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Pinstripe Alley Top 100 Yankees: #40 Rickey Henderson

The Hall of Famer’s tenure in New York only lasted so long, but he was an absolute supernova during the ‘80s.

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1985 Major League Baseball All-Star Game

Name: Rickey Nelson Henley Henderson
Position: Left fielder
Born: December 25, 1958
Yankee years: 1985-89
Primary numbers: 24
Yankee statistics: 596 G, 2,735 PA, 663 H, 78 HR, 326 SB, .288/.395/.455, 135 OPS+. 30.8 rWAR, 29.7 fWAR

Biography

Rickey Nelson Henley Henderson is the greatest base stealer of all time, and one of the 10 best outfielders to ever the play the game. His legacy on the game of baseball is historic. He is the only player to ever surpass 1,000 stolen bases and has over 400 more than the next player, Lou Brock. There are some records in baseball that will never be broken — his stolen base mark is perhaps the most untouchable.

Playing in four different decades and nine clubs, his Yankees’ tenure spanned from 1985-89. Unlike his 100-WAR peers, he donned many different jerseys, although the green and yellow was most prominent. Even with that, some of his best years came in pinstripes, but he was always destined to return to his hometown Athletics. Rickey was born in Chicago but hopped around a few when he was young, as his mother, Bobbie, sought out opportunities for her family with minimal support from his father. Henderson ended up in Oakland after temporarily living in Arkansas, and the rest is history.

San Francisco Giants v Oakland Athletics Photo by Michael Zagaris/Oakland Athletics/Getty Images

Childhood

Rickey grew up in a big family with four brothers and two sisters. He was a superstar athlete in Oakland from a young age. He was a three-sport athlete, excelling in baseball, basketball, and football. He was well known around the city as the next big thing. His speed was uncanny for a high school athlete and a big reason for his football dominance. Henderson’s dream was to play pro football, but his skills in baseball complicated that. He had a choice when he finished up high school: college football scholarship or straight to professional baseball. That choice was left to his mother. She was aware of his dreams, but thought baseball was the better option. She was correct.

Rickey was drafted by Oakland a few months later in the fourth round. He was excellent throughout his minor league career. Specifically, his 1977 season was the one that would foreshadow his future profile, most importantly his stolen base success as he swiped 95 bags during that season. His relationship and skill development with his manager, Tom Trebelhorn, was a key reason why Rickey felt so confident with extreme aggression on the basepaths.

Trebelhorn helped Rickey pick up on the fine details of stealing bases by studying Lou Brock and watching video of pitcher tendencies. This advanced scouting work was crucial for Rickey to understand the important aspects of base stealing that don’t take just natural speed. After this, his base stealing success reached the level we know of today.

Toronto Blue Jays v Oakland Athletics

The Beginning

Rickey’s rookie campaign was nearly two-thirds of a full season. It did not go as planned. Across 89 games, he was below replacement level, his defense was subpar, and his offense was just below average despite his 33 stolen bases in limited time. His mere one home run came as a surprise, given that he showed decent power in the previous two minor league seasons. On the surface however, Henderson’s performance was probably interpreted as decent given the time period. He had a .274 average and still swiped bags as expected. Other than power, it’s reasonable to squint and say it was a solid rookie year. The team had fewer than 60 wins, so it was good to see at least one player with promise.

In 1980, Henderson splashed onto the scene with an enormous cannonball. His sophomore line was one of the best five seasons in his career. Here are some of the notable stats from that year: 7.8 fWAR, 8.8 rWAR, 136 wRC+, 100 stolen bases, .303/.420/.399 slash, 16.2 percent walk rate, 7.5 percent strikeout rate. Now that is incredible.

In terms of total value, Henderson had a strong case for an AL MVP, but his team stunk and George Brett nearly hit .400 while delivering a nine-win season for the pennant-winning Royals. Rickey ended up finishing way too low on the ballot at 10th overall, receiving less than 15 percent of the voting share. Either way, it was clear from this season that Henderson was a superstar with one of the most exhilarating tools in baseball.

If not for missing nearly a third of the season in 1981 due to the strike, Henderson would have likely put together a 10-win season. His follow-up to his sophomore campaign was even better on a rate basis. His 152 wRC+ and power tick up fueled his 6.7 fWAR in just over 100 games. He finished second in the MVP voting behind none other than … closer Rollie Fingers! Huh? Fingers’ season was fantastic with a 1.04 ERA in 78 innings, but Rickey was amidst one of the best seasons in baseball history! It was a different time. Unfortunately, it wasn’t the first time the voters did him dirty.

Over the next two seasons, Rickey wasn’t quite as productive in terms of overall value, but was still excellent. His offensive numbers were not quite as compelling, but his stolen base king reputation began to build. In 1982, he swiped 130 bags and in 1983, he swiped 108. This was the only time in his career where he took triple-digit bags in consecutive seasons. If not for the strike in 1981, he would’ve had a shot at four in a row.

His mark of 130 thefts in ’82 broke Lou Brock’s record, officially stamping Henderson as the single-season king at just 23 years old. This season was historic for Rickey despite not being his best in total value. He also led the league in walks with 116. Pitchers made a big mistake in allowing him to get on first so often, but the team’s offense had no slugging, so leaving even somebody like Rickey on base didn’t pose much of big inning threat.

Welcome to the Bronx

After the 1984 season, Rickey was on the trading block. The Yankees were coming off an 87-win, third-place performance. Don Mattingly, Willie Randolph, and Dave Winfield were at their peaks. The team was in win-now mode and a big splash could help elevate them. Right before Christmas, they acquired Henderson for five players. That package included the likes of future All-Star José Rijo and longtime outfielder Stan Javier, but you make that trade to get an otherworldly talent like Prime Rickey every single time.

Henderson promptly signed a five-year, $8.6 million deal to stay in the Bronx for a half-decade. The acquisition would prove to be a fantastic decision by general manager Clyde King.

In 1985, the Yankees finished with 97 wins, but that was only good enough for second place. Toronto was on a run of excellence and churned out 99 victories to eke out the AL East crown. Regardless, the campaign was more successful than the last. A key reason for that was Rickey’s incredible splash of a season. With 9.7 (!) fWAR and a 156 wRC+, Rickey put on a show in the Bronx. He stole 80 bases while playing incredible defense for the team as well. It was the first 20-homer season of his career, and his power really came onto the scene with the team for the next three years.

Despite his legendary year, Rickey’s success was probably the main reason why his teammate, Don Mattingly, won the MVP award instead. His slash line of .324/.371/.567 was nearly a deadlock with Rickey in terms of OPS (.939, .934), but because the Hall of Famer was on base so often in front of him (.419 OBP), Donnie Baseball set a league-leading mark of 145 runs batted in. This meant a lot to voters then, but they got this one wrong. That’s no disrespect to Donnie Baseball’s outstanding year; Rickey had simply posted one of the most productive seasons seen by a Yankees player since the days of Ruth and Mantle.

At age 27, Henderson continued in his superstardom but under a new manager in Lou Piniella. The former outfielder was respected for the intensity and intelligence he brought to the club, but his relationship with Rickey paled in comparison to the one forged with skipper Billy Martin, who was close with Henderson in Oakland (a bond that would continue whenever his path brought him back to the Bronx). Even so, he kept up his superstar performances with another six-win season.

If not for straining his hamstring and missing almost half the year in 1987, Rickey likely would have made another run at MVP and put more confidence in his manager. Unfortunately for him, the Yankees took a bit of a fall under Piniella and Rickey was used as a scapegoat despite being one of the best two players on the team. In 1988, Piniella was let go while Rickey delivered another five-win season, setting a Yankees franchise record with 93 steals.

However, in the following year, Rickey’s performance at the plate took a significant drop off while the team’s did as well. With New York going nowhere, they decided to surrender the superstar. Rickey was traded midway through the year back to his hometown Athletics, where he quickly took off again.

If not for the team’s lack of championship success during the ‘80s, Rickey would have likely stuck around in New York and gone down as one of the best players in franchise history. His 29.7 fWAR during his tenure is among one of the best stretches for a player while in pinstripes. He is second in franchise history in stolen bases (326) behind only Derek Jeter (358), who played over 2,000 games more. Henderson is 11th in OBP and 14th in wRC+.

Rickey has the numbers of one of the best players in franchise history; sadly, like other players from this era of Yankees baseball, he had no rings then to show for it. The absence of the Wild Card hurt them, but they should still have won a division. Although the man was a supernova on the field, baseball is a sport that only does so much to allow a few stars to carry whole teams to playoff glory (ask Mike Trout and Shohei Ohtani). There are five other players who have had at least 9.5 fWAR in a single season while flexing the pinstripes. You may be familiar with them: Babe Ruth, Lou Gehrig, Aaron Judge, Mickey Mantle, and Joe DiMaggio. And Rickey was hardly a one-year wonder.

Rickey Henderson doesn’t fit in with the rest in terms of Yankees’ lore, but his 1985 campaign was just as historic. This type of season makes you appreciate just how transcendent he was during his limited time in the Bronx. There’s an alternate universe where the team is more complete, they go on a playoff run or two in the ‘80s to add to the trophy collection, he stays in New York, and he wears a Yankees cap in Cooperstown. Alas.

New York Yankees

Jumping Around the League

After being traded back to Oakland, Henderson won it all in 1989 and then had the best season of his career in 1990 when he hit to the tune of a 190 wRC+ and 10.2 fWAR. Rickey was a monster alongside the Bash Brothers — in fact, he was the real show, with an OPS over 1.000 and 65 stolen bases. After several seasons more than deserving of being crowned the league’s best player, Rickey finally capture the AL MVP. It took the man putting up a 190 wRC+ to finally win the award, but there is no question some of his previous seasons were more than deserving.

In today’s game, Rickey would likely be heralded as the best position player in the game, but in his era, that was not the case. Mattingly was well regarded as the team’s best player when they shared the spotlight, and his overall drop in performance in the years following his mid-’80s peak gave opportunity to other players to take the spotlight.

Los Angeles Dodgers v New York Mets

Henderson was traded to the Blue Jays down the stretch in 1993 and won a second World Series after sparking a rally in the ninth inning of the victorious Game 6 (capped by Joe Carter’s unforgettable bomb). Although Rickey’s power numbers permanently fell off in 1994, he still continued to hit at an above average rate, peaking at a 135 wRC+ in 1999 with the Mets at the ripe age of 40! After that, he bounced around from Seattle to San Diego, to Boston, and then to LA with the Dodgers following a stint with the Indy ball Newark Bears.

Perhaps Rickey could have retired a few years earlier, but he was still a solid player other than his final season. When it was all said and done (and he did still play minor league ball for a few more years), he accumulated over 100 WAR and cemented his spot as one of the best players in league history. He was inducted into the National Baseball Hall of Fame on the first ballot in 2009. Until this year, Henderson’s skillset had looked extinct, but thanks to the many power-speed players of 2023, it seems as if we may get the chance to see it again, but none will ever be to the extent of Rickey.

Staff Rank: 40
Community Rank: 49
Stats Rank: 38
2013 Rank: 38

References

Baseball Almanac

Baseball Reference

Bryant, Howard. Rickey: The Life and Legend of an American Original. Mariner Books: Boston, 2002.

The Dollop

FanGraphs

Ghiroli, Brittany. “Rickey Henderson on MLB’s new rules: ‘You gotta let these kids run.’” The Athletic, 27 Mar 2023.

National Baseball Hall of Fame

Upper Decker

Wancho, Joseph. SABR Bio

1990 AL MVP Voting

Previously on the Top 100

41. Bobby Murcer
Full list to date