Office Hours with Ernest Wilkins
Office Hours with Ernest Wilkins
#166: Brands to Watch 2021: The Chicago White Sox

#166: Brands to Watch 2021: The Chicago White Sox


If this is your first newsletter — welcome, by the way! — this podcast is the start of the 2021 Brands to Watch Spotlight, which kicked off in last Tuesday’s newsletter. For full context, you can read that by clicking this cute lil’ button.

Read Brands to Watch 2021

“Before this, I thought MLB stood for Major League Boring”.

When it comes to culture, actor/musician/activist/Chicago native LaRoyce Hawkins isn’t one to sugarcoat things.

He’s referring to his partnership with the Chicago White Sox, the team he grew up rooting for. Last season, the team reached out to him to talk about a new campaign they were working on. That campaign is just one of many calculated risks one of the most prestigious franchises in sports has undertaken over the last 5 years to build a bridge from the past to the present to the future.

In short, they wanted to Change the Game.

Bringing in folks like Hawkins seems like a no-brainer to most, but baseball isn’t exactly known for modern thinking. How do you combat declining popularity and claims of the game suffering from a lack of investment into diversity and inclusion?

If you’re the White Sox, you change the game AND what a team “looks” like.

The White Sox’s 35th and Shields streetwear-inspired collection

I mean, look at this stuff!

Let’s look at the breakdown:

So, why are the Sox such a Brand to Watch? Teams do cool t-shirts and campaigns all the time, right?

Here’s the difference: With a strong focus on serving the diverse audience that makes up their fanbase, I’m calling my shot now: By leveraging their cultural influence and putting together a solid on-diamond performance, the Chicago White Sox will overtake the Chicago Cubs to become the #1 team in Chicago in the future for the kids. I'm of the opinion that last season was the beginning of a cultural shift in how Chicago views the team, and that shift will culminate in a few things this decade, a few of which are already starting to happen:

1. More kids are going to start becoming White Sox fans.

2. The work that the team has done over the last few seasons to partner with creatives will pay off with renewed support and a bigger fanbase nationally.

3. The Sox will be looked at nationally as one of, if not the, coolest team in baseball, if not sports overall.

This is a cool hypothesis and all, but I needed to get to the bottom of the matter. Enter Gareth Breunlin, a forever-creative who worked his way up from an entry-level design gig with the team to become the Senior Director of Marketing & Advertising for the White Sox.

This might be the first time you get this kind of conversation with someone in the front office of a major sports franchise. More than business, the conversation is about how Gareth not only keeps up with culture — Spoiler Alert: He doesn’t expect the young people in the building to do it for him, hint hint, wink wink! — but has leveraged his creative background to take an innovative approach to marketing the team not only to Chicago, but the larger country.

I ain’t gonna hold you, this is a dream come true for a third-generation Sox fan like myself. If you work in a cultural industry that’s slow to innovation (aka most of them?) then this is a great conversation about how to change things from the inside.

Sidebar: Talking on-diamond, I wrote last year for Chicago Magazine about how the White Sox were going to become a team to watch. I’m doubling down on that for this year. Get on the bandwagon now, because I think it won’t be too long here before there’s another trophy on the South Side.


So far, season 2 has featured interviews with some big thinkers across cultural industries. Click here to pick your preferred podcast platform and subscribe so you never miss a new episode. As a bonus, that link contains every episode of The Office Hours w/me podcast, including all of Season 1.


Last week, I was Chicago’s NPR affiliate WBEZ talking about the best #Chicago sandwich you’ve likely never had and segregation in food media. You can listen to the full segment here.


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Office Hours with Ernest Wilkins is written and curated by Ernest Wilkins in Chicago, Illinois. He’s grilling the second the temp hits 42 degrees, just try and stop him.
Office Hours with Ernest Wilkins
Office Hours with Ernest Wilkins
Office Hours Magazine is a new take on the B2B publication, focusing on the business of cultural industries.