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Pinstripe Alley Top 100 Yankees: #36 Reggie Jackson

“Mr. October” only needed five seasons in the Bronx to become a legend, thanks in large part to his brilliant play in the postseason

New York Yankees Photo by Focus on Sport/Getty Images

Full Name: Reginald Martinez Jackson
Position: Outfielder
Born: May 18, 1946 (Abington, PA)
Yankee Years: 1977-81
Primary number: 44
Yankee statistics: 653 G, .281/.371/.526, 115 2B, 14 3B, 144 HR, 149 wRC+, 17.2 rWAR, 18.2 fWAR


Whether you want to call him “Mr. October” or “the straw that stirs the drink”, Reggie Jackson has a special place in Yankees history. He only played five seasons in the Bronx, but they included three pennants and two World Series championships. The talented, confident outfielder retired with 563 career home runs and was the definition of a winner during his playing days.

The Early Years

In baseball, and in professional sports, there are athletes whose hard work and discipline allow them to reach new heights and become stars. Others, like Jackson, are born to make history. This isn’t to say that Jackson’s journey didn’t include lots of hard work, but from a very early age, Reggie had the talent and the self-confidence to achieve great things.

Jackson was born on May 18, 1946, in Wyncote, Pennsylvania. He loved sports very early on, and that’s mainly because of the influence of his father, Martinez Jackson. He, according to Britannica, was the one encouraging young Reginald (yes, that is his birth name) to become an athlete at Cheltenham High School in Pennsylvania.

His family decided to go with an odd family arrangement when Reggie was a kid, according to his SABR (Society of American Baseball Research) bio: his father and his mother, Clara, split, with the former raising Reggie, his older brother James, and an older half-brother, Joe. She left with three of the children.

A Multi-Sport Star

There, at Cheltenham, Jackson was a very good football, basketball and baseball player, but he also excelled in track. He always drew attention from scouts because of his all-around natural ability.

That said, he wasn’t a stranger to adversity. He hurt his knee in an early season football game in his junior year in 1962 (he was a tailback) and was not supposed to play again according to doctors. He returned for the last game of the season, but in that contest, he fractured five cervical vertebrae. He was told his ability to walk could be compromised, but it’s safe to say he did much more than that and beat the odds in an impressive recovery.

Despite constant attention from scouts, Jackson’s father urged him to go to college and he did just that, at Arizona State University (Tempe). According to Matt Kelly of, he chose ASU because it was willing to let him be a two-sport athlete: he wanted to play both football and baseball.

After his freshman season there, he switched permanently to baseball. Suffice it to say, it was the right decision. Legendary head coach Bobby Winkles assigned him to a Baltimore Orioles-affiliated amateur team called Leone’s, and Jackson broke out.

By 1966, his sophomore year, Jackson had taken Rick Monday’s job as the team center fielder. He proceeded to break the record for most homers in a season on his team and pace his squad in other relevant statistical categories. He was a first-team All-American, and his future was bright.

Making His Way to the Big Leagues

After just a couple of years in college, Jackson was selected second overall in the 1966 MLB Draft by the Kansas City Athletics. The 20-year-old signed with the A’s for $85,000.

Jackson was assigned to the low Class A Northwest League, but made it to Modesto of the High-A California League relatively quickly. His short minor league career was completed with the company of some really promising names that, like him, would have an impact on the game: Rollie Fingers, Joe Rudi, and Dave Duncan.

They say even the greatest players get to know adversity and struggles at least once in their careers. For Jackson, that moment was 1967, when he was called up to the majors.

In 35 games and 135 plate appearances, Reggie hit only .178 with a 71 wRC+. He was sent back down, and per his SABR bio, he had problems handling it.

The demotion was difficult for him emotionally, but Birmingham manager John McNamara provided important support. McNamara managed Jackson again in Oakland and Anaheim, and Jackson said his help was essential for a 21-year-old trying to grow up and handle both success and failure in a Deep South environment

Jackson was able to shake of the disappointment. In 1968, his age-22 campaign, Jackson would take off. He hit .250/.316/.452 with 29 home runs, 74 RBI, 14 stolen bases and 4.7 fWAR, plus a much improved 137 wRC+.

Reggie would earn the first of his 14 All-Star berths in 1969, after belting 47 homers, driving in 118 runs, and posting a 179 wRC+ and 8.9 fWAR. With 40 of those bombs coming before the beginning of August, Jackson was so hot in the first half that he looked like he might approach Roger Maris’ record of 61. He was, just in his second full season, one of the best players in MLB.

Jackson would spend some of the best years of his career with the Athletics, who had relocated to Oakland in 1968. There, he won an AL MVP award in 1973, three World Series championships (1972-74), and a World Series MVP in 1973, wowing fans across the country with tape-measure homers along the way. Not too shabby.

Sports Contributor Archive 2020 Photo by SPX/Ron Vesely Photography via Getty Images

In April 1976, he was traded to the Baltimore Orioles amid a salary dispute with Oakland. Although this chapter has been mostly forgotten in his long history, he went on to play another excellent season there (27 home runs, 28 stolen bases, 156 wRC+, 4.8 fWAR) before signing a free agent deal to play for the New York Yankees ahead of the 1977 campaign.

A Golden Chapter: The New York Yankees

Now, the Yanks were surging again after a rough period. Since their World Series loss in 1964, they hadn’t made the playoffs until 1976, when they lost the Fall Classic against the Big Red Machine, the Cincinnati Reds, via a sweep.

The Yankees were determined to get back where they belonged: the top. So, they went out and signed Jackson to a five-year contract worth $2.96 million, a boatload of money at the time.

Manager Billy Martin wasn’t particularly keen on bringing in Jackson, though, which led to some well-documented issues between the two. Even with that being the case, that first season Jackson had with the Bombers, in 1977, was magical. He was 31 by that time, but boy, did he have something left in the tank. He slashed .286/.375/.550 with 32 round-trippers, 93 runs, 110 RBI, 17 steals, a 153 wRC+ and 4.9 fWAR. Those are some fine numbers, but we were about to see him at his best in the postseason.

The Yankees defeated the Kansas City Royals and made it back to the World Series. Martin chose not to start Jackson in the decisive Game 5, but he came off the bench to deliver a key RBI hit in the eighth. Then in the ninth, New York plated three to take the series.

The Fall Classic brought forth the most memorable performance of Jackson’s career. In large part thanks to him, they would avenge their 1976 loss to the Cincinnati Reds by taking out the Los Angeles Dodgers in six.

“Mr. October”

With the Yankees leading the series 3-2, in Game 6, he would hit not one, nor two homers. He would go yard three times to make sure New York celebrated that night. He did it on just three pitches, against three different hurlers. “I felt like Superman,” he said, and you bet he did. He was, from that point on, “Mr. October”.

Reggie’s self-confidence is the stuff of legends. As the National Baseball Hall of Fame wrote it, “in 1973, as a member of the Oakland Athletics, Jackson said that if he was playing in New York, they would name a candy bar after him. Within five years, those words came true.” He also became famous for his phrase “I’m the straw that stirs the drink,” and you know what? He was.

With five home runs in six games, he took home World Series MVP honors for the second time in his career. He hit .450/.542/1.250 with a 1.792 OPS in that Fall Classic, cementing his status as a “money” player.

Jackson would win his fifth World Series as a player in 1978. His clashes with Martin and owner George Steinbrenner would lead to a messy divorce, as Martin resigned as Yankees skipper midseason after lambasting both of them. Bob Lemon took over, the Yankees pulled off a stunning rally to overtake Boston (with Jackson homering late in Game 163 after Bucky Dent), and they came away with a championship. Before that, he would have his typically excellent regular season: .274/.356/.477 with 27 dingers, 97 RBI and a 138 wRC+.

In the Fall Classic rematch against the Dodgers, Jackson would hit .391/.500/.696 with two homers, eight RBI, and a 1.196 OPS. Bucky Dent would take home MVP honors this time, but “Mr. October” still churned out a memorable moment when he took vengeance on young Bob Welch for striking him out to end Game 2 by going yard off the rookie in Game 6.

Jackson would stay three more seasons with the Yankees. They failed to make the playoffs in 1979, but returned to the big party in 1980. An ALCS exit put a sour end to a phenomenal year by Jackson, who hit .300 with a league-leading 41 home runs, plus 111 RBI and a 169 wRC+. He thrived under skipper Dick Howser and finished runner-up to George Brett for the AL MVP.

With fellow superstar Dave Winfield in tow for 1981, New York made it back to the World Series, this time losing to Ron Cey, Steve Yeager, Fernando Valenzuela and the Dodgers. An injury suffered while running the bases in the ALCS forced Reggie to miss the first three games of the Fall Classic, but he came back to have a 1.095 OPS in the remaining three. Those turned out to be the final Fall Classic at-bats of his career — and his last in pinstripes.

Leaving New York

Steinbrenner made a decision that he would personally say that he regretted during the 1981-82 offseason by letting Jackson walk. The 35-year-old veteran signed a five-year deal with the California Angels. With him, they made the ALCS in 1982 and 1986, and Jackson belted his 500th his career homer. At the time, he was one of just 13 players to reach that milestone.

After enduring heartbreak in the 1986 ALCS, Jackson departed the Halos for one last rodeo in Oakland for 1987. Although it was only a .500 team, he got to play with Mark McGwire and Jose Canseco, who would soon lead the A’s to their late-’80s American League dominance. Jackson belted 15 more long balls and called it a career. He made the National Baseball Hall of Fame on the first ballot in 1993.

For his career, Jackson’s numbers were truly fantastic. Yes, he had a tendency to strike out (a record 2,597), but he more than made up for that with 563 home runs, 1,702 RBI, 228 stolen bases, a .262/.356/.490 line, a 139 wRC+, and 72.7 fWAR. He also retired with 2,584 hits.

Jackson’s list of accolades is long and impressive: 14 All-Star Games, five World Series championships, two World Series MVPs, the 1973 AL MVP award, two Silver Slugger awards, and four home run crowns in the American League. He has a plaque in Monument Park and is a member of the Athletics’ Hall of Fame, having his number retired in both franchises: 9 with the A’s, and 44 with the Yankees.

Perhaps more importantly, Reggie was at his best when the lights were brightest. He retired with a cool .278/.358/.527 line and a .885 OPS in postseason play, including 18 home runs.

Post-Playing Career

Martinez Jackson got to enjoy his son’s HOF induction ceremony, but died the following year. Reggie did keep in contact with his mother and siblings despite not growing up together.

Jackson, who has a daughter named Kimberly, was for many years a senior advisor for the Yankees before departing due to disagreements with the front office. He had his ventures in the artistic world, working on TV shows such as The Love Boat, Diff’rent Strokes, MacGyver; and also some movies, like Ri¢hie Ri¢h, BASEketball, Summer of Sam, and, most famously, The Naked Gun: From the Files of Police Squad!

Since 2021, Reggie has been working for the Houston Astros as a special advisor to owner Jim Crane, focusing on community support and leading some really interesting projects.

Jackson has lived a colorful life, and the Yankees are a big part of it. He “only” played in the Bronx for five seasons, but he made them count. He was a star during his playing days and has been a revered figure (and the gold standard for postseason production and heroics) after his career. Those five years were more than enough to make him a franchise legend.

Chicago White Sox v New York Yankees

Staff rank: 33
Community rank: 20
Stats rank: 76
2013 rank: 62



Baseball Reference


Leavengood, Ted. SABR Bio

National Baseball Hall of Fame

Perry, Dayn. Reggie Jackson: The Life and Thunderous Career of Baseball’s Mr. October. New York: itBooks/HarperCollins, 2010.

Sporting News

Previously on the Top 100

37. Tommy Henrich
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