MLB Draft: Best players taken by Red Sox in each round
1st Round — Roger Clemens, 1983
19th overall (University of Texas)
Honorable mention: Jim Rice (1971), Nomar Garciaparra (1994), Bruce Hurst (1976), Mo Vaughn (1989), Andrew Benintendi (2015), Jacoby Ellsbury (2005)
This one is between Clemens and Rice, but is that even a discussion? Jim Ed was one of the most feared sluggers of the '70s and '80s and ultimately earned his place in Cooperstown, but Clemens might be a top-five pitcher ever. He spent 24 years in the big leagues, won over 350 games, and took home seven Cy Young Awards. He also revitalized the franchise after the barren early 1980s, and then he made a seamless heel turn in the late '90s with the Yankees. Who can forget: "Where is Roger? In the shower!" He'd have joined Rice in the Hall of Fame a long time ago, but the taint of steroids might disqualify him forever.
2nd Round — Fred Lynn, 1973
41st overall (USC)
Honorable mention: Dustin Pedroia (2004), Jon Lester (2002)
In their own way, each man on this list represents a great what-might-have-been. Both Lynn and Pedroia won Rookie of the Year and MVP awards — Lynn did it in the same magical 1975 season — but what separates him from the Laser Show is his incredible natural ability. A generation of Red Sox fans still considers Lynn's swing the sweetest they've ever seen. The trade that sent him to California for Frank Tanana in 1981 remains heartbreaking. Injuries kept Pedroia from completing what could've been a Hall of Fame career, and we'll always wonder what would've happened if the Red Sox had just kept Lester in 2014.
3rd Round — Mike Greenwell, 1982
72nd overall (North Fort Myers HS)
Honorable mention: Scott Cooper (1986)
Some pretty great players have been selected in the third round, like Hall of Famers Dennis Eckersley, Bert Blyleven, and Tony Gwynn. The Red Sox, by contrast, have consistently whiffed. The one pick they nailed was Greenwell, a two-time All-Star who finished second to a chemically enhanced Jose Canseco in the 1988 MVP race. Greenwell spent 12 years in Boston and was remarkably underrated, retiring in 1996 with a lifetime average of .303 and an .831 OPS. As for Cooper, he might be the worst two-time All-Star in history, but he spent seven years in the big leagues.
4th Round — Jeff Bagwell, 1989
110th overall (University of Hartford)
Honorable mention: Jonathan Papelbon (2003), Ty Buttrey (2012)
The Red Sox had a 1990 division title to win when they beat the August trade deadline by acquiring veteran reliever Larry Andersen from the Astros. And man did Anderson deliver, striking out 25 and posting a 1.23 ERA in 22 innings while pitching every other day down the stretch. The Double-A prospect who headed west had an intriguing bat, but lacked power. Nearly 30 years later, the Bagwell trade remains a cautionary tale for GMs looking to upgrade flawed rosters. For one month of Andersen, the Red Sox sacrificed a Hall of Famer. They at least held on to Papelbon, who ended up closing a World Series.
5th Round — Mookie Betts, 2011
172nd overall (Overton HS, Nashville, Tenn.)
Honorable mention: Dwight Evans (1969), John Valentin (1988), Amos Otis (1965)
Now we're talking. The Red Sox have found some serious talent in the fifth round, and while a case can be made for the criminally underrated Evans — his lifetime WAR of 67.1 dwarfs Rice's 47.7, and yet he never received more than 10.4 percent of the Hall of Fame vote — we're giving the nod to Betts, who has already won one MVP award and finished second in another vote just six years into his career. They're the two stars of a round that includes Valentin, a former All-Star, as well as Otis, a Gold Glover who went on to greater fame with the Royals.
6th Round — Anthony Rizzo, 2007
204th overall (Stoneman-Douglas HS, Parkland, Fla.)
Honorable mention: Cecil Cooper (1968), Paul Quantrill (1989), Don Aase (1972)
When the Red Sox acquired Adrian Gonzalez from the Padres in 2010, it was inconceivable that Gonzalez wouldn't be the best player in the trade. And yet nearly a decade later, there's no question that if Theo Epstein could do it again, he'd simply keep Rizzo, whom he went on to reacquire with the Cubs. Rizzo survived cancer as a member of the Red Sox and has thrived with the Cubs, making three All-Star teams and winning a Gold Glove and a World Series. Cooper experienced a similar career arc, rising to prominence only after he left Boston and became a slugging All-Star with the Brewers.
7th Round — Wade Boggs, 1976
166th overall (Plant HS, Tampa, Fla.)
Honorable mention: None
Nothing came easily for Boggs in his early years. Considered a borderline hitting prospect, he nonetheless caught the eye of Red Sox scout George Digby, who convinced him to sign for $7,500. After six years in the minors — where he hit .318 — the Red Sox finally summoned him in 1982, just a couple of months shy of his 24th birthday. He hit .361 a year later to win the first of five batting titles and was off, his left-handed swing tailor-made to curl balls off the Monster. He remains the only player of note the Red Sox have drafted in the seventh, though last year's pick, second baseman Jarren Duran, is currently hitting .400 at High-A Salem after debuting with a Boggsian .357 in 2018.
8th Round — Kevin Youkilis, 2001
243rd overall (University of Cincinnati)
Honorable mention: Tim Naehring (1988), Jody Reed (1984), Al Nipper (1980)
Youkilis likes to tell the story of hitting .400 as an underclassman at Cincinnati and going undrafted, but Virginia Tech quarterback Michael Vick, who hadn't played baseball since high school, managed to get selected in 2000. As a college senior with no leverage, Youkilis signed for peanuts and then made every team that passed on him regret it by making three All-Star teams, winning a Gold Glove, and playing a pivotal role in the 2007 World Series championship. The Red Sox also scored with the versatile Naehring and Reed, a doubles machine at second base in the early 1990s.
9th Round — Travis Shaw, 2011
292nd overall (Kent State)
Honorable mention: Christian Vazquez (2008)
Like some other players on this list, Shaw has risen to prominence elsewhere, compiling back-to-back 30-homer seasons with the Brewers in 2017 and 2018. He was never considered a frontline prospect with the Red Sox, overshadowed by toolsier players like Yoan Moncada, Rafael Devers, and Andrew Benintendi. But the son of former All-Star closer Jeff Shaw kept plugging along, hitting 16 homers with the 2016 Red Sox before being shipped to the Brewers in a regrettable trade for oft-injured reliever Tyler Thornburg. One miss at this spot: the Red Sox took Mark Teixeira in 1998, but he had a nasty negotiating experience and didn't sign.
10th Round — Brady Anderson, 1985
257th overall (Cal-Irvine)
Honorable mention: Shea Hillenbrand (1996), Lou Merloni (1993)
If you're sensing a pattern, it's that the Red Sox tend to give up on their best low-round picks before they reach the majors. In the case of Anderson, he went to the Orioles for Mike Boddicker in the 1988 trade that included future All-Star Curt Schilling. It took Anderson nearly a decade to break out — his 50-home run 1996 season signified that perhaps the explosion in power across the game wasn't exactly on the up-and-up — but Anderson became a mainstay in Baltimore, where he made three All-Star teams. That's only one more than Hillenbrand. As for Merloni, Framingham Lou hit .271 over nine seasons.
11th Round — Ben Oglivie, 1968
248th overall (Roosevelt HS, Bronx, NY)
Honorable mention: Freddy Sanchez (2000), Ryan Pressly (2007)
Oglivie took a circuitous path to stardom. He hit just .235 in parts of three seasons with Boston before being traded first to the Tigers and then the Brewers, where he became a three-time All-Star and key cog in Harvey's Wallbangers alongside fellow former Red Sox draftee Cecil Cooper. He retired with 235 homers, including a league-leading 41 in 1980. Steady Freddy won a batting title and made three All-Star teams with the Pirates, while Pressly has emerged as one of the best setup men in baseball after being taken by the Twins in the 2012 Rule 5 draft.
12th Round — Lew Ford, 1999
379th overall (Dallas Baptist University)
Honorable Mention: Jalen Beeks (2014), Reid Nichols (1976)
Ford arrived at the tale end of the Dan Duquette years, when Red Sox prospects were scarce. And while he was consistently overshadowed by Michael Coleman, who dubbed himself "Prime Time" before hitting .194 in parts of three seasons, Ford ended up carving out a six-year career, including an out-of-nowhere 2004 with Minnesota that saw him hit .299 with 15 homers, 72 RBIs and 20 steals, good for two MVP votes. We'll see what Beeks becomes, but for now he's a useful member of Tampa's deep bullpen.
13th Round — Carl Pavano, 1994
355th overall (Southington (Conn.) HS)
Honorable mention: Tim Blackwell (1970)
The pride of Southington had a nice Red Sox career ahead of him, but then GM Dan Duquette saw an opportunity to acquire Pedro Martinez from the Expos. Pavano headed north of the border with fellow right-hander Tony Armas Jr. and ended up spending 14 years in the big leagues. His best season came in 2004 with the Marlins, when he went 18-8 with a 3.00 ERA and finished sixth in the Cy Young voting. Though injuries kept him from realizing his full potential, he still won over 100 games, and he's one of only three pitchers to throw at least seven complete games in a season since 2009.
14th Round — Bobby Poyner, 2015
411th overall (University of Florida)
Honorable Mention: None
The Red Sox have only drafted four players in the 14th round to reach the majors and two of them -- Pedro Alvarez and Matt LaPorta -- didn't sign, so the pickings are slim. Poyner gets the nod over fellow left-hander R.J. Swindle, with 22 appearances and a 3.86 ERA over the last two seasons.
15th Round — Ernie Whitt, 1972
352nd overall (Macomb CC, Warren, MI)
Honorable mention: Cory Bailey (1991)
Whitt was one of the better catchers of the 1980s in Toronto, but he had no chance of ever playing in Boston, thanks to the presence of Hall of Famer Carlton Fisk. The rugged backstop actually debuted with the Red Sox in 1976, appearing in eight games and launching his first homer, but the Blue Jays selected him in the expansion draft that fall and he went on to make an All-Star team and become a solid 15-homer-a-year catcher in an era when that qualified as impressive power.
16th Round — Oil Can Boyd, 1980
413th overall (Jackson State)
Honorable mention: None
His given first name was Dennis, but fans of that era will never forget the Can, who belongs alongside Luis Tiant and Dennis Eckersley as one of the most boisterously demonstrative pitchers in Red Sox history. He won 60 games during eight tumultuous seasons in Boston and authored a career-year in 1986, when he won 16 games, including the AL East clincher with a complete game over the Blue Jays. He started Game 3 of the 1986 World Series and remains a fan favorite.
17th Round — Josh Reddick, 2006
523rd overall (Middle Georgia College)
Honorable mention: Tim Van Egmond (1991)
Once you reach this point in the draft, prospects must overcome the stigma of why they were taken so low in the first place. Case in point: Reddick. He played on some stacked minor league squads, including a 2007 Portland team that included Jacoby Ellsbury, Clay Buchholz, and Jed Lowrie. He often took a back seat to more hyped players like Lars Anderson and Ryan Kalish, but Reddick has gotten the last laugh. He hit 32 homers and won a Gold Glove with the A's in 2012, he hit .314 and won a World Series with the Astros in 2017, and he remains a useful member of the Astros today.
18th Round — Ron Mahay, 1991
486th overall (South Suburban College (Ill.))
Honorable mention: Hunter Strickland (2007)
The pickings get understandably slimmer once you start approaching the 500th selection in any given draft, but the Red Sox did find a 14-year big-leaguer in Mahay, who was drafted and debuted as an outfielder in 1995 — homering off of California's Mike Butcher — before returning to the minors and converting to relief. He returned in 1997 to go 3-0 with a 2.52 ERA and retired 13 years later with a 3.83 ERA in 514 games.
19th Round — David Eckstein, 1997
581st overall (University of Florida)
Honorable mention: None
No one who looked at the 5-foot-6 Eckstein pegged him as a big leaguer, especially considering his unorthodox swing and throwing motion. The Red Sox saw him hit .313 at Double-A Trenton in 1999 and decided to tinker anyway. They shortened his stroke with disastrous results — he hit just .246 at Triple-A Pawtucket in 2000 before being dropped from the 40-man roster and claimed that August by the Angels. He finished fourth in the Rookie of the Year voting a year later with his old wraparound swing and ended up making two All-Star teams while winning World Series as a starting shortstop in Anaheim and St. Louis.
20th Round — Tom Bolton, 1980
517th overall (Antioch (Tenn.) HS)
Honorable Mention: Alex Meyer (2008)
The Red Sox took a couple of fliers on future All-Stars Jack McDowell in 1984 and Charlie Blackmon (as a left-handed pitcher) in 2005, but neither signed for obvious reasons. McDowell went fifth overall three years later, while Blackmon ended up being a second-round pick of the Rockies. Bolton's claim to fame is going 10-5 with a 3.38 ERA in 1990 and helping the Red Sox to a division title.