Todd Ricketts — Chicago Cubs co-owner and founder of Freespoke, the search engine that labels news sources with media bias ratings — joins the Chuck Toddcast for a wide-ranging conversation that bridges the increasingly intertwined worlds of media, technology, and professional sports. Ricketts makes the case that when people are given genuinely good information from across the ideological spectrum, they tend to arrive at good answers — and that Freespoke's mission is to present all sides and then get out of the way, rather than letting ad sales determine what news you see. He pushes back on the idea that the market alone can solve the data privacy crisis, arguing data may eventually need to be regulated like a utility but that nothing changes until there's a major "event" that creates real public groundswell. Ricketts is candid about Freespoke's challenges — paywalls remain a real obstacle, the left/right labeling is imperfect and done by outside groups, and the political landscape itself is shifting in ways that scramble the traditional categories . He observes that podcasts have become a primary news source because people clearly hunger for long-form content with nuance, that politicians are now visibly afraid of giving long answers because they might get clipped, and that legacy media still doesn't seem to understand why its audience has migrated elsewhere.
The second half pivots into the business of running a baseball team, and Ricketts brings the same straight-talking pragmatism to MLB's looming economic crisis. He argues you cannot sell a salary cap to MLB owners without genuine revenue sharing, because if the league itself isn't competitive then everyone eventually loses — including the owners writing the biggest checks. Players currently take roughly 48% of revenue, a number he expects to climb to around 52% in the next deal, and Ricketts is honest that half of MLB's franchises are still essentially mom-and-pop operations even as private equity money is rapidly entering the sport. He talks about the difficulty of running any sports team in 2026 because fans genuinely feel like they own the franchise, why ownership groups are increasingly building entire entertainment districts around their ballparks to control the fan experience end-to-end, and the painful broadcast rights question every team is wrestling with: fans have cut the cord, the old TV economics no longer work, and ownership has to be flexible with new broadcast partners even as they ask themselves whether season ticket holders should be entitled to free access to every game. Ricketts closes by laying out what would qualify as a disappointing season for the Cubs — a sober assessment from an owner who has watched the economics of his sport, and the media landscape his business depends on, both transform at the same time.
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Timeline:
(Timestamps may vary based on advertisements)
00:00 Todd Ricketts joins the Chuck ToddCast
00:45 Providing media bias ratings for online news sources
03:15 When people are given good info, they come up with good answers
03:45 Goal is to present all sides, then let people make up their mind
05:00 You don’t want ad sales for search to determine your information
07:15 Can the market fix data sales, or does the government need to regulate?
09:00 Should data be regulated like a utility?
09:30 There will need to be an “event” to cause groundswell over data privacy
10:30 Does Freespoke labeling news left/right cause users to seek their preferred source?
13:30 Politics are shifting and what used to be a “left” issue is now a right issue etc
14:15 Protectionism has become right and free trade has become left
16:00 How would someone like George Will be labled?
17:30 Labeling is done by outside groups and the labeling isn’t perfect
18:00 The company is for-profit, sells ads and has subscription model
18:45 All the search is AI curated, but people curate the current events page
19:30 Bing and Google are the direct competitors
20:15 The Freespoke algorithm tries to strip out bias
21:45 Some topics get a ton of content from one side & none from the other
23:15 People are informing themselves via podcasts instead of legacy news
24:00 Legacy media needs to understand why audience is going elsewhere
25:45 Popularity of podcasts show people like long form content
27:00 Politicians are afraid of long answers & nuance in case they get clipped
27:30 Paywalls are a challenge for Freespoke, but sources are still included
28:30 Why are there left/right labels on sports coverage?
30:00 What is Freespoke’s position on mis and disinformation?
30:45 What does Freespoke 2.0 look like?
32:00 AI is only as good as the people & information that train it
33:00 Will you get into the newsletter business?
34:45 Can you sell a salary cap to MLB owners without total revenue sharing?
36:00 If the league isn’t competitive, then everyone will eventually lose
37:15 Players currently get 48% of revenue, may move up to about 52%
38:30 Running a sports team is hard because fans feel like they own the team
40:30 What have you learned from running the Cubs?
42:00 Half the teams are still mom & pop operations, but PE is coming in
43:15 Ownership wants to control fan experience, building entertainment districts
44:15 Should teams always be available on free TV?
44:45 Fans have cut the cord, have to be flexible with broadcast partners
46:30 Should season ticket holders be able to get all game broadcasts for free?
47:15 What would qualify this season as disappointing for the Cubs?
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