Boston Red Sox top-10 greatest MLB amateur draft picks of all-time
Ranking the best selections that the Boston Red Sox have ever made in the history of the MLB amateur draft, which dates back to 1965.
The MLB draft provides teams with the clearest path to finding cost-controlled young talent. Choose wisely and you may end up with a star player who can be the cornerstone of the franchise for a dirt cheap price, by baseball standards, for the first several years of their major league career. The Boston Red Sox have uncovered many gems in the draft throughout their storied history.
The June amateur draft was instituted in 1965, which means some of the most recognizable names in Red Sox history won’t be found on this list. Ted Williams and Carl Yastrzemski joined the franchise in an era when amateurs could sign with any major league team. They weren’t drafted.
Boston has been home to plenty of star power in recent decades but many of them came here long after they were drafted by other franchises. Pedro Martinez, Curt Schilling, and Chris Sale were acquired in the prime of their careers via trade. Manny Ramirez signed a lucrative deal as a free agent while David Ortiz was scooped up off the scrap heap before revitalizing his career with the Red Sox.
Those icons all left a significant mark on the history of the franchise but they weren’t drafted by this organization. With the 2019 MLB draft on the horizon, we’re focusing on the best selections the Red Sox have made since the process was introduced.
Jon Lester (2002, 2nd round)
The Red Sox have drafted premium talent over the years but their track record developing pitchers leaves a lot to be desired. Spoiler alert, there aren’t many pitchers on this list and none whom the Red Sox have drafted since Jon Lester in 2002 appear to be close to entering the conversation.
Lester made his major league debut in 2006 and was a vital part of a championship team the following season, tossing 5 2/3 shutout innings to earn the win in the decisive Game 4 of the 2007 World Series.
Over parts of nine seasons in Boston, Lester went 110-63 with a 3.64 ERA, 1.28 WHIP, and 8.3 K/9. He made a pair of All-Star appearances and finished as high as fourth on the Cy Young ballot.
The postseason is where Lester shined the brightest and where he developed his reputation as a big game pitcher. He pitched brilliantly during Boston’s run to a World Series championship in 2013, going 4-1 with a 1.55 ERA in five postseason starts.
Boston’s brass misplayed their hand in contract negotiations prior to the 2014 season, leading to a mid-season trade that sent Lester to the Oakland A’s once the Red Sox fell out of contention and it was clear an extension couldn’t be reached. They tried to bring him back in free agency but couldn’t match the steep price the Chicago Cubs were willing to pay.
Lester went on to bring a championship to Chicago and is still going strong in a Cubs uniform but we’ll never forget what he did for us in Boston.
Dustin Pedroia (2004, 2nd round)
Undersized, too slow, not enough power. Those were traits used to describe Dustin Pedroia coming out of Arizona State yet those perceived flaws didn’t persuade the Red Sox to pass over the gritty infielder in the 2004 draft. Pedroia’s work ethic, heart, and dirt-dog attitude would quickly win him over with the fan base and signal that the Red Sox made the right choice.
A rocky start to his career in which he struggled to hit his own weight cast doubt on his future but then-manager Terry Francona stuck with the young second baseman. Patience paid off, as Pedroia captured the Rookie of the Year award in 2007 and won the AL MVP a year later.
The Laser Show owns a .299/.365/.439 lash line throughout his 14 seasons. He’s a four-time All-Star, four-time Gold Glove winner and a Silver Slugger recipient.
A devastating knee injury has wiped out nearly the entirety of the last two seasons for Pedroia and threatens to end his career. It’s been so long since we’ve seen him take the field without the burden of his injury rehabilitation hanging over him that some may have forgotten how great Pedroia was when healthy.
If this truly is the end of the line for Pedroia, it’s certainly not the final chapter he would have written. Yet when it’s all said and done, Pedroia will go down as one of the greatest second basemen in franchise history.
Dwight Evans (1969, 5th round)
Dwight Evans isn’t quite as accomplished as the players he shared a star-studded outfield with but he was an outstanding player in his own right.
Dewey spent the first 19 of his 20 MLB season with the Red Sox, appearing in 2505 games. Only Yastrzemski, his teammate for a dozen seasons, has played in more games with Boston. That longevity is why Evans ranks fourth among Red Sox position players with 64.3 career WAR, per FanGraphs.
Evans hit a solid .272/.369/.473 with 385 home runs during his tenure in Boston. He didn’t put up the staggering numbers that his more heralded teammates did but Evans earned a pair of Silver Sluggers and three All-Star appearances.
His real value came in the field, as Evans collected eight Gold Glove awards to cement his legacy as one of the all-time greatest defensive right fielders.
He also had a knack for coming through when the lights were brightest on the postseason stage. Evans posted a .300 average with three home runs and 14 RBI in 14 World Series games and he was a key member of the ’75 and ’86 teams that fell just short of championship glory.
Fred Lynn (1973, 2nd round)
The New York Yankees actually drafted Fred Lynn out of high school in the 1970 draft but he spurned wearing pinstripes in favor of attending the University of Southern California. Three years later, the Red Sox drafted him in the second round. Boston dodged a bullet when Lynn decided to go to college, ensuring he’d be available for them to take rather than seeing him join their greatest rival.
It’s difficult to fathom a better first full season than the one Lynn had with the Red Sox. The Rookie of the Year award wasn’t enough for the young center fielder, as Lynn added the AL MVP and the first of his four career Gold Glove awards.
As outstanding as his debut season was, Lynn’s best year was 1979 when he won a batting title with a .333 average, blasted 39 homers and drove in 122 RBI. That was somehow good enough for only fourth on the MVP ballot that year.
Lynn would rate higher on this list except that he lasted only six full seasons in Boston before bolting back to his home state of California where he spent the next four seasons with the Angels. He was an All-Star in each of those full seasons wearing a Red Sox uniform yet the lack of longevity in Boston places Lynn only 20th among position players in franchise history with 30.7 fWAR.
Carlton Fisk (1967, 1st round)
From 1966-1986, MLB held an amateur draft in January prior to the June draft that we’re familiar with today. Carlton Fisk was one of three players selected by the Red Sox in the 1967 January amateur draft.
The Hall of Fame catcher made brief appearances in 1969 and 1971 with the big league club before breaking out with a Rookie of the Year campaign in 1972. Fisk made the All-Star team, won a Gold Glove and finished fourth on the AL MVP ballot in his first full major league season.
Perhaps the most memorable moment of Fisks’ career was his walk-off home run in Game 6 of the 1975 World Series. The lasting impression of that game was Fisk trying to wave the ball fair as it hooked toward the left field foul pole.
Fisk spent 11 seasons with the Red Sox, hitting .284/.356/.481 in 1078 games. He was a seven-time All-Star and won a Silver Slugger during his time in Boston.
He went on to play 13 more seasons with the Chicago White Sox to cap a lengthy career that extraordinarily lasted until he was 45 years old. While he spent the majority of his time wearing different color Sox, most of his prime years came with the Red Sox. The organization clearly agreed when they retired his No. 27 at Fenway Park.
Nomar Garciaparra (1994, 1st round)
Nomar Garciaparra emerged during a Golden Age for shortstops, joining Derek Jeter and Alex Rodriguez to form a holy trinity at the position. There was a time when Red Sox fans would vehemently argue that Nomaaah was the best of the trio and the notion wasn’t entirely crazy.
Garciaparra was named Rookie of the Year in 1997 when he hit .304 with 30 home runs and 22 steals while leading the league with 209 hits and 11 triples. He took another leap in his Sophmore campaign, setting career-highs with 35 home runs and 122 RBI to finish as the runner-up for the MVP.
Nomar won a pair of batting titles in 1999 and 2000, sporting a .372 average in the latter season. There were many at the time who compared the sweet swing of Garciaparra to the great Ted Williams and thought he had the best chance of any modern player to hit .400 for a season. He never made it to that level but only six major league players have topped Garciaparra’s career-high .372 average in the years since Teddy Ballgame hit .406 in 1941 (including Williams himself, who hit .388 in 1957).
Garciaparra made five All-Star appearances in his first six full seasons, excluding 2001 when a wrist injury limited him to 21 games. He would return from that lost year to produce two more All-Star worthy seasons but Garciaparra was never quite the same after hurting his wrist and never returned to the astonishing level he showed early in his career.
Unfortunately, injuries continued to pile up for Nomar, spoiling the second half of his career. His relationship with the Red Sox soured during an injury-plagued 2004 season, turning him into a bit of a malcontent and stamping his ticket out of town. He was traded to the Chicago Cubs in a three-team deal that brought Orlando Cabrera in as his replacement at shortstop, depriving Garciaparra of being part of the curse-breaking World Series championship run that year.
His tenure in Boston may not have ended well but it started out as promising as any position player in recent memory. Fading under the weight of multiple injuries in the second act of his career kept him out of Cooperstown but there’s no doubt that Nomar was well on his way toward being an all-time great hitter during his years in Boston. Garciaparra was recognized for those efforts in 2014 when he was inducted into the Red Sox Hall of Fame.
Jim Rice (1971, 1st round)
Remember when we talked about how great Fred Lynn was as a rookie? Jim Rice was almost as great, finishing as the runner-up to his teammate in the Rookie of the Year race and third on the MVP ballot.
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Lynn may have gotten off to a slightly better start but Rice had the better overall career, especially if we’re focusing on the years in Boston. Rice spent all 16 seasons of his Hall of Fame career with the Red Sox.
Rice bashed 25+ homers seven times in his career, leading the league on three occasions. His career-high of 46 home runs came in his MVP campaign of 1978 when he also led the league with 139 RBI, 213 hits, 15 triples, a .600 SLG and .970 OPS.
The eight-time All-Star finished in the top-five on the MVP ballot six times but only took home the hardware once.
Rice is fourth in franchise history with 2089 games played. His many years of strong production in Boston is why he ranks seventh among position players in franchise history with 50.8 fWAR.
Rice’s No. 14 will forever hang at Fenway as one of 10 numbers retired by the franchise.
Mookie Betts (2011, 5th round)
It’s hard the believe that this five-tool stud fell to the fifth round but the Red Sox are still reaping the benefits of drafting Mookie Betts.
Betts produced a solid rookie season, hitting .291 with a .820 OPS, 18 home runs, and 21 steals. The following season was his true breakout year though, as he made his first of three consecutive All-Star appearances (with a fourth almost certainly on the way this summer). In 2016, Betts hit .318/.363/.534 with 31 home runs, 113 RBI and 26 steals to finish as the runner-up in the MVP race.
Two years later, Betts would take home the MVP hardware, along with a batting title, and Silver Slugger award. He hit .346 with a 1.078 OPS, 32 home runs, and 20 stolen bases.
As great as Betts has been at the plate, he’s even better in the field. With three Gold Glove Awards in his four full MLB seasons and a staggering 96 defensive runs saved in 501 career games at the position, Betts is on his way to becoming the best defensive right fielder in franchise history.
It may seem premature to rank Betts this high, ahead of Hall of Famers and those who proved themselves over a far longer period of time. That’s fair, although we can’t ignore that Betts is on pace to have a better career than any of them and he’s only 26 years old.
Mookie is already 18th among Red Sox position players with 32.3 career fWAR, while everyone ahead of him on that list has at least one more season of experience in Boston under their belts. There’s plenty of time for him to pile up more awards while adding to his statistical resume.
Wade Boggs (1976, 7th round)
If drafting Betts in the 5th round was a great value, Wade Boggs in the 7th round is an absolute steal.
Boggs spent the first 11 seasons of his career in Boston, finishing third in the 1982 Rookie of the Year race and making eight of his 12 career All-Star appearances during his tenure here.
Despite his numerous accolades that paved his way to Cooperstown, Boogs always seemed a bit underrated because he lacked the flashy home run totals in an era when power threats were surging across baseball. It’s not that Boggs couldn’t hit home runs, as he proved by blasting 24 in 1987. He simply wasn’t trying to swing for the fences at the expense of his primary goal – getting on base.
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His philosophy paid off as few were as adept as Boggs when it came to avoiding outs. He won five batting titles and led the league in on-base percentage six times. Boggs owned a slash line of .338/.428/.462 during his years in Boston and won six Silver Sluggers.
While some fans haven’t forgiven Boggs for leaving to join the rival Yankees, he spent most of his career – certainly the best years of his career – with the Red Sox. His 70.8 fWAR compiled during those 11 years in Boston places him third among position players in franchise history.
Boggs is one of only 10 players to have their number retired by the organization. His No. 26 hangs on the right field facade at Fenway Park alongside only two other players (Fisk, Rice) who were drafted by the Red Sox.
When factoring in where he was selected, it’s tough to top the value that the Red Sox received by drafting Boggs.
Roger Clemens (1983, 1st round)
Remember when I mentioned that the Red Sox don’t have a great track record of drafting pitchers? That remains true, with one of the rare exceptions being perhaps the greatest pitcher of the modern era.
The name Roger Clemens has been dragged through the mud, stained by his association with the steroid era. Before all that, long before there was any evidence of his alleged cheating, Clemens was a dominant force for 13 seasons with the Red Sox.
The Rocket earned a record seven Cy Young Awards in his career, three of which came in a Red Sox uniform. His first Cy Young came in 1986, coinciding with the rare honor of a pitcher winning the MVP. Clemens captured the pitcher’s Triple Crown that year, leading the league with 24 wins, a 2.48 ERA, and 0.96 WHIP.
Clemens led the league in strikeouts three times during his years in Boston, including 291 strikeouts in 1988, which stands as the third-most in a single season by a Red Sox pitcher. Four of the top 10 strikeout seasons in franchise history belong to Clemens.
Only four major league pitchers have ever recorded a 20-strikeout game and Clemens is the only one to do it twice. He punched out 20 Seattle Mariners in 1986 and tied his own single-game record by striking out 20 Detroit Tigers a decade later.
Clemens was a workhorse, routinely topping 200 innings during a seven-year stretch in Boston. That included a league-leading 271 1/3 innings in 1991, a workload that seems unfathomable in today’s bullpen oriented era. He led the league in shutouts five times and compiled 38 of them with the Red Sox. Starting pitchers rarely go the distance these days yet Clemens made it seem like an expectation when he took the mound.
The Red Sox let Clemens walk away in free agency when they felt he was in the twilight of his career. He would end up proving them wrong by capturing four more Cy Youngs.
Regardless of how his reputation was tainted by the tail end of his career, none of that matters when evaluating his time in Boston. Clemens is the most accomplished starting pitcher in Red Sox history. He’s tied for the franchise record with 192 career wins and leads all pitchers in franchise history with 76.8 fWAR.
Any hard feelings between the organization and their former pitcher were buried in 2014 with Clemens was elected into the Red Sox Hall of Fame.
Next. Ranking Red Sox retired numbers. dark
Clemens is at least in the conversation for the best player at any position to wear a Red Sox uniform and he’s undoubtedly the best player they have ever drafted.