This is Shakeia Taylor’s second piece as part of her April Residency at FanGraphs. Shakeia is an avid baseball fan and baseball history enthusiast. Her main interests include the Negro Leagues and women in baseball. She has written for The Hardball Times and Complex. She hosts an annual charity bartending fundraiser for Jackie Robinson Day, all of tips and raffle proceeds of which are donated to the Jackie Robinson Foundation. Though not from Baltimore, she’s still an Elite Giant. Shakeia can also be found on Twitter (@curlyfro). She’ll be contributing here this month.

Given the racial makeup of Major League Baseball, it might seem like baseball’s culture would be largely distinct from hip hop’s, but it isn’t really. Many players warm up to hip-hop music and use its songs as their walk-ups. In 1993, Seattle Mariners superstar Ken Griffey Jr. chose Naughty By Nature’s “Hip Hop Hooray” as his walk-up song. The song would eventually become his personal anthem. Roc Nation, Jay Z’s entertainment company, represents baseball players, including Robinson Cano and Yoenis Cespedes.

And the game’s influence has been felt in hip hop, as well. Baseball caps, also known as fitteds, have become a mainstay in hip-hop culture. In a game that can at times feel dominated by pop country music, hip hop’s prominence in baseball — and baseball’s presence in hip hop — offers a foothold for fans of both who wish to see their interests intersect.

The relationship between baseball and hip hop is particularly deep in Chicago. Jay-Z has his Yankees cap, but 90s rap videos were all about the White Sox fitted. It became a symbol of the culture at a time when rap was going mainstream and rappers from both coasts were gaining popularity. The design and color scheme of the cap are simple, yet timeless.

The most ubiquitous White Sox cap design — which is also the club’s current cap design — is actually drawn from the 1948 White Sox logo, and was designed by the grandson of White Sox founding owner Charles Comiskey, Chuck.

Chuck Comiskey borrowed the design from the 1948 Yankees uniform. That uniform, which isn’t much different from the one worn today, featured dark pinstripes on white jerseys and a dark blue hat, with a white, N-Y written in Old English style font. Over the course of three years, Comiskey’s new design evolved to include black pinstripes on off-white jerseys and a diagonal S-O-X on the chest. The Southsiders saw success in that uniform for a number of years, but after a dismal 1975 season, then-owner Bill Veeck decided to abandon the Old English S-O-X logo.

In 1989, Rob Gallas was hired as the senior vice president of the Jerry Reinsdorf owned White Sox organization. After getting a feel for the team’s shifting fanbase, he decided to bring back the diagonal Old English lettering.

For many years, the White Sox were associated with the white ethnic working class neighborhoods in the area surrounding Bridgeport, Comiskey’s neighborhood. In the period during which Gallas took on the task of revamping the uniforms, Chicago’s South Side had become increasingly African-American and Latino. After talking to some designers, Gallas learned that “silver and black were going to be the hot colors of the 1990s.” The new Sox logo and color scheme mirrored the high-selling merchandise of the Los Angeles Raiders.

Sports apparel was traditionally worn by fans, but the White Sox cap became a huge part of the urban lifestyle associated with rappers of the day. In 1991, Dr. Dre, Eazy-E, and Ice Cube, members of the rap group N.W.A., wore White Sox hats, officially marking a cultural shift and cultivating newfound significance for the White Sox cap among N.W.A.’s audience. At the time of the iconic rap group’s success, one could be hurt or even killed for wearing the “wrong” colors. The Sox cap, with its monochromatic color scheme free from association with a particular gang, gave the group and its fan a neutral option. The color scheme and clean feel made it easily adoptable among those who might not have even considered themselves baseball fans.

N.W.A. alum Dr. Dre wearing the iconic White Sox cap as a solo artist.

In July 2017, while Ice Cube was visiting Chicago with his basketball league, BIG3, former Chicago Bulls star Kendall Gill asked him why N.W.A. chose the White Sox cap. He replied, “Chicago changed their colors to black and white. It was perfect for us.”

With the popularity of N.W.A, White Sox gear flew off the shelves. At the end of 1990, the White Sox were 18th in product sales out of the then 26 teams in baseball. By August of 1991, they were third, behind the New York Yankees and Oakland A’s.

The hat is so closely tied to N.W.A. and the group’s success, that when a Sox cap was used in a scene in the 2015 movie Straight Outta Compton, which is set in the late 1980s, fans everywhere pointed out that the hat wasn’t worn by members that year because it hadn’t even been created yet. The team seems to have embraced that connection fully. In response to the wardrobe blunder, the Chicago Tribune reported that Scott Reifert, the club’s senior vice president of communications, said via email:

“When the White Sox introduced our new logo and color scheme, the popular black and white look immediately enjoyed cross-cultural appeal. As such, it has long been popular among all of our fans, including the hip-hop community that stretches back to the early days of NWA, Dr. Dre, Ice Cube and Eazy-E. That trend continues today with young artists like Chance the Rapper and Kendrick Lamar. Without having seen the movie, we can’t speak to the specifics. However, the White Sox black cap and logo, as seen in the movie trailer, was introduced in September 1990 by the organization and anecdotally, we understand that the White Sox logo was part of the group’s look throughout their successful music careers.”

In April 2016, the White Sox crossed into hip-hop culture again, this time with local rapper and hero, Chance the Rapper. Chance, a well-known fan of the team who is frequently seen wearing a Sox cap, was given the opportunity to design special edition White Sox caps with New Era. The hats were a huge success, selling out almost immediately. A new generation of Sox cap wearer was born. Chance also narrated the team’s hype video that season, proving once again, that baseball and hip hop culture can be a perfect match.

I partnered with New Era to redesign the White Sox cap. https://t.co/m5rYnxicio pic.twitter.com/C3zrYpExea — Chance The Rapper (@chancetherapper) April 6, 2016

Chuck D, Nas, Lil Wayne, Freddie Gibbs, Twista, and Common have all been spotted wearing the Sox cap. Kendrick Lamar, whose parents are from Chicago, wore it on the cover of Rolling Stone. Almost without meaning to, these two distinct bits of American culture have found themselves to be interwoven. The White Sox cap and hip hop have formed something of a virtuous circle, feeding off and reinforcing one another. And the team’s embrace of their cap’s legacy in hip hop has allowed them to connect with a new generation of fan, furthering their place in the genre. It has deepened the White Sox’ connection to a community that isn’t always well represented on the field, all while they wear the black and silver in their neighborhoods.