OTM Roundtable: Most underappreciated non-champ

It’s underrated/underappreciated week here at OTM, and we’ve spent the week going through some of the most underrated players from all four of the championship teams from this past century. For this week’s roundtable, we’re going to look at the players who didn’t win.

Jake Kostik

Somehow, someway, it’s yet again Adrián Beltré.

He only played in Boston one year, and he was basically an all-star player. An all-star player we should have never let walk out that door. An all-star player that never won a World Series anywhere, not just in Boston. Despite being an all-star player, though, there are still people who seem to have forgotten just how good of a player he was with the Red Sox. Here is a list of the best players from 2010. You’ll note that Beltré ranked 9th in fWAR. And he could have been even better if he walked at all.

He was a top level player on both sides of the ball, and also a top level character on the field.

I really wish we’d kept him beyond 2010. Over the next five years in Texas, he would hit .309/.358/.514, and average 27 HR and 3,a3 doubles per season. He accrued 26.9 fWAR over those five years (2nd most in baseball over this time frame), while Red Sox third basemen totaled 8.6, which was in the bottom 10 teams in baseball over this time frame. Had Beltré stuck around, he would have had a chance in 2011, as well as probably been around when we won it all in 2013.

Michael Walsh

One of the most underappreciated Red Sox players who never won a World Series is former left fielder Mike Greenwell. Nicknamed ‘Gator’, Greenwell is underappreciated mostly thanks to the left fielders that came before him. He faced the tall task of carrying on the left field legacy of Ted Williams, Carl Yastrzemski, and Jim Rice. While Greenwell was never as effective as the aforementioned Hall of Famers, he batted .303 with an OPS+ of 121 for his career, and played all 12 of his seasons with the Sox. A two-time All-Star, Greenwell finished second in MVP voting in 1988, losing to Jose Canseco. However, he outperformed Canseco in batting average, OBP, and bWAR, and was arguably robbed of an MVP award due to old-school thinking. Perhaps in a different era, without the shadows of Ted, Yaz, and Rice, Greenwell would be remembered differently.

Phil Neuffer

John Valentin missed the vindication of the 2004 World Series title by just a few years. He was there all through most of the build up in the 1990s and early 2000s, but he left Boston after the 2001 season and retired after spending one year with the New York Mets. Valentin had a lot of legendary Red Sox teammates, including Nomar Garciaparra, Pedro Martinez, Mo Vaughn and Roger Clemens, but he isn’t thought of in that realm despite being an excellent infielder for a seven-year stretch between 1992 and 1998. During that run he slashed .287/.369/.472 and produced a 116 OPS+. He was worth at least four bWAR in five of those seven seasons, including his signature 1995 campaign when he set career-highs in home runs (27), stolen bases (20), walks (81), OPS (.931) and OPS+ (138) en route to a personal-best 8.3 bWAR campaign.

Valentin was just a bit ahead of his time at the plate, as the Moneyball-powered obsession with on-base percentage wouldn’t take place until after he retired. However, he was an exceptionally patient hitter who consistently made contact. He never struck out 100 times in a season and he had more walks than strikeouts in multiple seasons.

In addition to his walking prowess, Valentin was a doubles artist. While the rest of MLB was falling in love with the home run more than ever, he smashed 281 in his 11-year career, including an AL-leading 47 in 1997. That was one of his three seasons with at least 40.

Despite all that statistical success, Valentin never got the recognition he deserved. He did win a Silver Slugger and finish ninth in AL MVP voting in 1995, but he was never considered for either award at any other time and he never made an All-Star team, which is a shame. He also never won a World Series and that’s a shame as well.

Shelly Verougstraete

I’m going to go with John Valentin here. He played on the team from 1992 to 2001 and hit .281/.361/.460 for a 110 OPS+. In 1994, he turned an unassisted triple play, the tenth one in MLB history, when he caught a line drive, tagged second base, and then tagged out a runner attempting to go to second. Valentin played shortstop for most of his career before someone named Nomar came along when he shifted over to second base. His best season was in 1995, when he finished ninth in MVP voting and hit .298/.399/.533 for a 138 OPS+. His production died off towards the end of his time with the Sox but John Valentin deserves a bit more love.

Mike Carlucci

With the challenge this week posed as “Underappreciated” and “did not win a World Series” I’m going assume Ted Williams (definitely not underappreciated) and Nomar Garciparra (received a ring but wasn’t actually on the 2004 team when they won) are ineligible for this particular honor. While I’m sure there are many players who meet this definition from before I was born, given the 86 year championship drought, I’m going to go with a player who was ahead of his time and left the game a shadow of himself: Mo Vaughn.

Vaughn’s run in Boston lasted 8 years and saw him hit .304/.394/.542 with 230 of his 328 career home runs. He won an MVP award in 1995, represented Boston in three All Star Games, and was worth 24.7 WAR. He led the league in strikeouts during his MVP year with a quaint 150 - which would have been 26th in 2019. Truly a different era. Vaughn had two playoff runs in his career in 1995 and 1998 - both against Cleveland. And while in the ‘95 ALDS Vaughn did hardly anything, his 1998 self hit a pair of home runs and slugged nearly .900 in the four-game defeat. But that was it for his postseason play.

Bryan Joiner

I’m probably getting over my skis here, but is Dom DiMaggio the most underappreciated player who did not win a World Series? I’m far too young to have seen him play but the exact right age to have heard the people who did see him play that if he had any other name, he’d be in the Hall of Fame. You could probably add that if the Sox had actually won the World Series with him, he’d have a shot, though his numbers aren’t all that great... but then again, he missed his age 26-28 seasons, his absolute prime, for the war. If he’s remembered now it’s as a trivia answer, but he was not trivial.

Jake Devereaux

In April of 1995 Troy O’Leary was claimed off waiver by the Red Sox after spending the first part of his career with the Brewers. He had previously gotten light playing time, but the Red Sox immediately thrust him into the lineup. Manning left field at the time was Mike Greenwell who had taken over left from Rice when he had retired and Rice had taken it over from Yaz. If you haven’t heard me gush about left field at Fenway then you haven’t been listening. Troy honed his skills as Boston’s primary right fielder before switching to left full time in 1998. For the next three season’s he’d be the primary left fielder for the team and he put it all together in 1999. At 29 years old and batting fifth in the lineup O’Leary thrived posting a line of .280/.343/.495 with 28 home runs and 103 RBI all while playing fantastic defense.

His big moment came in the decisive game five of the 1999 ALDS vs the Indians. This game was played on the road and O’Leary himself was responsible for the game’s two biggest moments. In the top of the third inning with the bases loaded and the score 3-5 in favor of the Indians O’Leary crushed a grand slam to put the team up 7-5. The Indians had an incredible offense and battled back to take the lead. After battling back to an 8-8 tie O’Leary came up in the top of the 7th and blasted a three run shot to put the Red Sox up 11-8 sealing the victory for the good guys. O’Leary was a good player not a great one, but he came up huge in big moments. I always loved watching him and I would’ve loved to see him get a ring with the team.

Keaton DeRocher

Jason Bay was only with the Red Sox for a short time but while he was here he was very productive. Acquired mid-year 2008, he finished the season slashing .293/.370/.527 and stepped it up in the playoffs slashing .341/.471/.634 across 11 games. The following season he lead the Red Sox in homers, runs, and RBI and was the only player on the roster to eclipse 100 runs and RBI. The 2009 postseason was a downer getting swept out of the ALDS versus the Angels but again Bay was productive getting on base more than any other player on the roster. The best baseball of his career was played in a small window with the Red Sox and I don’t think he gets enough credit for being a major reason that 2009 team even made it to the playoffs in the first place.

Matt Collins

I’m going to go back a bit and talk about a player who I did not see, so I cannot say with any sort of certainty that he was underppreciated in his time. I do think we don’t talk enough now, however, about how good Reggie Smith was. Playing next to Carl Yastrzemski and Dwight Evans in the outfield certainly didn’t help matters, nor did shortly after leaving being succeeded by Fred Lynn.

Smith was a monster for the Red Sox in the late 60s and early 70s, though. He was a consistently four-to-five win player year after year who drew walks, made contact and hit for power. He was never the best player on the team, but he was always one of the top three or four. It doesn’t help that he only made it to the postseason once with the Red Sox on that 1967 team, and that was his rookie year when he was good but still just settling into his role. He’d end up winning a World Series later in his career with the Dodgers — in his fourth appearance in the Series — but he never won one with the Red Sox. Maybe he’d get more respect if he did, because despite playing just eight years of his career here, he is 21st on the all-time Baseball-Reference WAR leaderboard in franchise history.