Looking back at the most hyped prospects in recent Red Sox memory

Red Sox SS Hanley Ramirez

Many young Red Sox fans may forget that before Hanley Ramirez was a slugging first baseman who came over via free agency in 2015, he was a highly regarded five-tool prospect in the Sox system. Ramirez signed with Boston as a 16-year-old in 2000, and began to make waves in the 2002 season. The shortstop hit .371 in 22 games in Single-A Lowell, a remarkable achievement for an 18-year-old.

By 2005, it was clear Ramirez was ready for the big leagues. He entered the season as the number 10 prospect in all of baseball, and, despite being three years younger than the average player in Double-A, hit .271 and stole 26 bases in Portland. He was so impressive that the Red Sox added him to the major league roster in September despite never playing a game at Triple-A.

Alas, this is where the story takes an unexpected turn. Because the Red Sox were in the thick of the pennant race, Ramirez got just two plate appearances in the majors, both ending in strikeouts. Those would be the last at-bats he got in Boston for a decade, as he became the centerpiece of a deal that brought Josh Beckett and Mike Lowell to town and sent Ramirez down to Florida to become the new face of the franchise.

The deal would become a bittersweet one for the Red Sox and their fans. Yes, Lowell and Beckett did play crucial roles in the 2007 Championship run, Ramirez would become an MVP candidate down in Florida while the Red Sox would cycle through mediocre shortstops for the next half-decade.

The idea of prime Hanley Ramirez batting in front of Dustin Pedroia, Kevin Youkilis, and David Ortiz is a tantalizing one, but it will, unfortunately, remain just a hypothetical.

Red Sox SP Clay Buchholz

Who was the last Red Sox pitching prospect to receive as much hype as Brayan Bello? You might be surprised at how long it has been. Sure, Jon Lester, Jonathan Papelbon, and Henry Owens were well-regarded in the minor leagues, but none of those three can match the excitement surrounding Clay Buchholz.

Buchholz was selected with the 42nd pick of the 2005 MLB draft, which was actually a compensation pick the Red Sox received for losing Pedro Martinez. From the very beginning, he proved he was well worth it.

He finished off the 2005 season by posting a 2.61 ERA in 15 starts in short-season Lowell, then spent 2006 overmatching opposing A ball hitters to earn a late season promotion to High-A Wilmington, where he allowed just two runs in 16 innings.

Buchholz continued to make steady progress in the 2007 season, earning a spot in the Futures Game along the way. He pitched well in a one-start callup in August (six innings, three earned runs), but it was his second start, a no-hitter against the Orioles, where the hype surrounding the youngster reached a fever pitch.

Though he was shut down with shoulder fatigue before the postseason began, Buchholz entered the 2008 season as the number six prospect in baseball and with a spot in the starting rotation.

Despite Buchholz lasting 10 years with the Red Sox, he didn’t quite live up to the hype.  Injuries would define his Boston career, as he never made 30 starts in a season and only topped 22 three times, and he was often ineffective when he was healthy.

There were glimpses of greatness, like his 2010 season where he had a 2.33 ERA and finished sixth in Cy Young voting, but he was never the frontline starter that he appeared during that magical night in 2007.

Red Sox CF Jacoby Ellsbury

Few players have a more complicated Red Sox legacy than Jacoby Ellsbury. On one hand, he was a two-time World Series champion, an All-Star, an MVP candidate, and a three-time stolen base champion. On the other hand, he was frequently injured, only hit more than ten home runs once, and, worst of all, signed a seven-year contract with the hated Yankees.

Before any of this, however, Ellsbury was a five-sport athlete at Madras High School in Oregon. Though he put up eye-popping football and basketball numbers, baseball was his best sport, as he hit .537 with 65 stolen bases in his senior year. He committed to Oregon St. and turned a first-team All-American honor into a first-round selection by the Red Sox in 2005.

From the very first time he stepped onto a professional baseball field, Ellsbury was one of the best base stealers out there. He stole 23 bases in 35 games in 2005, 41 more in 2006, and another 41 in 2007 before getting called up at midseason.

On top of this, Ellsbury was a skilled hitter, albeit one with very little power, posting at least a .298 average at every level of the minors, and that streak would continue upon his arrival in Boston. Ellsbury hit an outstanding .353 in 33 games, a mark that was so good that he earned a spot on the postseason roster and hit .438 in the team’s series sweep of the Rockies.

Like Buccholz, Ellsbury’s career would be defined by what he wasn’t rather than what he was. His 2011 was an all-time season, a 30-30, .321/.376/.552 monster that would have won MVP if not for an even more historic Justin Verlander effort.

In his other six seasons with the Red Sox, however, he never hit double-digit home runs or match any of those triple slash numbers. That season was also sandwiched between two seasons where he played a combined 92 games.

Those injuries would be a major reason why the Red Sox felt comfortable letting Ellsbury sign with the Yankees, and that proved to be a wise decision. Ellsbury’s speed quickly faded, and the injuries eventually became too much.

He would play just four out of the seven seasons on his contract and somehow is now more unpopular among Yankees fans than Red Sox fans. Go figure. In a fun turn of events, he showed up at Fenway Park last season in his old Red Sox jersey as a part of Dustin Pedroia’s retirement celebration. The opponent watching from the other dugout? The Yankees.

Red Sox SS Xander Bogaerts

The story of how Xander Bogaerts joined the Red Sox seems like something out of a fairytale. According to Alex Speier’s book “Homegrown,” a scout named Mike Lord came to Aruba and after seeing a group of players work out, including Xander’s twin brother Jair, asked if there was anybody else he needed to see. All the players gave the same answer: Xander Bogaerts, who was bedridden with chicken pox.

After some convincing to Xander’s mother, Bogaerts arrived at the field and put on such a show that the Red Sox VP of International Scouting flew in to watch him play. Even after weeks in bed and on an uneven Aruban field, Boogey wowed the Red Sox with his smooth fielding and incredible opposite-field power. Bogaerts would eventually sign with the Red Sox for $410,000, a deal that would go down as one of the greatest in Red Sox history.

Despite playing his first game in the Red Sox organization at 17 and being the youngest player at just about every level, Bogaerts rocketed through the system. He appeared in the 2012 Futures Game and entered the 2013 season as the sixth-ranked prospect in all of baseball.

He was rushed to the big leagues after just 139 games above Single-A, and actually started a number of games during the postseason. He was given the starting shortstop job for the 2014 season, and the hype surrounding him could not have been higher.

Yet even for a player as talented as Bogaerts, progress is not always linear. Xander was so bad at the beginning of 2014 that the Red Sox brought back Stephen Drew to push Bogaerts back to this base. He was undoubtedly better in 2015 (.320 average), but he displayed none of the power that he had become so famous for as a prospect.

It looked like he was putting it all together in 2016, earning an All-Star nod for the first time, but he fell off in the second half. 2017 was a disaster, as he battled through a wrist injury to post a measly .746 OPS.

It was in 2018 that Bogaerts started becoming a franchise icon. Over the past five years, Bogey has slashed .302/.375/.517 (134 OPS+) and averaged 28 home runs and 103 RBI per 162 games. The X-Man entered the league with expectations of greatness, and after an up-and-down start, he has more than met the mark.

Red Sox RF Mookie Betts

It’s hard to believe that there was ever a time that Mookie Betts struggled with the game of baseball, but that was the case in early 2013. An unheralded fifth-round pick out of high school in 2011, Betts displayed good bat-to-ball skills, speed, and defense, but hit just .267 in his first year in the minors with zero home runs. Betts then began the 2013 season batting .145 through May 5, a mark so bad that he began to think about quitting baseball.

It took an intervention by hitting coach U.L. Washington to make the Mookie Betts we know today. Washington realized that Mookie’s big leg kick was throwing off his timing and prevented him from driving the ball with any authority. As soon as the change was made, Betts became a different hitter.

He rocketed up prospect charts by hitting .314/.417/.507 with 15 home runs and 38 stolen bases during that 2013season.  He was even better in 2014 (.346/.431/.529), so good in fact, that he earned a callup to the show at 21 years old.

It’s safe to say that Mookie was worth the hype. Over his six seasons in Boston, he made four All-Star teams, finished in the top 10 in MVP voting four times having won the honor once, while adding four Gold Gloves.

Pretty much the only disappointing thing about Bett’s Red Sox tenure is how it ended: A disheartening trade to the Dodgers in an effort to clear up salary. Despite the abrupt end, however, there is no doubt that Mookie is one of the greatest players in franchise history.

Red Sox LF Andrew Benintendi

After a last-place finish in 2014, the Red Sox had a top 7 pick in the MLB draft for only the third time since 1965. The previous two picks were about as different as you can get. In 1993, the Red Sox selected Trot Nixon, a high school outfielder out of New Hanover who would become a fan favorite and World Series Champion during his decade in Boston. The Sox again had the seventh pick in 2012 and they selected Trey Ball, a high school lefty who never made it to the show.

In 2015, the Red Sox would again go the outfielder route, taking Arkansas’ Andrew Benintendi. Despite standing at just 5’9 and 180 pounds, Benintendi had emerged as the best hitter in college baseball, batting .380 with 19 home runs in the stacked SEC and taking home the Golden Spikes Award.

Benny kept right on hitting upon his arrival to the Red Sox system, showing such an advanced approach that they had him bypass Triple-A and arrive in Boston just over a year after getting drafted.

It’s not that Benintendi has been bad at the major league level. It’s just that he hasn’t been as the once-in-a-generation hitter he appeared to be in the minor leagues. If I told you back then Benintendi would have a .758 OPS from his age 24-27 seasons, you would not have believed me.

So what went wrong with a guy who scouts raved about having a perfect swing? For one, I believe Benintendi sold out too much for power. He put on weight and tried to add more loft to his swing in 2019, and he lost the all-field approach that made him so special.

He’s begun to recapture that a bit in Kansas City, but playing in such a cavernous park prevents him from ever hitting for average power. Benintendi has made himself into a fine player, a decent hitter, and a Gold-Glove level defender. But a perennial .300 hitter with 20 home run power? Probably not.

Red Sox 3B Yoan Moncada

Robinson Cano with more power. That was the scouting report on Yoan Moncada when he entered the Red Sox system as a 19-year-old international free agent. Nobody had ever seen anything quite like him: A 6-2, 225-pound beast who had a sweet swing from both sides of the plate, light tower power, and top-grade speed.

It took the Red Sox $63 million to outbid a number of other teams, an unprecedented amount for a player who never stepped foot on a major league field. Moncada was so good that many of the teams that bid on his services wanted him to report straight to the major leagues, but the Red Sox started Moncada in Single-A. It was almost comical how overqualified he was at the minor league level.

He stole 49 bases in 52 tries in Greenville, then stole 45 bases and hit 15 home runs to kick off 2016 in High-A Salem, and more than held his own as a 21-year-old in Portland (.277/.379/.531). Like Benintendi, Moncada was deemed a once-in-a-generation prospect, otherworldly enough to bypass Triple-A and join the Red Sox as a September callup.

It was in this cup of coffee where Moncada would face his first real struggles and completely alter his future with the Red Sox. After collecting four hits in his first ten MLB at-bats, Moncada struck out in his next nine at-bats and made such a costly mistake on the bases that he was basically unused as the Red Sox pushed for the postseason.

That stretch would change the mind of general manager Dave Dombrowski. Once considered untouchable, Moncada could now be moved if the right player was available, and that player would be Chris Sale. When the  White Sox put their ace left-hander on the trade block, Dombrowski used a package centered around Moncada to outbid all other offers.

More than any other player on the list, Moncada has not lived up to the expectations. He’s struggled with injuries and ineffectiveness, and besides a BABIP-induced surge in 2019, has been pretty much an average hitter throughout his career.

He’s topped 20 home runs just once and has shown little of the speed that made him so dominant in the minors (He’s attempted just five steals in the last three years!). He’s still just 27 and has exhibited good plate discipline and defense, but expecting him to be the five-tool star he was in Greenville half a decade ago is a fool’s errand.

Red Sox 3B Rafael Devers

The world of projecting MLB prospects is a depressing one. In basketball or football, you can watch a college player and see skills that would translate right away to the pro level. Baseball is not like that. It takes years of development, going from minor league affiliate to minor league affiliate before finally reaching the highest level.

That process wipes out countless players, whether through the inability to adjust to more advanced pitching and hitting or through injuries that prevent a player from getting much-needed development time. The hit rate on international players is even lower.

Those players can sign with a major league team as early as 16 years old, meaning it could take them half a decade to climb from the Dominican Summer League all the way to pro ball. Simply put, the player that scouts see during their international trips are rarely the ones you see at the major league level. That’s what makes Rafael Devers so special.

Like Bogaerts, Devers was pretty much the youngest player at every level he played at, but he was never close to being overwhelmed.  He hit .322 as a 17-year-old in rookie ball, hit .288 as an 18-year-old in A ball, and hit .282 as a 19-year in High-A.

The Red Sox were determined not to rush Devers to the majors, but he forced his hand in 2017. He earned a promotion to Triple-A by slashing .311/.377/.578 in Portland, and, after homering twice in his first nine games, was brought to Boston to spark a struggling offense.

Devers was clearly major league ready by the time he made his debut, but he kept making improvements to his game to elevate himself to superstar status. He improved his conditioning to stay on the field more and has missed just 17 games over the last four seasons.

He’s gotten a lot better against lefties and upped his batting average versus southpaws from .229 in 2018 to .333 this season. He’s cut his strikeout rate by nearly 9% from his rookie season and even upgraded his much-maligned defense from disastrous to passable.

The only question remaining for Devers is how long he will be in Boston. The 24-year-old will be a free agent at the end of the 2023 season, and will likely garner a contract upwards of $300 million. As Devers continues to get better and is just now entering his prime, he looks like a sure bet to be well worth the investment.