The prediction hinges on whether future AI–publisher content-licensing deals, on average, exceed the ~$20M/year level of the cited New York Times deal.

1. Baseline deal (~$20–25M/year)
In late July 2025, reporting revealed that Amazon’s multiyear AI licensing deal with The New York Times is worth $20–25 million per year, allowing Amazon to train its AI models and surface NYT content in products like Alexa. This is the specific deal and order of magnitude the podcast referred to as the starting point.【2news12】【2search3】

2. Pre‑existing context already spans well above and below $20M/year
Before this NYT–Amazon disclosure, major media–AI deals already covered a wide value range, including:

• OpenAI–News Corp: reported $250M+ over five years (≈$50M/year) for access to WSJ, NY Post, and other News Corp outlets.【0search10】【0search9】
• Google–Reddit: about $60M per year for content used in AI and search.【0search3】
• Several other OpenAI publisher deals (Axel Springer, Financial Times, Dotdash Meredith, etc.) where only partial or rough figures (often “tens of millions” total or $5–10M/year ranges) are public.【0search3】【0search10】
  This shows that even before the NYT–Amazon benchmark, deal sizes were not uniformly trending around $20M/year; they ranged both above and below it.

3. Post–Aug 1, 2025 deals rarely disclose comparable dollar amounts
After the podcast (Aug 1, 2025) and up to Nov 30, 2025, there are new AI–publisher arrangements, but their effective annual economics are not disclosed:

• Gannett (USA TODAY Network) – Perplexity: strategic AI content-licensing deal plus ad‑revenue share; no dollar figures given.【5search1】【5search3】【5search8】
• Perplexity’s Comet Plus model: a $42.5M initial revenue pool to be shared across participating publishers, with plans to grow over time—again, a pool and rev‑share, not clear per‑publisher annual license numbers.【5news12】
• People Inc. (formerly Dotdash Meredith) – Microsoft and Gannett – Microsoft: participation in Microsoft’s new Publisher Content Marketplace, a pay‑per‑use / marketplace model rather than a disclosed fixed yearly check.【3news13】【3news14】【3search1】【3search3】【3search8】
  None of these provide transparent, per‑year dollar figures comparable to the NYT–Amazon arrangement.

4. Why the prediction can’t be scored yet
Jason’s claim is about a future trend in average dollar values for similar AI–major‑publisher licensing deals relative to the ~$20M/year NYT benchmark. To test that, we’d need:

• A meaningful set of post‑July‑2025 deals of similar type (AI company ↔ major publisher), and
• Clear, per‑deal financial disclosures so we can compare whether the average annualized value is rising or falling.

As of Nov 30, 2025:

• Only a few months have elapsed since the baseline NYT–Amazon numbers became public.
• Most subsequent AI–publisher deals either don’t disclose dollar values or use rev‑share/marketplace structures whose realized annual payouts aren’t yet known or reported.
• There is no robust data set from which to compute or qualitatively assess an “average” trend above or below $20M/year.

Because of the short time horizon and the lack of sufficient, comparable post‑baseline deal data, we cannot determine whether the average value of such deals is actually trending up or down relative to the ~$20M/year benchmark. The prediction therefore remains too early to evaluate, not clearly right or wrong.