Boston Red Sox: Ranking the top 10 players from the 1990s

The Red Sox of the 1990s had some very good teams but weren’t quite good enough. Here’s a list of their ten best players from that decade.

Having been born at the very beginning of 1980, I’ve always considered myself a child of both the 1980s and 1990s. The earlier decade encompassed my elementary school years and I started middle school in 1990. So the latter decade spanned the entirety of my high school and college years and I feel fully a part of both.

Even though the 1980s Red Sox teams are the ones I look back with the most nostalgia when I think about my childhood (especially the 1986 team), I have a lot of good memories of the 1990s teams as well. Like the 80s, the 90s started off with some bad Red Sox teams but by the middle of the decade, they were competitive once again.

The 90s Red Sox had the misfortune of playing during the heyday of the great New York Yankees dynasty that won four World Series between 1996 and 2000. The Cleveland Indians of the decade, who won two pennants and six division titles that decade, also stood in the way of the Red Sox.

Boston made the postseason three times in the 90s (in 1995, 1998, and 1999) and in each case lost before reaching the World Series, only once making it to the ALCS (in 1999). Their teams were very good but not good quite enough, a label that seemed to follow them until they finally broke through and won the World Series in 2004.

However, the teams of the mid-to-late 90s were fun to watch and showcased some great players, many of whom are on the following list. The joy of winning in 2004 eased the angst of the teams from the past that came up short, so let’s just have some fun with this one.

Having just done this list for the best Red Sox players of the 1980s, I knew I had to continue and look at the best from the 1990s. Those two decades encompassed the totality of my first twenty years while, so let’s begin in no particular order.

Roger Clemens

If you’ve read any of my work, you’ll know that I’ve been a huge Roger Clemens fan since 1986 and remain so to this day. Regardless of the PED accusations that have hung over his head the last decade, I believe he deserves to be in Cooperstown. Just his numbers in a Red Sox uniform alone would qualify him, especially with how much the bar for induction has been lowered.

Since Clemens’ twelve-year Red Sox career perfectly straddles the two decades, he’s making both the 1980s and 1990s list. While his numbers from 1984-1990 were better than what he did from 1991-1996, he still belongs on the current list.

Between 1991 and 1996, Clemens compiled the following line: 76-60 W-L, 3.36 ERA, 1166 K, 1263 IP, 1.215 WHIP (177 starts).

While those numbers aren’t as good as what he put up in the 1980s, Clemens did win 18 games in both 1991 and 1992 and had a winning record in four of the six seasons. He did miss time with injuries in 1994 and 1995 but otherwise was his usual workhorse self. He also threw the second twenty-strikeout game of his career in 1996, ten years after throwing his first.

He led the league in ERA in 1991 and 1992, strikeouts in 1991 and 1996, starts in 1991, and WHIP in 1992. His lone postseason appearance for the Red Sox in the decade was in 1995 when they were swept by the eventual American League pennant winners, the Cleveland Indians, in the ALDS.

After the 1996 season, then-GM Dan Duquette made Clemens the largest free-agent offer ever for a Red Sox player while declaring in an often-misquoted statement that the team wanted to keep him in Boston “in the twilight of his career.” Instead, Clemens left in free agency for Toronto before heading to the Yankees, Astros, and back to the Yankees.

Never a great postseason pitcher despite his incredible regular-season numbers, many Red Sox fans hated Clemens after he left and it’s only been in recent years that they’ve softened on him. Still, there’s no denying that he was one of the greatest Red Sox players in both of the decades in which he played for them.

Pedro Martinez

The case of Pedro Martinez is the case of a player who only spent seven seasons out of his 18-year career with the Red Sox. However, it’s inarguable that what Martinez did in those seven seasons in Boston are the reason why he was eventually enshrined in the Baseball Hall of Fame after his retirement.

Then-GM Dan Duquette traded to acquire Pedro from the Montreal Expos after the 1997 season and was instantly rewarded. The Red Sox ended up with the man who became one of, if not the most dominating pitcher of the late 1990s and early 2000s which is even more impressive given that it was the height of the league’s steroid era.

From 1998-2000, Pedro put up the following stats:

1998: 19-7 W-L, 2.89 ERA, 251 K, 67 BB, 233.2 IP, 1.091 WHIP (33 starts)

1999: 23-4 W-L, 2.07 ERA, 313 K, 37 BB, 213.1 IP, .923 WHIP (29 starts)

2000: 18-6 W-L, 1.74 ERA, 284 K, 32 BB, 217.0 IP, .737 WHIP (29 starts)

Look at those numbers…they’re absolutely insane and are three of the greatest seasons any pitcher has had in the history of baseball. Pedro’s 1998 season was fantastic, but it was his 1999 and 2000 seasons that cemented his place as one of the most dominant hurlers of his era. He won the American League Cy Young award both seasons but that only tells part of the story.

In 1999 he had an ERA barely over two and he struck out over 300 batters while only walking 37. Again, this was at the height of the steroid era when guys like Mark McGwire, Barry Bonds, Rafael Palmeiro, Jason Giambi, Sammy Sosa, and others were juicing and hitting a ridiculously inflated number of home runs.

Pedro’s WHIP in 1999 was a gaudy .923, but in 2000 he was even better, lowering it to an almost unfathomable .737, while again striking out almost 300 batters and only walking 32. He also lowered his ERA to 1.74, the lowest in the American League since 1978. To dominate that much when just about every hitter was on steroids and hitting balls out of the park left and right was truly staggering.

Pedro added to his Red Sox legend in 1999 when he struck out five batters in two innings in the All-Star Game, which was played at Fenway Park. Then, in the ALDS against the Cleveland Indians, Pedro was forced to leave his game one start after only a few innings with a back strain. He came back in the deciding fifth game to throw six no-hit innings in relief, whiffing eight and helping the Red Sox move on.

Pedro continued to be great for the Red Sox and was instrumental in helping them finally win the World Series in 2004, but it was his two seasons in the late 1990s that made him a Boston legend. For those who weren’t around to see Pedro pitch, it was an incredible experience. Every one of his starts was an event and the energy in the crowd was electric.

I was fortunate to see Pedro pitch in person multiple times and there was nothing like it. You never knew what incredible thing you were going to see and the excitement was palpable; it even came across when watching the games on television. There was nothing like being at Fenway Park for one of his starts, though, and those games I went to when he pitched are some of my favorite memories.

Nomar Garciaparra

Probably the most obvious player on this list and the one whose inclusion should surprise no one is Nomar Garciaparra. A member of the Holy Trinity of Shortstops in the mid-to-late 1990s, Nomar along with Derek Jeter and Alex Rodriguez helped to revolutionize the position going into the twenty-first century.

Nomar spent the first nine seasons (1996-2004) of his 14-year career with the Red Sox and although injuries started to take their toll on him after 2003, his 1990s seasons are still among the best any Sox shortstop has ever had. Between 1996 and 2000, Nomar put up the following numbers:

.320 BA, 117 HR, 436 RBI, 184 BB, 451 R, .366 OBP, .924 OPS

While Rodriguez hit for more power and was the slickest fielder, Nomar combined hitting for high average with power in a way the Red Sox hadn’t seen since Ted Williams. Like Pedro Martinez, it was Nomar’s 1999 and 2000 seasons that were utterly superlative.

1999: .357 BA, 27 HR, 104 RBI, 51 BB, 103 R, .418 OBP, 1.022 OPS (135 games)

2000: .372 BA, 21 HR, 96 RBI, 61 BB, 104 R, .434 OBP, 1.033 OPS (140 games)

He won the batting title in both of those years and flirted with .400 in 2000, hitting over the mark as far into the season as late July before tailing off. His .372 average was the highest for a right-handed hitter in the post-World War II era and he became the first right-handed hitter in either league to win consecutive batting titles since Joe DiMaggio.

Unfortunately, wrist and leg injuries slowed Nomar down in the early 2000s and while still very good, he was never quite the same. He became famously grumpy and at odds with the Red Sox front office and was eventually traded at the deadline in July 2004, which many think spurred the team as they eventually won the World Series that year.

Regardless of what happened over the remainder of Nomar’s career, his time in Boston in the 1990s as one of the top shortstops and hitters in the game makes him a no-brainer for this list.

Mo Vaughn

One of the Red Sox’s most productive sluggers of the 1990s is now one of their most overlooked stars from that or any decade. Mo Vaughn was a homegrown player who called Boston home for the first eight seasons (1991-1998) of his twelve years in the majors and anchored first base for most of the decade.

“The Hit Dog,” as he was known, put up respectable numbers in 1991 and 1992, but it wasn’t until his third season in 1993 that he made his presence known when he clubbed 29 home runs and drove in 101. From there, he never hit fewer than 25 home runs in a Boston uniform. His stats from 1991 to 1998 look like this:

.297 BA, 230 HR, 752 RBI, 519 BB, 628 R, .387 OBP, .909 OPS

Vaughn was an All-Star in 1995,1996, and 1998 and won the 1995 American League MVP award with a .300 average, 39 home runs, and 126 RBI. While he was very popular with fans, he clashed with Red Sox ownership and the front office and after the 1998 season, he left in free agency for the Anaheim Angels (as they were called at that time).

Vaughn had some success in Anaheim and later New York (Mets) before his career ended, but his ballooning weight and injuries slowed him down. The Red Sox definitely got the best out of Vaughn and he remains one of the best sluggers they’ve ever had over their long history.

John Valentin

John Valentin is one of the more overlooked former Red Sox players, but he was a very good player for a long time. He wasn’t a superstar, but he was a solid contributor to the 90s Red Sox teams and spent all but the final season of his eleven year career, which spanned 1992-2002, in Boston.

Prior to Nomar debuting with the Red Sox in 1996, Valentin was the team’s starting shortstop. In order to make room for Garciaparra, he shifted over to third base for the remainder of his career. He was a solid defender and hitter who put up nice numbers in Boston. During the 1990s in Boston (1992-2000), he put up the following:

.281 BA, 120 HR, 523 RBI, 432 BB, 588 R, .355 OBP, .815 OPS

He had his best season in 1995 when he hit .298 with 27 home runs and 102 RBI and remained productive until injuries caught up to him in 2000. He ended up leaving Boston after the 2001 season and finished his career with the Mets in 2002. From 1992 to 1999, though, Valentin was a durable, productive, and ever-present fixture on the left side of the infield for the Red Sox.

Mike Greenwell

Mark down Mike Greenwell as the only other player on this list who, along with Roger Clemens, also appeared on the 1980s list. Like Clemens, Greenwell’s career neatly straddles the two decades, spanning from 1985 to 1996. While Greenwell’s Red Sox career ended in 1996 like Clemens’ did, that was because having spent his entire career in Boston he retired after the season.

We already went over Greenwell’s 1980s numbers in the previous list, so here we’ll only look at what he did between 1991 and 1996.

.285 BA, 57 HR, 338 RBI, 209 BB, 331 R, .345 OBP, .766 OPS

Those aren’t great numbers and they’re inferior to his 1980s production, but they’re respectable. Greenwell also contended with injuries toward the end of his career which hampered his production. Still, he was, for the most part, a solid and reliable contributor in the 1990s as he was in the 1980s and as a loyal Red Sox career lifer, deserves to be on both lists.

Troy O’Leary

Troy O’Leary spent the majority of his career with the Red Sox, patrolling the outfield with the team from 1995 to 2001. Almost immediately upon his arrival in Boston in 1995, O’Leary became a valuable contributor in the batting order and put up some excellent numbers.

His first season with the Red Sox resulted in a .308 average with 10 home runs and 49 RBI and from there he only got better. His best season in Boston was 1999 when he hit .280 with 28 home runs and 103 RBI.  He was also, along with Pedro Martinez, one of the main reasons the Red Sox reached the ALCS that year.

In the same game that Martinez famously threw six innings of no-hit relief, O’Leary hit a grand slam and a three-run homer in the deciding fifth game of the 1999 ALDS to help the Red Sox eliminate the Cleveland Indians and move on to face the Yankees. Unfortunately, within two years O’Leary was the odd man out in the Red Sox outfield (especially since they signed Manny Ramirez in the winter of 2000).

Still, his excellent hitting combined with his excellent defense (a .984 fielding percentage and only 27 errors committed in Boston) made Troy O’Leary one of the best and most underrated Red Sox of the 1990s.

Tim Wakefield

Tim Wakefield spent seventeen seasons with the Red Sox and retired as their all-time leader in innings pitched and is second place all-time for games won by a Sox pitcher at Fenway Park and third all-time for total games won by a Sox pitcher. A converted second baseman who taught himself how to throw a knuckleball, Wakefield spent the first two seasons of his career with the Pittsburgh Pirates before being released in 1995.

Signing with the Red Sox, he’d go on to pitch both as a starter and a reliever until the end of the 2011 season when he retired at the age of 44. A member of the 2004 and 2007 World Series champions, Wakefield was a valuable member of those teams, but he also contributed significantly to the 1990s Red Sox teams as well.

From 1995 to 2000, Wakefield racked up a 71-65 record with a 4.58 ERA and 762 strikeouts. Keeping in mind that knuckleballers are feast or famine (they’re either unhittable or they’re throwing batting practice), those are respectable numbers. Beyond the stats, Wakefield was a workhorse, appearing in 230 games (with 155 starts).

With the lack of wear and tear on the arm a benefit of throwing the knuckleball, Wakefield gave the Red Sox whatever they needed whether it was out of the rotation or the bullpen. He wasn’t their greatest pitcher, but he was rock solid, at times excellent, and definitely one of their best in the 1990s.

Tony Pena

This one might be an example of a little personal bias seeping in since I’m a former catcher myself, but Tony Pena was probably the Red Sox best catcher in the 1990s until they acquired Jason Varitek in 1997. Pena was a veteran of ten major league seasons before signing with the Red Sox as a free agent after the 1989 season. He only spent four seasons in Boston, from 1990-1993, but made a strong impact.

He had one of his best seasons in 1990 when he led the American League in games played for a catcher with 143 and putouts and finished second in fielding percentage and assists. He had another fine defensive year in 1991 and won a Gold Glove.

He was also well-known for his unique crouch where he stuck one of his legs out and sat on the ground in what looked like a split. (This was imitated by my friends and me when we played Wiffle Ball and even Little League, much to the consternation of our coaches!).

Offensively Pena was decent in Boston, producing a .229 average while hitting 17 home runs and 161 RBI. However, he wasn’t valued for his bat as much as he was his defense behind the plate and for that, Pena was a valuable member of the Red Sox in the 1990s despite his short time in Boston.

Honorable Mentions

This is a group of players who were pretty good for the Red Sox in the 1990s but didn’t quite make the cut. First up is Jody Reed who is a weird case in that he spent the first six years of his career in Boston and straddled both the 1980s and 1990s. From 1987 to 1992 he was a very good shortstop and second baseman.

He hit .280 with 17 home runs and 227 RBI in his Red Sox career and led the American League in doubles in 1990 with 45. He wasn’t good enough for me to put him on the 1980s list and he’s really not good enough to be on this list, but because he was decent enough to merit consideration and played a roughly equal amount in both decades, I thought he deserved inclusion here.

Tom Brunansky was acquired by the Red Sox in a 1990 trade and played well for them, including helping them win the AL East with a diving catch in the ninth inning of the season’s final game to save the victory and clinch the division. Between 1990 and 1992 “Bruno,” as he was called, hit .254 with 46 home runs and 144 RBI. After leaving in 1994, he came back in 1994 for the final season of his career and hit 10 home runs and 34 RBI in 48 games before the strike ended the season and his career.

Finally, we’ll end with a trio of players who began their Red Sox careers in the late 1990s but didn’t become Red Sox legends until they blossomed in the 2000s. Jason Varitek and Derek Lowe were acquired in the same trade in 1997 in one of the biggest heists in franchise history. The Red Sox swindled the Seattle Mariners by sending reliever Heathcliff Slocumb in return for the duo.

Varitek, of course, would go on to be the Red Sox catcher and captain until his retirement in 2011 and Lowe would be a valuable starter and reliever (including a 20-win season in 2002). Both were vital in helping the Red Sox win the World Series in 2004. Their teammate Trot Nixon was also crucial in ending the 86 year drought.

He came up with the Red Sox in 1996 and was a mainstay in right field through the 2006 season before finishing the final two seasons of his career elsewhere. All three of these players were core players of the 2004 champions but were just starting their careers in the late 1990s when the Red Sox made the postseason in 1998 and 1999.