was correct. Clemens started 20 games the following year and won the Cy Young in his third professional season. He, along with Boggs, would headline the mid-late 1980s teams that won the division three times. 1983 also marked the merciful end of Haywood Sullivan’s reign of terror.

New GM Lou Gorman chose catcher and future Olympic hero John Marzano 14th overall in 1984, passing on the likes of Greg Maddux and local southpaw Tom Glavine. The club selected Tino Martinez in the third round in 1985, but he did not sign. In its final January draft, in 1986, the team chose Curt Schilling. They also selected “All-Star” Scott Cooper that June.

In 1988, the Red Sox had another shot at Tino Martinez, but passed in order to take pitcher Tom Fischer in the first round. Martinez went two selections later to Seattle. The Sox did walk away with solid major league infielders John Valentin and Tim Naehring later in the draft.

The Red Sox once again had three first-round choices in 1989. Gorman finally hit on the second choice, nabbing first baseman Mo Vaughn of Seton Hall. He was a New England native, and he attended the Red Sox-Yankees game the night he was drafted. Vaughn said of his goals, “I don’t want to be a guy who hits a lot of home runs but just bats .220. I want to be a tough out. I want to be someone you have to make good pitches to to get out.” He succeeded. Vaughn led the club to the postseason during his 1995 MVP season and again in 1998 during the first year of the Pedro Martinez era. Jeff Bagwell was selected in the fourth round, and had Gorman not traded him for Larry Andersen the following season, 1989 would have been one of the more impactful drafts in franchise history.


Boston did not own a first-round pick again until 1991 when they chose pitcher Aaron Sele. In the following round, Moneyball hero – catcher Scott Hatteberg – was selected. The team bottomed out in 1992 with a record of 73-89, in no small part due to some shoddy work in previous drafts.

With the team’s highest pick since 1967, the Red Sox took outfielder Trot Nixon at seventh overall in the 1993 draft. Nixon was a two-sport star in high school and had signed a letter of intent to go to North Carolina State. Scouts saw him as having “all the tools and instincts” to be an impact player. He made it clear after the draft that, “I prefer to sign with the Red Sox if the negotiations go well.” Of course, he signed and, though he was not the elite talent he was projected to be, he was a significant contributor to the team for a number of years. The Sox also added pitcher Jeff Suppan and infielder Lou Merloni later in the draft. It turned out to be Gorman’s final draft as Dan Duquette took over GM duties after the 1993 season.

Duquette made a great first impression by drafting shortstop Nomar Garciaparra with the 12th overall pick in 1994. Garciaparra was coming off a monster season for Georgia Tech, hitting .431 with 12 home runs and 30 stolen bases. Garciaparra also fared well in the Cape Cod League that summer, batting .327 for Orleans. He had been drafted by the Brewers in 1991, but he chose to go to college instead. There wasn’t much of a question about his signability this time. He said, “Right now I just want to be part of a championship team (at Georgia Tech) and then join the Red Sox.” Like Clemens, Garciaparra was in the midst of the College World Series at the time of the draft. The Yellow Jackets, who also featured catcher Jason Varitek, made it to the title game but lost to Oklahoma. Later in the 1994 draft, Duquette landed infielder Donnie Sadler and pitchers Brian Rose and Carl Pavano. Pavano was a key piece used to acquire Pedro Martinez a few years later.

Duquette’s draft record was spottier in the second half of the 1990s. He took pitcher Andy Yount just ahead of Roy Halladay in the opening round of the 1995 draft. The team did add some minor talent in 1996 by taking Chris Reitsma, Dernell Stenson, Justin Duchscherer, and Shea Hillenbrand. Duquette followed that up with a less impressive 1997 draft. The only player of note was 19th-round selection David Eckstein.

The team tried to rediscover some first-round magic with another shortstop in 1998 with 12th overall pick Adam Everett. He did not match Garciaparra’s success. This draft is perhaps best known for ninth-round selection Mark Teixeira, who felt he was treated poorly by team officials and chose to go to Georgia Tech instead of taking $1.5 million from the Red Sox. He spurned the franchise again prior to the 2009 season as a free agent when negotiations went sour and he signed with the Yankees.

In 1999, Boston took pitcher Casey Fossum 48th overall. Duquette was also close to drafting Albert Pujols in the 10th round, but he was unable to ensure Pujols would sign on his terms and passed.


The 2000s were a time of change for the Boston Red Sox. When the club was sold in 2002 to John Henry’s ownership group, it marked the first time since 1933 that the club was not connected to the Yawkey family. Fenway Park went through substantial redevelopment, and the losing culture soon forever changed. Duquette was replaced by interim-GM Mike Port in 2002 and eventually by local kid Theo Epstein in 2003. Epstein’s vision of a “$100 million scouting and player-development machine” was also a striking departure from club history. Duquette’s final two drafts were largely forgettable, aside from 2001 eighth-round pick Kevin Youkilis.

The club’s new era started with a bang. With their first selection in the 2002 draft the Red Sox took high school lefty Jon Lester in the second round. However, much of the buzz the next day was not about Lester. Pitcher Jason Neighborgall, who was considered an elite talent and expected to demand a $5 million bonus, was drafted in the ninth round. He didn’t sign, but the Red Sox already had their future ace. Lester was slightly disappointed he slipped past his hometown Seattle Mariners, but he was anxious to get his professional career started. “Hopefully I’ll sign early and get down there and start pitching and start my career playing for the Red Sox. I’d rather sign than attend school,” he said. Lester received a $1 million bonus and quickly signed. He went on to pitch in two World Series for the club, including winning the clinching game of the 2007 Fall Classic.

Epstein’s first draft in 2003 was also a solid start. His picks included Jonathan Papelbon, David Murphy, Matt Murton, and Abe Alvarez. Future MVP second baseman Dustin Pedroia was taken in the second round in of the 2004 draft. Pedroia was a Golden Spikes Award finalist at Arizona State, and was expected to go higher in the draft. He likely slipped due to his stature at 5’9”, which also drew comparisons to former draft pick David Eckstein. The club was wavering between Pedroia and Kurt Suzuki. Both players were scouted by David Finley. Finley and regional cross-checker Dan Madsen both had Pedroia rated slightly higher, so the team selected the former. “The Red Sox are getting a player who’s going to play hard every day, loves to win, and whose main goal is to win a championship,” Pedroia said after the draft. Prophetic. Pedroia led the club to a championship in his rookie year and was AL MVP the next.

One of Epstein’s best drafts came in 2005. Jacoby Ellsbury, Clay Buchholz, Jed Lowrie, Craig Hansen, and Michael Bowden all contributed to the major league club. Hansen, a closer from St. John’s, was the center of attention post-draft due to the high cost agent Scott Boras was demanding. He ultimately signed for $4 million. After being rushed to the major-league level that same year, Hansen flamed out. Ellsbury drew easy comparisons to the Red Sox centerfielder at the time, Johnny Damon. It was fitting, since both Ellsbury and Damon eventually jumped ship to the Yankees in free agency. Ellsbury was the fastest player in the draft and was an on-base machine for Oregon State. Buchholz slipped due to character concerns. He had been dismissed from McNeese State’s baseball team after he stole 29 laptops from a middle school and sold them on campus. Scouting director Jason McLeod, now with the Cubs, felt those character issues were resolved, but Epstein disagreed. The two had an intense argument over the issue and Epstein nearly destroyed the draft board in a fit of anger. The team ultimately took Buchholz with the 42nd overall pick, and Red Sox fans have been throwing things in anger ever since. Despite the frustrations, taking Buchholz at that stage in the draft was a positive for the Red Sox.

The 2006 draft did not start out as well. Outfielder Jason Place never panned out and Daniel Bard’s career got off to a great start before he completely lost the ability to command his pitches. However, Theo did find pitcher Justin Masterson in the second round. In 2007, the eventual World Series winners chose third baseman Will Middlebrooks and first baseman Anthony Rizzo.

The Red Sox had some misfortune in the 2008 draft. Outfielder Ryan Westmoreland looked like a steal in the fifth round. He was rated the 21st overall prospect by Baseball America heading into the 2010 season and McLeod recently called him the most talented player he ever drafted. Tragedy struck when Westmoreland was diagnosed with a cavernous malformation in his brain stem that ultimately ended his career. Fortunately, it was not life threatening. Christian Vazquez, Casey Kelly, and Ryan Lavarnway were among the other players selected.

In 2009 had the club picked a mere three slots higher, they would have had the chance to draft Mike Trout. They had to settle for fellow centerfielder Reymond Fuentes instead. 2016 breakout outfielder Jeremy Hazelbaker was taken in the fourth round. Suffice it to say, the final draft of the decade was not their best.


The 2010s saw more change and upheaval. The Red Sox made two GM changes in a four-year span. The club went from World Series contenders to last place, then repeated that cycle once again. In 2010, the team lost Jason McLeod to Jed Hoyer’s Padres and Amiel Sawdaye took over as scouting director. The Sox selected outfielder Bryce Brentz and pitcher Anthony Ranaudo in the first round at picks 36 and 39 respectively in his first year. Unfortunately, they passed on pitcher Noah Syndergaard with the first pick, who was drafted in between at pick 38. Infielder Garin Cecchini and pitcher Brandon Workman were also taken in the early rounds. The team made the most of Epstein’s final draft in 2011. Among those selected were outfielders Mookie Betts and Jackie Bradley Jr., catcher Blake Swihart, infielder Travis Shaw, and pitchers Matt Barnes, Noe Ramirez and Henry Owens. Quite a haul. All seven of the aforementioned players have appeared for the 2016 team.

Ben Cherington’s first draft came in 2012 and it was not nearly as successful. Brian Johnson, Deven Marrero, and Pat Light are among the players that have received a cup of coffee in the majors. In 2013, the club had its first top-10 pick in 20 years, drafting at number seven overall. Cherington chose high-school pitcher Trey Ball, who is still very early in his development. The pick raised some eyebrows with outfielder Austin Meadows still on the board, and the two will be forever linked in the minds of many Red Sox draftniks. Other players taken include Teddy Stankiewicz and Mauricio Dubon.

In 2014, the club took shortstop Michael Chavis and fireballing headcase Michael Kopech in the first round, as well as first baseman Sam Travis in the second round.

Mike Rikard replaced Sawdaye after his promotion to VP of Player Development at the conclusion of the disappointing 2014 season. Boston once again owned the seventh overall pick in the 2015 draft. Last year’s selection, outfielder Andrew Benintendi, has been on the fast track to Fenway ever since. The Baseball America College Player of the Year and Golden Spikes Award winner has dazzled in the minors and was recently promoted to AA Portland. The selection of Benintendi was one of Cherington’s final acts as GM before he resigned that August.

The next chapter will be written on June 9 with new GM Mike Hazen making his first selection at number 12 overall. Perhaps this draft class, or other recent draft classes, will turn out to be one of the franchise’s best. Until then, here is a look at some of the draft highlights.

Boston Red Sox Top 10 Draft Picks

Entirely subjective, based on weighing the talent level, impact on the franchise, and where the player was chosen.

Rank Player RD / Year GM
1 Carlton Fisk JAN / 1967 O’Connell
2 Wade Boggs 7 / 1976 O’Connell
3 Roger Clemens 1 / 1983 Sullivan
4 Dwight Evans 5 / 1969 O’Connell
5 Jim Rice 1 / 1971 O’Connell
6 Dustin Pedroia 2 / 2004 Epstein
7 Jon Lester 2 / 2002 Port
8 Nomar Garciaparra 1 / 1994 Duquette
9 Kevin Youkilis 8 / 2001 Duquette
10 Fred Lynn 2 / 1973 O’Connell

Boston Red Sox Best Draft Classes


Round/ Pick # Player Position
1 / 22 Bruce Hurst P
2 / 46 Glenn Hoffman SS
5 / 118 Mike Smithson P
7 / 166 Wade Boggs SS
9 / 214 Gary Allenson C
12 / 286 Reid Nichols 2B
22 / 525 Chico Walker 2B


Round/ Pick # Player Position
1 / 23 Jacoby Ellsbury OF
1 / 26 Craig Hansen P
1 / 42 Clay Buchholz P
1 / 45 Jed Lowrie 2B
1 / 47 Michael Bowden P


Round/ Pick # Player Position
1 / 19 Matt Barnes P
1 / 26 Blake Swihart C
1 / 36 Henry Owens P
1 / 40 Jackie Bradley, Jr. OF
4 / 142 Noe Ramirez P
5 / 172 Mookie Betts OF
9 / 292 Travis Shaw 3B


Scott Maxwell has written about the best free agent signings from each teams in the American League and the National League, the worst free agent signings in Red Sox history, and the worst trade in Red Sox history before the worst trade in Red Sox history.

Follow Scott on Twitter @marbleheader75.

About Scott Maxwell 5 Articles
Scott is a teacher, husband and father living in New Hampshire. His hobbies include travel, collecting baseball cards, playing wiffle ball, and digging in to the history of baseball. He has been a moderator and member of for over a decade and has led discussions with John Henry, Ben Cherington and Mike Hazen.

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