New York Yankees legend Reggie Jackson spent a lot of time hitting home runs on the baseball diamond. Off it, he put together quite the collection of vintage cars. Jackson’s obsession with cars came long before his MLB playing days. It began when he was a kid, and it all started with a glass of Kool-Aid.

Mr. October is a baseball legend

Reggie Jackson was the second overall selection in the 1966 MLB draft, taken by the Kansas City Athletics. Jackson didn’t waste any time getting to the big leagues as he made his MLB debut in 1967 when he played 35 games for the A’s.

Jackson spent nine seasons in the Athletics organization and then had five very productive seasons with the New York Yankees after spending the 1976 season with the Baltimore Orioles. Jackson spent 21 years in Major League Baseball and was a 14-time MLB All-Star.

Known as Mr. October for his postseason heroics, Jackson was a member of five World Series championships. In 1973, Jackson won the Most Valuable Player Award and helped propel the Oakland Athletics to a World Series title. In that season, Jackson smacked 32 home runs, scored 99 runs, and drove in 117 runs, leading the league in all three categories. He also his .293.

For his career, Jackson finished with 563 home runs and drove in 1,702 runs. He had a career batting average of .262. He was inducted into the Hall of Fame in 1993.

Jackson’s love for vintage cars

Reggie Jackson‘s affinity for cars goes way back to his childhood days as he and his friends would sit outside and admire the cars as they drove by. Jackson and his buddies would play a little game as they watched the cars pass.

“We sat on the front porch in the summer, And six to eight kids … we would name the car. Say a Bel Air…or an Impala,” Jackson said in an interview in 2018. “And then, if you could catch an insignia on the side of a ’62 and see if it was a 327 (cubic-inch engine) or if it was a 409, you got points for that, too.  You got points, and you won a glass of Kool-Aid. That’s how I started out.”

“In the ’60s (my father) had a route, as I had a paper route, of about 70 or 80 people … so we ran around and picked up their clothes and dry cleaning and brought them back to them a couple days later,” Jackson said. “Sometimes you had to fix the truck or change the carburetor or a fan belt or something like that to keep them running. So we’d be out there busting our knuckles and scratching up our hands getting them running, so you just kind of got into the understanding of how the mechanics worked on a car. And that’s kind of how I got into cars.”

Jackson said the first car he bought was a ‘51 Chevrolet with leather bearings that he got from his brother for $5. At 15, he saved up his paper route money to buy a ‘51 Ford. “And then, when I was 16, I bought my dream car, which was a ‘55 Chevy,” he said.

Jackson parted ways with some cars

Reggie Jackson celebrated his three-home run game in the 1977 World Series by purchasing a Rolls Royce the next day and then driving it cross country. Now he’s in his 70s, and he’s doing more selling than buying.

In 1988, a fire destroyed 35 of Jackson’s vintage cars, damaging millions of dollars worth of his prized possessions. At the time, he had 97 vehicles, and the others were stored in another area. In 2018, Jackson decided to put up 19 of his antiques up for auction, saying, “There comes a time in life where you’re ready to let just about anything go except for family. I guess I have some cars that you could say are family.”

Jackson said he was going to hold on to some of his most prized possessions — at least for the time being. “I probably have a good half dozen I wouldn’t part ways with. I have a Ferrari that’s worth probably $15 million, and I’m going to sell that in a couple years. I’ve got some cars I love and like having around, but you know, they all come to a point where it’s time to let them go, and I think it’s time for me to pare my collection down.”