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Mr. October. Reggie Jackson was a legend. He was drafted second overall by the Kansas City Athletics in 1966 (first was catcher Steven Chilcott, an all-time bust for the Mets). Jackson debuted as a 21-year-old the following year and struggled, but from 1968 to 1975, he averaged:

True star numbers. He was an integral part of Oakland’s dynasty in the 70’s, helping the Athletics win three straight World Series titles.

Reggie was swagger—he referred to himself as the straw that stirs the drink. Darold Knowles, a teammate of Reggie’s on the Oakland A’s, said, “There isn’t enough mustard in the whole world to cover Reggie Jackson.” Looking at how the game has evolved, you could argue Jackson was ahead of his time.

Then in December 1975, pitchers Andy Messersmith and Dave McNally—having played a season without signing contracts—were ruled free agents by an arbitrator, paving the way for the first free-agent class after the 1976 season, helping shape the free-agent landscape we know today. A’s owner Charlie O. Finley refused to pay up, trading the Oakland legend to Baltimore for Don Baylor, Paul Mitchell, and Mike Torrez, a week before opening day. Reg threatened to sit out the season, but ultimately reported on May 2nd. After being booed in his first at-bat, he responded with a single in his next:

Though missing the playoffs for the first time in five seasons, he produced a classic Reggie season nonetheless: .277/.351/.502, with 27 home runs and a career-high 28 stolen bases.

After the season, Orioles legend Jim Palmer said, “I would say Reggie Jackson was arrogant. But the word arrogant isn’t arrogant enough”. Palmer later stated that the team made a huge mistake by letting him walk after the season in free agency. Jackson would sign a five-year pact with the Yankees for roughly $3 million, where he would go on to win two more rings, homering on three consecutive pitches in Game 6 of the ‘77 World Series, cementing his status as “Mr. October”.

Some saw Jackson as just passing through Baltimore. He denied that, however, saying,

“I wanted to stay. I liked the team. I liked the city. My mom was there. My dad was close by. I had other family close by. And I loved playing for Earl (Weaver). When I got there, he told me, ‘You know I like guys who can hit the ball over the fence, Reggie.’ And I said to him, ‘Earl, I can do that.’”

Reggie Jackson

Though his time was brief in Birdland, it’s remembered as one of baseball’s first true free-agent rentals—something we’ve all grown accustomed to today. Seeing Reggie in Orioles orange? Not so much.