Boston Red Sox: A look at the top 10 all time 1st round picks

BOSTON, MA - OCTOBER 09: Former Boston Red Sox player Jim Rice acknowledges the crowd before throwing out the ceremonial first pitch before game four of the American League Division Series between the Houston Astros and the Boston Red Sox at Fenway Park on October 9, 2017 in Boston, Massachusetts. (Photo by Elsa/Getty Images)
BOSTON, MA - OCTOBER 09: Former Boston Red Sox player Jim Rice acknowledges the crowd before throwing out the ceremonial first pitch before game four of the American League Division Series between the Houston Astros and the Boston Red Sox at Fenway Park on October 9, 2017 in Boston, Massachusetts. (Photo by Elsa/Getty Images)
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BOSTON, MA – OCTOBER 09: Former Boston Red Sox player Jim Rice acknowledges the crowd before throwing out the ceremonial first pitch before game four of the American League Division Series between the Houston Astros and the Boston Red Sox at Fenway Park on October 9, 2017 in Boston, Massachusetts. (Photo by Elsa/Getty Images)
BOSTON, MA – OCTOBER 09: Former Boston Red Sox player Jim Rice acknowledges the crowd before throwing out the ceremonial first pitch before game four of the American League Division Series between the Houston Astros and the Boston Red Sox at Fenway Park on October 9, 2017 in Boston, Massachusetts. (Photo by Elsa/Getty Images) /

It’s draft day 2018! So what better day to look back and see what successes the Red Sox have had in the first round throughout their history?

With the major league draft kicking off at 7PM tonight, this seemed like a good time to take a look back. We’re going to rank the top 10 all time first round picks for the Boston Red Sox. This list will include Baseball Reference’s verson of WAR, but it will not be the determining factor. And since compensation picks have, historically, technically been considered part of the first round, they will be included in this look.

One of the things this list will tell you is that the best players don’t always come from the first round. Plenty of them do, of course, but you can find very high quality players later in the draft as well. Fred Lynn, Jon Lester and Dustin Pedroia were all second round picks. Mike Greenwell was picked in the third. Jeff Bagwell went in the fourth round of the 1989 draft. Jonathan Papelbon was in the fourth 14 years later. Dwight Evans and Mookie Betts were both fifth round picks! So there’s plenty of reason to pay attention beyond the first. Or even the end of the night which takes us through two competitive balance rounds and the second round as well.

And for those wondering if he got missed in the preceding paragraph, Wade Boggs was selected in the 7th round of the 1976 draft.

The nuts and bolts…

When looking at players drafted in the first round, we will be using several criteria to determine where they fall. And some of the players listed are still playing. It’s possible their placement could shift given more time. Not every player listed here will be popular with Boston Red Sox fans. But that’s okay. We’re looking for the best first round picks. Not the most endearing to fans.

And there were a number of players who just missed the list. Jackie Bradley Jr.’s 2016 season, in which he earned 5.5 rWAR forced some consideration. David Murphy earned a similar amount of rWAR for over his career. He was also an important piece of a few playoff runs in Texas. Scott Hatteberg had a long career and was mostly a productive player. Even Daniel Bard was worth thinking about for the sheer dominance he put on display in 2010. But in the end, these are the ten that made the cut.

Next: #9, 10

Oakland Athletics’ Jed Lowrie follows through on an RBI single in the eighth inning to score Dustin Fowler from second against the Kansas City Royals on Sunday, June 3, 2018, at Kauffman Stadium in Kansas City, Mo. (John Sleezer/Kansas City Star/TNS via Getty Images)
Oakland Athletics’ Jed Lowrie follows through on an RBI single in the eighth inning to score Dustin Fowler from second against the Kansas City Royals on Sunday, June 3, 2018, at Kauffman Stadium in Kansas City, Mo. (John Sleezer/Kansas City Star/TNS via Getty Images) /

All Time Red Sox Draft Pick #10. Jed Lowrie: 15.1 rWAR

Drafted 45th overall in the 2005 draft, Jed Lowrie had a rocky start to his career with the Boston Red Sox. He cracked the majors in 2008 and was a bit below average half a season’s worth of games. He struggled mightily in 2009 over 32 contests. And then looked incredible with a 144 wRC+ in 55 in 2010. It looked like he’d finally busted out. But more than a half season’s worth of struggles in 2011, and a lack of a clear place for him to play led to his being traded to the Houston Astros in a package for Mark Melancon.

That’s also when he started hitting. A 110 wRC+ that year was followed by a 120 the next in Oakland. It was also his first fully healthy season with 154 games played. He would struggle with injuries the next three seasons, and hit near or below league average in each of them. Then he had another healthy season in 2017. He played in 153 games and finished the year with a 119 wRC+ and 14 HR. This season he has exploded out of the gate with a 132 wRC+ and 9 HR in 59 games. He has amassed 2.3 rWAR already. At just 34 years old, he may have a few more productive years in him and could certainly pass the next guy on the list.

All Time Red Sox Draft Pick #9. Clay Buchholz: 15.9 rWAR

This one might be a bit controversial. Clay Buchholz didn’t leave Boston on good terms. He was worth so little at the time that he brought back just Josh Tobias in a trade. Who is Josh Tobias, you ask? Exactly. But the often beleaguered righty actually had some huge moments for the Red Sox. He looked like the team’s next ace when he opened his career with a quality start followed by a no hitter.

He was drafted 42nd overall in the 2005 draft, having fallen from the top of the round due to an incident involving the theft of some laptops. His ceiling was enormous. Unfortunately, he never quite put it all together and struggled with injuries. Often to the dismay of fans eager to see him figure it out. There was no better example of this than his 2013 season. He started the year 9-0 with a 1.71 ERA.

Would the real Clay Buchholz please stand up?

Then he landed on the DL with a neck strain suffered while holding his infant son at night. While certainly a real injury, it was exactly the kind of injury that fueled speculation that he was a “soft” player who didn’t really want to be out on the mound. Such assumptions are tough to quantify, but such is the nature of fandom.

While not much help during the first two rounds of the playoff run in 2013, his hot start did help the team secure the division. And he went 4 IP with no runs allowed in his one WS appearance. He also had a solid but not spectacular start in the 2009 playoffs, going 5 IP and allowing just 2 ER. Clay Buchholz had the talent to land much higher on this list. That is the driving force in the frustration fans feel over him. He is currently pitching for the Arizona Diamondbacks and has a 1.50 ERA over 3 starts. We’ll see if he can keep it up. Regardless, what the Red Sox got out of him, while underwhelming, still makes this a good pick.

Next: #7, 8

NEW YORK, NY – SEPTEMBER 18: Jacoby Ellsbury
NEW YORK, NY – SEPTEMBER 18: Jacoby Ellsbury /

All Time Red Sox Draft Pick #8. Aaron Sele: 20.1 rWAR

Aaron Sele was drafted with the 23rd pick in 1991 as a big right hander out of Washington State University. He had a pitcher’s frame, at 6’3 and would reach the majors just two seasons later. His first two seasons were incredibly encouraging. At ages 23 and 24 he posted ERAs of 2.74 and 3.83. He amassed 7.6 of his career 20.1 rWAR between them. He would spend most of the 1995 season recovering from a shoulder injury, and came back in 1996 with all the hope in the world.

Unfortunately, despite posting his second best FIP in the majors to that point, the results weren’t there. A 5.32 ERA was followed by a 5.38 in 1997 and his Red Sox career would come crashing to an end. Sele would go on to have productive seasons for the Texas Rangers and the Seattle Mariners. But they were surrounded by more poor results. What was once a budding ace would finish his career as an exactly league average pitcher. He retired with a 100 ERA+ over 15 seasons. That’s a solid career, to be sure, but like Clay Buchholz, the promise was for so much more.

All Time Red Sox Draft Pick #7. Jacoby Ellsbury: 31.0 rWAR

This will be another controversial inclusion. Ellsbury bailed on the Red Sox in free agency. He signed a mega-deal with the rival New York Yankees following the 2013 season. It helps that that deal hasn’t worked out for the Bronx Bombers, but the sting is still there. Ellsbury was drafted 23rd overall in 2005. With stories of him running down a deer on foot preceding him, the expectations were extremely high. And he didn’t disappoint in his debut. With a 136 wRC+ in 2007, and his contributions to a championship that year, fans were all in on him.

But like Clay Buchholz, difficulty with injuries and inconsistent play held him back early on. The defense was mostly excellent, though his arm left many cold. It wasn’t Johnny Damon bad, but it wasn’t good. It wasn’t until 2011 that he appeared to tap into his full potential. That season he managed a 150 wRC+, blasted 32 HR and swiped 39 bags. This was the Jacoby Ellsbury Red Sox fans had been waiting for. In fact, he earned more than a third of his career rWAR (to date) that season with 8.3.

That was the apex.

Injuries derailed his 2012 campaign. He returned in 2013 with his power looking more like what we’d seen earlier in his career. Ellsbury hit just 9 HR in 134 games, but stole a mind boggling 52 bases. If this was who he really was, Red Sox fans would have been thrilled. When he signed with the Yankees that winter, many lamented the loss. Jackie Bradley Jr. was an exciting prospect, but he lacked the game changing speed, and Ellsbury was a hard act to follow.

Of course, Bradley has outperformed Ellsbury since then. The former Oregon State outfielder has just 9.9 rWAR since the end of the 2013 season. And he hasn’t played yet this year. While he could still play a few more seasons, the chances that Ellsbury does much to alter his ranking here are low. His rWAR total is higher than the next two players. But with such a huge chunk of it tied up in one season, it’s hard to place him higher.

Next: #5, 6

Jul 08, 2006; Chicago, IL, USA; Boston Red Sox Kevin Youkilis, Trot Nixon, Mark Loretta against Chicago White Sox at the U.S. Cellular Field. The Red Sox won 9-6. (Photo by Matthew Kutz/Sporting News via Getty Images)
Jul 08, 2006; Chicago, IL, USA; Boston Red Sox Kevin Youkilis, Trot Nixon, Mark Loretta against Chicago White Sox at the U.S. Cellular Field. The Red Sox won 9-6. (Photo by Matthew Kutz/Sporting News via Getty Images) /

All Time Red Sox Draft Pick #6. Trot Nixon: 21.3 rWAR

As far as popularity goes, this guy is pretty far toward the positive end of the spectrum. Like a latter entry on this list, Nixon was drafted 7th overall. That was back in 1993. Christopher Trotman Nixon would spend 10 years with the Red Sox. He earned nearly all of his positive rWAR there with 22.4. And he was an above average hitter in all but his debut. That debut season was just 13 games, by the way.

Trot Nixon developed a reputation as a “dirt dog.” Someone who wasn’t afraid to get his uniform dirty. Someone who ground it out every night. Someone who “cared.” His name would be invoked by fans a few years after he departed to ride high priced free agent J.D. Drew. Drew rarely came off the field at the end of the night with grass or dirt stains on his jersey. Of course, Drew was a significantly better defender who rarely needed to dive. But that’s another article for another time. That said, his combination of raw production and his popularity, not to mention his role in the 2004 curse-breaking title run land him at number 6 on our list.

All Time Red Sox Draft Pick #5. Andrew Benintendi 4.6 rWAR

I’m probably going to get some flak over this, but yeah, I’m going with Andrew Benintendi. This is the other number 7 overall pick (in 2015) I alluded to earlier in the article. And yes, it’s way too early to be predicting where he will finish in an all time list. But I don’t care. This is a kid who made it to the majors just a year after being drafted as a sophomore. He played for the University of Arkansas and has done nothing but mash since graduating high school.

Arriving in late 2016, Andrew Benintendi finished that season with a 122 wRC+ over 34 games. He then followed it up with a full rookie campaign in which he hit 20 HR and had 20 SB. His wRC+ was just 103. But the tools that got him drafted were on full display. So far this year he has a 143 wRC+ with 9 HR and 9 SB. So the ratios are still in place, but his walk rate is up and he’s attacking pitches in the zone more frequently. That’s visible with an increase in zone swing percentage of 5.6%. He’s also cut his soft contact percentage down by nearly 8% while allowing himself to not rely entirely on pulled balls for his power.

The power surge is a sign of growth.

He has improved his SLG on balls to center field by .075 and his wRC+ from 107 to 147. Being able to drive the ball somewhere other than the pull side, when playing half his games in Fenway Park with its massive right field has done wonders for his production. He still crushes the ball to the pull side, of course, with a 171 wRC+ this year compared to a 164 last year. That’s especially true on fly balls where those numbers go from 383 last season to 530 this year.

So yeah, it’s jumping the gun to rank Andrew Benintendi this high. But so what? The tools are clearly there. At this point, the one factor that could derail him is injury. But if what we’re seeing this season is an accurate representation of who he is, he’ll pass Nixon in rWAR well before he even has a chance to hit free agency. He may even pass the next guy.

Next: #3, 4

Dec 17, 2007 – New York, New York, USA – MO VAUGHN is one of 89 players named in the Mitchell Commission report on steroid use in Major League Baseball. PICTURED: A portrait of Boston Red Sox first Baseman Mo Vaughn taken on Sep. 27, 1996 in Boston (Photo by Sporting News/Sporting News via Getty Images)
Dec 17, 2007 – New York, New York, USA – MO VAUGHN is one of 89 players named in the Mitchell Commission report on steroid use in Major League Baseball. PICTURED: A portrait of Boston Red Sox first Baseman Mo Vaughn taken on Sep. 27, 1996 in Boston (Photo by Sporting News/Sporting News via Getty Images) /

All Time Red Sox Draft Pick #4. Mo Vaughn: 27.2 rWAR

Yet another 23rd overall pick, Mo Vaughn was David Ortiz before David Ortiz had stopped calling himself David Arias. A big bodied left handed slugger that was at home in the heart of an order, Mo Vaughn blasted 29 or more home runs in five out of six season with the Red Sox between 1993 and 1998. The one season he did not was shortened by injury. And he hit 26 over 111 games that year. He was a monster at the plate with wRC+’s between 134 and 151 in each of those seasons.

The team elected not to resign him following the 1998 season and he caught on with the Anaheim Angels. While his overall production took a step back, the home run power was still there. He had a 114 wRC+ with 36 HR in 1999. Then a 115 wRC+ with 66 HR in 2000. He would miss all of 2001 with an injury, and was never quite the same after that. But for the first 10 years of his career, few hitters were more feared. He even won an MVP award in 1995.

The end came quickly.

His career would end following the 2003 season after a series of ankle and leg injuries at the age of 35. This was at a time when players were pushing into their late thirties and sometimes their early 40’s before seriously declining. Had his body not failed him, he may have had a shot at the Hall of Fame. But no matter what else we remember about him, he was an absolute titan at the plate during his prime. So we’ll leave you with this Mets highlight where he hit a ball more than 500 feet.

All Time Red Sox Draft Pick #3. Nomar Garciaparra: 44.2 rWAR

Now we’re getting to some interesting players. Nomar Garciaparra may not have left the Red Sox on the best terms, but there’s no arguing against his placement on this list. There was a point in the late 90’s where there was a serious question about who the best shortstop out of Nomar, Derek Jeter and Alex Rodriguez was. Okay, fine. It was mostly about who was second best behind ARod. But given where their careers ended up, it’s kind of nuts to look back and think about Garciaparra in those terms.

But he was certainly right there, and perhaps was even out to an early lead with rRC+’s of 122, 139, 157 and 154 in his first four full seasons. He finished that 2000 season with 117 career home runs. But that’s when his first injury plagued season happened. He came back and had two full seasons in 2002 and 2003, but the bat wasn’t quite the same.

The beginning of the end.

Nomar then missed most of the first half of the 2004 season before being traded to the Cubs at the deadline. He never did recapture the glory of his youth, but with a rookie of the year award in 1996 and a runner up for the MVP in 1997, the dreams of what might have been are still had across New England to this day.

He would finish his career with 6 All Star game appearances, 5 top ten finishes in MVP voting, 229 HR and a career 124 wRC+ He won two batting titles and a Silver Slugger.

Next: #1, 2

WICHITA, KS – AUGUST 10: Roger Clemens, wearing his Red Sox jersey, pitches with the Kansas Stars, a team made up of almost all retired major leaguers, playing in the NBC World Series against amateurs at Lawrence-Dumont Stadium in Wichita, Kansas, Aug. 10, 2016. (Photo by Stan Grossfeld/The Boston Globe via Getty Images)
WICHITA, KS – AUGUST 10: Roger Clemens, wearing his Red Sox jersey, pitches with the Kansas Stars, a team made up of almost all retired major leaguers, playing in the NBC World Series against amateurs at Lawrence-Dumont Stadium in Wichita, Kansas, Aug. 10, 2016. (Photo by Stan Grossfeld/The Boston Globe via Getty Images) /

All Time Red Sox Draft Pick #2. Jim Rice: 47.7 rWAR

And that brings us to the first Hall of Fame caliber player to be drafted in the first round by the Red Sox. Jim Rice is basically Mo Vaughn with better health and more longevity. His bat was one of the most feared in all of baseball. He smashed 382 career home runs, 373 doubles, and finished with a career .853 OPS in 16 major league seasons. He needed every last year of eligibility to get in, with just 76.4% of the vote, but he got there.

Jim Rice had four seasons with a wRC+ greater than 140 and at least 39 HR. He hit 20 or more in 7 others. The Hall of Fame outfielder and DH spent his entire career with the Red Sox and currently appears as an analyst for NESN in pre and post game coverage. He made 8 All Star games and won the Silver Slugger twice. His number 14 is hanging in Fenway Park, never to be worn by a Red Sox player again. There’s really not a lot to say about Rice. He’s clearly number 2 on this list until someone unseats him. And as high as I am on Benintendi (above), that’s not a bet I’m willing to make.

All Time Red Sox Draft Pick #1. Roger Clemens: 139.0 rWAR

Bring out the pitchforks. Rarely has a player performed so well for a team and become so vilified by them after departing. Roger Clemens is the clear choice for the all time best first round pick by the Red Sox and it’s not particularly close. The Rocket should already be in the Hall of Fame, but steroid allegations have delayed his entry. He has an MVP award, 7 Cy Youngs, 7 ERA titles, and an All Star game MVP to go along with 11 appearances at the Midsummer Classic. He finished his career with 4,672 strikeouts and 354 Wins. While Wins are an outdated metric, 354 is still a Herculean feat.

On top of the 7 Cy Young awards, he finished in the top 10 five other times. He is one of the greatest starting pitchers to ever toe the rubber. No amount of PED accusations or mercenary labels will change that. His postseason record wasn’t quite so spotless. But a 3.75 ERA over 199 innings with 173 strikeouts and a 12-8 record is nothing to sneeze at. He ranks 3rd all time for pitchers in rWAR, and 1st for Cy Young career shares. His win total is 9th most all time, and that strikeout total is 3rd. No one has more complete games than him.

The HoF is all but inevitable.

In his 6th year on the ballot, Clemens finished with the 7th highest percentage of votes at 57.3%. It seems inevitable that he’ll eventually get in, despite the allegations. Unlike some candidates, he’s mostly kept out of the public consciousness and seen his percentage tick up steadily recently. Time heals all wounds, right? As he gets further from his playing days, nostalgia for what he did on the mound will outstrip resentment over perceived steroid use. It might take every year of his eligibility, but I’d be very surprised if we don’t see him in Cooperstown.

Next: Red Sox names to consider on day one of 2018 draft

If you enjoyed this look at the past, how about a look ahead? While you wait for draft coverage to kick off at 6 PM tonight we have more content for you. Check out this full preview of the Red Sox and their first round options!

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