Boston Red Sox: 10 biggest first-round draft pick disasters

The worst first-round draft picks in Red Sox history.

The MLB draft is more hit-or-miss than the selection process in any other sport. Much of this has to do with baseball players taking years to develop before they are ready to crack the majors. The top draft picks in the NBA and NFL can pay immediate dividends but no baseball player is ready to step in and contribute in the big leagues right away. The lengthy grooming process increases the chances of those prospects becoming a bust and the Boston Red Sox have had their fair share of wasted picks over the years.

The MLB amateur draft dates back to 1965, so we’re focused on players selected by the Red Sox under this system since then. The goal is to pinpoint years when the Red Sox made a first-round pick who didn’t pan out when a future star was still on the board at the time.

Keep in mind that there were several years when the Red Sox didn’t possess a first-round pick. They also picked near the end of the round in many years so even if they whiffed on their pick, there weren’t many selections behind them in that opening round.

While digging deeper could lead to even more fascinating finds, we’re only counting players selected in the first round. Some players are simply late bloomers. J.D. Martinez was a 36th-round pick who developed into a superstar after reinventing his swing. We can’t blame the Red Sox for not using a first-round pick on a player if every other team passed on them at least once.

We can criticize them for passing on a player identified by another organization as a worthy first-round selection in favor of one who proved to be a bust. In chronological order, here are 10 draft classes where that happened.

Red Sox 1967 Draft

No. 3 – Mike Garman, No. 23 – Danny Graham
No. 27 – Vida Blue (A’s)

The Red Sox had a pair of first-round picks in 1967, including the third overall pick. Mike Garman had a sold nine-year career after finding success as a reliever after he left Boston but his tenure with the Red Sox was uninspiring. He owned a 4.95 ERA in 20 appearances (six starts) spread over parts of four seasons. Garman eventually found his niche but more was expected from a former No. 3 overall pick.

Boston’s second selection in that first round was used on Danny Graham, who never made it further than Double-A in his three-year minor league career.

One of those picks could have been used on Vida Blue, who lasted almost until the end of the round. Blue’s first full season in the majors came in 1971 when he earned the AL Cy Young and MVP awards for the Oakland A’s by going 24-8 with a 1.82 ERA.

That career year came early for Blue but he would end up making six All-Star appearances and finishing in the top-seven on the Cy Young ballot four more times. Blue was also a key contributor to three World Series titles with Oakland in the 1970s.

Red Sox 1974 Draft

No. 20 – Edward Ford
No. 21 – Rick Sutcliffe (Dodgers)

Edward Ford never made it to the majors so it’s safe to classify him as a bust. One pick later, the Los Angeles Dodgers took Rick Sutcliffe.

The right-hander put himself on the radar with a Rookie of the Year campaign in 1979, winning 17 games with a 3.46 ERA.

The Dodgers traded Sutcliffe to Cleveland after parts of five seasons and he immediately broke out by winning an ERA title with the Indians in 1982. He made his first of three career All-Star appearances the following year.

A rocky beginning to the 1984 season led to Cleveland shipping Sutcliffe to the Chicago Cubs. He responded by going 16-1 with a 2.69 ERA down the stretch to earn the NL Cy Young and lead his new team to a division title.

Sutcliffe didn’t have the most consistent career but he had some excellent seasons at his peak and could have helped put some great Red Sox teams of the 1980s over the top. That’s assuming that Boston didn’t give up on him early in his career, as two other franchises did.

Red Sox 1985 Draft

No. 21 – Dan Gabriele
No. 22 – Rafael Palmeiro (Cubs)

If you’re seeing a trend of Red Sox draft picks who never made it to the majors, you’re not wrong. That’s going to be the case for a lot of the players on this list. Right-handed pitcher Dan Gabriele is no different, having never made it beyond Double-A.

Rafael Palmeiro wasn’t much of a power threat in his early years before his steroid-enhanced peak but he did make an All-Star team with the Cubs in 1988. He was traded to the Texas Rangers after that season amid rumors of an affair with the wife of teammate Ryne Sandberg.

The four-time All-Star bashed 38+ home runs in nine consecutive seasons and finished his career with 569, the 13th-most in MLB history.

Jose Canseco identified Palmeiro as a steroid user, claiming he injected his teammate himself. In 2005, Palmeiro testified under oath at a Congressional hearing that he “never” used steroids and any rumors to the contrary were false. Canseco isn’t exactly the most reliable source but when Palmeiro tested positive for a PED in August of that year, he lost all credibility.

Palmeiro has a controversial past that Red Sox fans may prefer to have never been a part of but there’s no denying that he was a far better value than Gabriele late in the first round of the 1985 draft.

Red Sox 1995 Draft

No. 15 – Andrew Yount
No. 17 – Roy Halladay (Blue Jays)

Andy Yount had a promising debut in Rookie ball after the Red Sox selected him with the No. 15 overall pick in 1995 but his career quickly fizzled out after a miserable campaign the following year in Low-A Lowell. He latched on with the Detroit Tigers organization a few years later but converted to an outfielder after a pair of underwhelming seasons on the mound in A-ball. Yount couldn’t cut it with the bat either and his minor league career ended before he could advance beyond High-A.

If the Red Sox were intent on selecting a right-handed high school pitcher, they should have went with Roy Halladay. Instead, they left the future Hall of Fame pitcher for the division rival Toronto Blue Jays to take two picks later.

Halladay had some early career struggles, infamously being sent all the way back to Single-A to rebuild his delivery following a brutal 2000 season in the majors. By 2002, Halladay was one of the best pitchers in the game.

The eight-time All-Star won a pair of Cy Young awards in his 16-year career. He finished as the runner-up twice and had three others seasons where he finished in the top five.

Halladay spent 12 seasons with the organization that drafted him before the Blue Jays traded him to Philadelphia. He won his second Cy Young in his first season with the Phillies, highlighted by a perfect game in May of that season. Halladay helped the Phillies reach the NLCS that year by throwing a no-hitter in his first career postseason start.

The Red Sox were one of the rare teams that had some success against Halladay but they still would have been better off if he were pitching for them instead of against them.

Red Sox 1998 Draft

No. 12 – Adam Everett
No. 20 – CC Sabathia (Indians)

Finally, we get back to a player selected by the Red Sox in the first round who didn’t wash out in the minor leagues. Adam Everett had a solid 11-year career in the majors as a defensive-minded shortstop. Unfortunately, none of those seasons were in Boston. He was traded as a prospect to the Houston Astros for Carl Everett, a more productive player whose talent was offset by his bizarre behavior.

Everett was more successful than any other “bust” on this list but he never quite lived up to his lofty draft status.

The same can’t be said for CC Sabathia. The lefty was a six-time All-Star who won the Cy Young award in his final full season with the Indians in 2007.

Cleveland traded Sabathia to Milwaukee mid-way through the 2008 season and he finished the year by going 11-2 with a 1.65 ERA to fuel the Brewers to a surprising playoff appearance.

The Yankees lured Sabathia to the Bronx with a lucrative free-agent deal in 2009. The southpaw helped pitch the Yankees to a World Series title that year with Sabathia earning MVP honors in the ALCS.

His 251 career wins ties Sabathia with Bob Gibson for 47th in MLB history, giving him a decent shot of making the Hall of Fame when he becomes eligible.

Cleveland wasn’t willing to pay to keep their ace as free agency approached but assuming the Red Sox would have, they might have kept him away from the Yankees and potentially prevented them from winning their last championship.

Even if Boston let him walk after the 2008 season, Sabathia could have put them over the top in 2003 and his presence would have dulled the pain of losing Pedro Martinez after the 2004 season.

Red Sox 2000 Draft

No. 22 – Phil Dumatrait
No. 29 – Adam Wainwright (Braves)

Here we have another failed Red Sox draft pick who at least made it to the majors. Like Everett before him, Phil Dumatrait was no longer with the Red Sox by the time he made his big league debut in 2007. Unlike Everett, Dumatrait didn’t find modest success at this level. He was 4-13 with a 6.20 ERA in 87 career appearances with three different teams and he hasn’t appeared in the majors since 2011.

Shortly after the Red Sox wasted a pick on Dumatrait, the Atlanta Braves selected Adam Wainwright. The Braves made a mistake of their own by trading Wainwright to the St. Louis Cardinals for J.D. Drew in 2003. Despite that Boston handed Drew a lucrative free-agent contract a few years later, let’s pretend that they wouldn’t have been foolish enough to make that trade.

Wainwright has had a successful 14-year career with the Cardinals. He made three All-Star appearances and finished top-three on the NL Cy Young ballot on four occasions.

He can do more than just pitch. Wainwright has a pair of Gold Glove awards and a Silver Slugger on his mantle.

The 37-year-old is under contract with the Cardinals for 2020 and it’s unclear if his career will continue beyond that but he’s certainly done plenty to earn his first-round draft status.

Red Sox 2010 Draft

No. 20 – Kolbrin Vitek
No. 23 – Christian Yelich (Marlins)

Kolbrin Vitek spent parts of four seasons bouncing around to various levels of Single-A with a couple of brief stints with Double-A Portland. He was primarily a third baseman but moved to left field in 2013 before his career came to an end.

While the player who the Red Sox picked saw his career crumble years ago, Christian Yelich has since emerged as one of the best in the game. The 2018 NL MVP was the runner-up for the award last season.

Yelich’s superstar breakout didn’t come until after the Marlins traded him to the Brewers. However, he was still a young five-tool talent who was steadily improving during his tenure in Miami. His emergence didn’t come out of nowhere. Miami traded him as part of their plan to blow up the roster and reduce their payroll to one of the league’s lowest.

The Red Sox clearly wouldn’t have given away a blossoming star simply because he was getting expensive and might leave them in free agency in the near future. Oh wait, that’s exactly what they did with Mookie Betts. So, make that two MVP-caliber outfielders who would currently be anchoring the Red Sox outfield if they hadn’t failed in the draft and in payroll management.

Red Sox 2013 Draft

No. 7 – Trey Ball
No. 9 – Austin Meadows (Pirates)

The Red Sox have rarely selected as high as No. 7 overall in the draft. The last time they picked in that spot it turned out pretty well with Andrew Benintendi. Two years earlier, they completely whiffed with Trey Ball.

Ball owned a 33-46 record and an ERA north of 5.00 in six minor league seasons. The Red Sox converted him to a reliever in Double-A but he was even worse in that role. He became a two-way player by spending some time in the outfield but he couldn’t hit either. Ball appeared in only five games as an outfielder last year and didn’t pitch at all. He was let go when his contract expired after the season. When taking into account how high he was selected, Ball is arguably the biggest bust on this list.

Boston probably didn’t pass on any future Hall of Fame players in the first round that year but several who were selected after Ball had breakout years in 2019. Austin Meadows leads the way as the only one of that group who made an All-Star appearance. He was having a solid rookie season the previous year before the Tampa Bay Rays stole him from Pittsburgh in the ill-fated Chris Archer deal.

By selecting Ball early in the first round, Boston passed on Hunter Dozier (selected No. 8 by the Royals). He belted 26 homers and led the league with 10 triples last year. Tim Anderson (No. 18 overall) won a batting title for the White Sox last season.

I made the point of sticking only to players selected in the first round but I’d be remiss not to mention that 2019 NL MVP Cody Bellinger was selected by the Dodgers in the fourth round that year. Every other team passed on Bellinger multiple times so we can’t be too hard on the Red Sox for not pulling the trigger on him with the 7th overall pick.

Still, looking back at the previous slide, it’s hard not to notice that the Red Sox potentially could have had the NL MVP from each of the last two years in their lineup right now if they drafted wisely.

Red Sox 2016 Draft

No. 12 – Jay Groome
No. 20 – Gavin Lux (Dodgers)

We’ll wrap up with a player who hasn’t necessarily failed yet and one who has yet to prove himself at the major league level.

Jay Groome was a very talented pitcher who evaluators were extremely high on when the Red Sox drafted him 12th overall a few years ago. He flashed that potential in Rookie ball and Low-A during his brief pro debut in 2016 but the wheels feel off the following year. Groome ended up needing Tommy John surgery and missed the entire 2018 season.

Groome has only tossed a total of four innings since returning to the mound last year. He has a long road ahead to build himself back up and try to rediscover the form that once made him a first-round pick. He might pan out eventually but Groome’s stock has clearly plummeted.

While every other draft class on this list has focused on a future All-Star that the Red Sox missed out on in the first round, Gavin Lux has a mere 23 games under his belt at the major league level. He has much more to prove before we can truly regret passing on him.

However, MLB Pipeline ranks Lux as the second-best prospect in baseball for a reason. A thin Red Sox farm system only has one prospect ranked in the top 50. Having a young player of Lux’s caliber would have completely changed the outlook of the future of this organization.

Perhaps it’s too soon to include the first round of the 2016 draft on this list but it’s certainly trending in that direction with Lux ready to contribute to a championship contender while Groome is still trying to find his form in the lower levels of the minor league system.