Touching All the Bases

Top 50 Red Sox Prospects of the Past 50 Years: Introduction, Or Hello Again, Juan Bustabad


In the interim — after Grady Sizemore established himself as a five-tool superstar in Cleveland but before his Ft. Myers-to-Boston resurrection this spring — the Red Sox were thought to have had a Grady Sizemore of their own.

That is to whom Ryan Westmoreland was compared by Baseball America in 2010. He was ranked as the No. 1 prospect in the Red Sox organization that spring, and 21st overall in baseball, one spot ahead of Reds phenom Aroldis Chapman. It was heady company and high praise, and it was deserved.

In his first season of pro ball, as a 19-year-old at Single A Lowell, the native New Englander and proud son of Portsmouth, Rhode Island hit .296/.401/.484 with 7 home runs in 267 plate appearances. He walked nearly as often as he struck out, played graceful defense (at least before breaking his collarbone crashing into a wall that August), and stole 19 bases without getting caught. According to the 2010 Baseball America Prospect Handbook, Jason McLeod, then the Red Sox’ farm director, said Westmoreland had more upside than any player the club selected in his five years running the drafts.

Portsmouth High is 62.5 miles from Fenway. LeLacheur Park in Lowell is 31.2 miles from 4 Yawkey Way. But Westmoreland’s ability — “his skills are just as impressive as his considerable tools,” Baseball America praised — suggested his journey to the big leagues would be a similarly short one.
Instead, it was his career that was short. Westmoreland suffered bleeding on his brain during 2010 spring training, the result of a previously undetected cavernous malformation, an ominous term that became all too familiar.
A hopeful attempt to return to baseball was cut short by a setback that required further brain surgery. Westmoreland announced his retirement on March 6, 2013. He was 22 years old, his baseball career limited to that single, sunny 60-game season in Lowell.
I hope he remembers every joyous moment from every inning he played, savoring the season he got to have rather than those that were taken away.
I lead off with an acknowledgement of Westmoreland here for one reason. He was the most difficult omission from this long-curated project — the top 50 Red Sox prospects in 50 years of the amateur draft era.
His promise was so vast, but because his time in professional baseball was so brief, he didn’t quite make the cut. In my mind, he’s No. 51 on this list, with a proper and due homage. But in truth, there are so many other prospects who could stake a claim to being the most glaring omission.
Before we get to counting down who made it — Nos. 50-41 will run later today. With at least one group of 10 players running each day forward through Friday, you’ll see the likes of phenoms Carlton Fisk ….



… and Roger Clemens along the way …
…. let’s tip our cap to a few who didn’t make it. Right after a Sam Horn-quick word on the reasoning, process and inspiration.
As I’ve mentioned here probably to the point of annoyance, I fell for the Red Sox as an 8-year-old during the 1978 season. Despite how that ended, the buildup to the Game 163 sadness was entertaining and joyous enough that I was hooked for life despite, you know, Zimmer and Bucky F. Dent and all that.
The fledgling love for baseball was fed by a series of related factors that obviously have a lot to do with me being right here, right now, today.
My dad loved the Red Sox. My dad, upon arriving home from work every day, would have The Boston Globe tucked under his arm so he could read about the Red Sox. The writer he was reading more often than not was Peter Gammons. I’m grateful for that lineage.
Following prospects nowadays is a conventional part of following baseball. We knew about the promise of Xander Bogaerts before he took a swing Double A. His ascent and the obvious question — where does he rank among the all-time best Sox prospects? — was a smaller impetus for this.
So too was the chance to commemorate the 50th anniversary of the amateur draft, which began with the Kansas City A’s selection of Rick Monday in 1965. That is why there is no Ted Williams or Babe Ruth on this list, no Tony C. or Dom DiMaggio, no George Scott or Reggie Smith. They all pre-dated the draft, and thank goodness. Trying to gauge the Red Sox finest prospects in those long-gone eras is a task for someone even more addled with baseball nostalgia than yours truly. In fact, it’s impossible.
But now? The information is available, and the only limit is the saturation point of your interest. Even the amateur draft, which features a relatively high miss-rate for even first round picks and doesn’t offer the instant gratification of the NBA or NFL drafts, is televised these days. We familiarize ourselves with kids who may never make the majors, and who may never be above replacement-level if they do.
Why? Because following the path of a promising prospect — of having the bragging rights that you identified your team’s future star first — is a fun sidelight to following the day-in, day-out happenings of the major league team. And when I was that child of the ’70s — and the early ’80s, and straight on into my permanently delayed adolescence now — no one was writing about prospects to the degree Gammons was for the Globe.
There were many great joys in pulling together this project, which I began working on during any downtime of more than moment or two pretty much after I devoured this initial piece of ah-ha inspiration: David Schoenfield’s terrific 2011 piece for ESPN on the 50 best prospects of the draft era.
But there was no greater joy than digging through the Boston Globe archives — especially the treasure trove of photos and clips still to be found in the ancient subterranean library at the far end of the newsroom — to find insightful early references to players who were in consideration for this list.
The byline on these stories, even as seasons turned to decades and one-time prospects became big-league veterans if they were so fortunate — was the name Peter Gammons, and perhaps even more often than you would imagine. A debt of gratitude is owed to him from this address, not just for inspiring me with my dad and the daily newspaper as the conduits, but for what he and how wrote.
Not just about those who made it big, but for so many who didn’t. In the spirit of the project, a couple of the more hyped Gammons favorites from the ’80s made the back end of countdown. You simply cannot have this list without Juan Bustabad, you know.
Just because it feels right, here are some scattered Gammons snippets through the years on a few who made it barely beyond the big league fringe if they ever got that far. I could give you dates. But I won’t. These write-ups, and this homage, is timeless:
Let there be no doubt about one thing: Everyone in the Carolina League knows [Jackie] Gutierrez. You see, all the time he is in the field, he is whistling. Sometimes it’s just a few shrill notes of encouragement, sometimes a few shrill notes of recognition. This season, he’s added a few full tunes to his repertoire. “Funky Town” is a big favorite. So is “Here Comes The Bride …
Both Morgan and scouts like 24- year outfielder Gene Gentile, a smaller edition of Fred Lynn. He had to DH most of the year because of a spring training elbow injury, but he is a good defensive outfielder with a live bat …
Steve Crawford is a stud. He is a big, strong horse out of Oklahoma who might have been rushed in 1981 before his bone spur operation, but he’s a tough kid (remember how he drilled Carlton Fisk last April) who trains with Tom Burgmeier. And once he gets his arm back – be patient, that might take an entire season – he may well be a 250-inning, 18- to 20-win staff saver …
Skinny Californian Jeff Sellers, who looks as if he should be the guitarist for The Fixx, also won 12 games, as did former Michigan State quarterback John Leister. In fact, Leister, who has done very little pitching, threw one-, three- and four-hit shutouts in his last three starts.
The Globe archive — the Gammons archive — was a source of immeasurable value. I might call it the definition of a labor of love, if only I could figure out what part was supposed to be the labor.
The Globe archive wasn’t the only essential resource. For more recent prospects, the Baseball America Prospect Handbooks (beginning in 2001) and the Baseball Prospectus annual (my library begins in 1997) were of immeasurable value. Slightly older information was acquired from various Bill James publications: The legendary Abstracts, as well as the wildly entertaining The Baseball Book and Players Ratings Book annuals from the early and mid ’90s.
The Sports Illustrated Vault, Society of American Baseball Research biographies, the Baseball Hall of Fame’s Diamond Mines archive of scouting reports, and several books — most notably “The Wrong Stuff” by Bill Lee and Dick Lally, Gammons’s “Beyond the Sixth Game,” Howard Bryant’s “Shut Out,” and “The Bottom of the 33rd” by Dan Barry — were extremely helpful. Baseball America’s organizational Top 10 prospect lists dating back to 1983 were a fun way to lose a couple of hours. So were the annual Red Sox media guides, which were more candid in those days. (“Carl, who sure likes his Marlboros, hit 40 round-trippers for the second year in a row …”)
In sorting out the rankings of our 50, of deciding between, say, Bruce Hurst and Jon Lester, or Butch Hobson and Ted Cox, I kept the process simple, like Schoenfield did for his list four years ago. I tried to imagine how prospects from the days before the Internet and Baseball America would be perceived today with all of the information and resources we now have.
How good they became is a small part of the consideration. How good they seemed like they might become is a bigger part. Tools mattered, of course. So did production, but the variables of league and age were factored in. Strikeout-to-walk ratio played a huge role in judging young pitchers. On-base percentage, not always valued in the see-the-ball, hit-the-ball ’70s, was a strong consideration for evaluating batters. There’s no doubt that Wade Boggs, he of the .335/.437/.460 slash line for the 1981 PawSox, would be far better appreciated during his ascent nowadays.
Strength of the organization at the time some prospects were evaluated also mattered. A No. 1-rated prospect such as Seung Song from the Dan Duquette Era of Farm System Neglect did not come close to making this list. With that in mind and the ground rules explained, here are a few names that got consideration for this list but didn’t make the cut, broken down by category:
Former No. 1-ranked Red Sox prospects according to Baseball America’s annual ratings: Lars Anderson (2009), Dernell Stenson (rest in peace — I really tried to include him), Donnie Sadler (ranked ahead of Nomar in 1996), Andy Marte (2006), Seung Song (2002), Steve Lomasney (2000), Daisuke Matsuzaka (2007, shouldn’t have been called a prospect based on his success as professional in Japan), Will Middlebrooks (2012), and Jose Iglesias (2011).
A surprisingly deep collection of catchers: Rich Gedman, Gary Allenson (1978 International League MVP with 20 homers and a .913 OPS), Ernie Whitt, Bo Diaz, Scott Hatteberg, John Marzano, Bob Montgomery (some in the organization thought Monty, not Pudge, was the catcher of the future in the late ’60s), Kelly Shoppach, Lomasney (again), and Dave Schmidt (had a monster season at Bristol in ’79 — .332/.453/.571 with 19 homers).
Pitching prospects who turned suspect: Joel Finch (ruined by Don Zimmer), Bobby Sprowl (ruined by Don Zimmer), Juan Pena (two brilliant starts then gone), Craig Skok, Mark Bomback, Mike Nagy (runner-up for ’69 AL Rookie of the Year walked 106 in 196.2 innings), Jim Burton, Craig Hansen, Al Nipper, Chuck Rainey, Allen Ripley, Kevin Morton (the Abe Alvarez of his time), and Abe Alvarez (the Kevin Morton of his time).


Good to excellent major leaguers who didn’t quite make this cut: John Valentin (wasn’t supposed to be able to hit), Justin Masterson, Jody Reed, Oil Can Boyd, Freddy Sanchez (the best of a lousy Red Sox early 2000s farm system), Adam Everett, Rick Miller (spectacular defense, but hit .250 in the minors), Anibal Sanchez, Tim Naehring, John Tudor (spent two full and two more partial seasons at Pawtucket), Bob Stanley, (in Double A in ’76, he walked 83 and struck out 78), John Curtis, Lynn McGlothen, Mike Garman, Daniel Bard, Jed Lowrie, Brandon Moss, and, pictured, Ben Oglivie (“He was one of those good-looking prospects the Red Sox seemed to come up with every spring. He’d hit line drives all over Winter Haven, the team would bring him north and he’d spend all summer counting spiders in the Red Sox dugout.” — Ray Fitzgerald, 1980).
Assorted others: Jack Baker (one report said he had Frank Howard power), Jeff McNeely, Casey Kelly, Greg Blosser, Wilton Veras (possibly the most overrated prospect of his generation), Reid Nichols (tough omission; 12 homers, 66 steals, and a .798 OPS as a 20-year-old at Winston-Salem in ’79).
Curtis Montague Schilling: He’s more accomplished than all but a half-dozen or so players who did make the cut. He did reach Double A at age 21, but he struck out just 62 against 40 walks in 106 innings before he was traded along with Brady Anderson to the Orioles for Mike Boddicker in July 1988. He never cracked the top 10 prospects in the Red Sox organization according to Baseball America. It took him a long time to become Curt Schilling, Quality Major League Pitcher, let alone Curt Schilling, Mystique and Aura Vanquisher. But he’s No. 52 here … right behind Ryan Westmoreland, of course.
I hope you enjoy reading the countdown — especially some of the stuff on lesser-known phenoms — as much as I did putting it together. I don’t think I missed anyone — current prospects were not included — but you may disagree with the order. That’s cool with me. So here you go: the 50 best Red Sox prospects of the past 50 years. Some became legends. Some never saw the inside of Fenway. But all together and at the least, they make for a heck of a fun baseball argument. So let’s have it already. After all, it is 50 years in the making.

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