Evidence from 2022–2025 shows that the SEC did, in fact, embark on a multi‑year wave of enforcement actions against a wide range of crypto firms and related investment entities over tokens the agency characterizes as securities, producing substantial settlements and extended litigation.

Key points:

1. Sustained surge in SEC crypto enforcement (2022–2025)
   Independent analyses show that SEC crypto‑related enforcement actions hit a record high in 2023, with 46 actions—up 53% from 2022 and nearly double 2021. Monetary penalties against digital‑asset market participants totaled about $2.89 billion by the end of 2023, with $281.4 million in 2023 alone; the majority of cases involved unregistered securities offerings and related violations. (fortune.com)
   The SEC’s own FY 2023 enforcement summary highlights a “series of enforcement actions” targeting “rampant noncompliance in the crypto asset intermediary space,” naming platforms such as Beaxy, Bittrex, Binance, and Coinbase. (sec.gov)
   The SEC’s running list of crypto‑asset enforcement actions shows a steady cadence of new cases through late 2023 and 2024 (e.g., Kraken, BarnBridge DAO, ShapeShift AG, Abra/Plutus, various trading and mining schemes, and others), consistent with Jason’s “one firm after another” framing. (sec.gov)

2. Enforcement reaching investment/venture‑style crypto firms and related parties
   Jason’s prediction mentioned venture players and related parties. While the most high‑profile cases hit exchanges and issuers, the SEC did bring actions against crypto‑focused private funds and managers. A prominent example is Galois Capital Management LLC, a former registered investment adviser to a private fund that primarily invested in crypto assets. In 2024, the SEC charged Galois with custody violations involving “crypto assets being offered and sold as securities” and misleading investors about redemption terms; Galois agreed to a civil penalty as part of a settlement. (sec.gov)
   Combined with actions against DAOs (BarnBridge), DeFi projects, and centralized platforms that listed or structured products around tokens the SEC alleges are securities, this matches the spirit of going after the ecosystem of venture‑style and intermediary actors around such tokens, not only the token issuers themselves. (viewpoints.reedsmith.com)

3. "Massive settlements" did occur (often alongside or in addition to SEC actions)
   Within the 2022–2026 prediction window, there were multiple large monetary resolutions connected to crypto enforcement:

   • Kraken (Payward Ventures & Payward Trading) settled with the SEC in February 2023: it ended its U.S. staking‑as‑a‑service program and agreed to pay $30 million in disgorgement, interest, and penalties over allegations its staking program was an unregistered securities offering. (sec.gov)
   • BarnBridge DAO and its founders agreed in December 2023 to pay more than $1.7 million and shut down the DAO’s SMART Yield products, which the SEC characterized as unregistered structured crypto‑asset securities. (sec.gov)
   • In parallel, broader U.S. enforcement against Binance (DOJ, CFTC, Treasury) produced an enormous $4.3 billion global settlement in November 2023. While this was not an SEC case, it occurred alongside—and in the shadow of—an SEC civil suit alleging securities‑law violations by Binance and its founder, underscoring the “massive settlements plus SEC litigation” environment Jason described. (cftc.gov)

4. Multi‑year litigation over whether many tokens are securities
   From late 2022 onward, multiple SEC suits over token‑as‑security theories have dragged on for years:

   • The SEC’s longstanding case against Ripple (filed 2020) continued to generate key rulings in 2023 and beyond and remained active into the prediction window. (ccn.com)
   • The SEC sued Coinbase and Binance in 2023, alleging they operated as unregistered securities exchanges and listed numerous tokens the SEC claims are unregistered securities; those cases proceeded through extensive motion practice and, for Binance, a 2024 ruling allowing most of the SEC’s claims to go forward. (sec.gov)
   • As of early 2025, analyses still list multiple ongoing SEC crypto lawsuits—Ripple, Kraken, Cumberland DRW, Pulsechain—plus several open investigations, even as the agency begins to retreat from some cases under new leadership. (coindesk.com)
     This pattern of overlapping cases running for years (often initiated 2020–2023 and still unresolved by 2025) fits Jason’s forecast of “three or four years of litigation.”

5. Timing vs. prediction window
   Jason spoke in July 2022 about the next 3–4 years (roughly 2022–2025/26). We are now in November 2025, more than three years into that window. The record‑setting wave of crypto enforcement actions in 2022–2024, the substantial settlements, and the fact that several high‑impact cases remain active in 2025 collectively show that this prolonged enforcement‑and‑litigation cycle did materialize within the predicted timeframe. (fortune.com)

Caveat: The normalized version of the prediction (explicitly emphasizing traditional “venture firms”) is somewhat narrower than Jason’s original wording, and truly marquee SEC cases against name‑brand Sand Hill Road VC funds have not (as of late 2025) been a central feature of the crackdown. But taken in context—SEC going after a broad array of crypto firms, funds, DAOs, and intermediaries with token‑as‑security theories, producing big settlements and drawn‑out litigation over several years—the core substance of his forecast has clearly played out. Hence the prediction is best judged as right, albeit directionally rather than perfectly precise on which specific types of firms would be most in the crosshairs.