How this sample was chosenWe screened accessible, attributable DealBook columns published from February through December 2016 and selected six distinct medium- or long-term claims across financial technology, platform competition, public markets, encryption policy, presidential ethics and impact finance. Event reporting, one-off deal explanations, speculative worst cases and repeated versions of the same thesis were excluded.
01
Financial technology
Banks and fintech
Disruption thesis“Fintech firms would chip away at banks’ profitable franchises, with incumbents likely to buy the winners”
Sorkin was right that the threat would arrive service by service rather than as one dramatic bank replacement. Payments, lending and wealth products were unbundled, and regulators now treat bank–fintech partnerships as a permanent category. The acquisition ending was less tidy: many prominent platforms remained partners, vendors or competitors. Disruption came with an API, not necessarily a purchase agreement.
The New York Times · Apr. 7, 2016 ↗Observed realityPartialFintech captured important services and prompted extensive bank partnerships, but leading firms were not simply absorbedPartial
02
Platform economics
Uber
Capital and consolidation“Uber’s fundraising would force ride-hailing toward one or two leaders per market, and an IPO within three or four years”
Sorkin read the capital raises as territorial warfare: subsidise scale, narrow the field and eventually face public shareholders. Uber combined its China business with Didi weeks later and filed to go public inside the stated window. The empire remained regional rather than universal, but the financing logic arrived on schedule.
The New York Times / Business Standard · Jun. 21, 2016 ↗Observed realityHitUber exited China for a Didi stake and filed for its IPO in April 2019Hit
03
Capital markets
Public companies
Listing decline“Smart money would remain private and US public companies were becoming a dying breed”
The private-market diagnosis endured: companies can raise large sums and remain private far longer than the old script allowed. ‘Dying breed’ was theatrical accounting. SIFMA’s broader series counted 5,532 listed companies in the second quarter of 2026, above the roughly 4,100 figure cited in 2016, though definitions differ. Depleted, yes. Extinct, inconveniently no.
The New York Times · Jul. 21, 2016 ↗Observed realityPartialPrivate capital stayed structurally important, while a broad count reached 5,532 US-listed companies in 2026Partial
04
Technology policy
Apple and the FBI
Encryption settlement“One terrorist’s phone would not settle encryption; durable rules required legislation or public consensus”
Sorkin rejected the idea that either Apple or the FBI should decide the general rule through one emotionally loaded case. The Justice Department found another route into the device and vacated its demand. Congress was still publishing primers on the same encryption-versus-access argument in 2026. The phone was opened; the question remained locked.
The New York Times / Business Standard · Feb. 24, 2016 ↗Observed realityHitThe government unlocked that phone through a third party while the lawful-access dispute persisted for a decadeHit
05
Political economy
Trump business conflicts
Governance warning“Without credible independent oversight, Trump’s business empire would create untenable conflicts and opportunities to buy influence”
Sorkin proposed an independent corporate monitor because a presidency attached to hotels, licensing and foreign counterparties presented conflicts too numerous for promises. The monitor was not appointed and the assets were not divested. The Office of Government Ethics later said the arrangement was not blind and that nothing short of divestiture would resolve the conflicts. He predicted the problem, not the remedy.
The New York Times / Business Standard · Nov. 30, 2016 ↗Observed realityHitTrump did not divest; the federal ethics director said the arrangement failed the standards followed by recent presidentsHit
06
Investment industry
Impact investing
Institutional scale“TPG’s Rise Fund would move impact investing beyond charity by pairing measurable social outcomes with institutional capital”
The column’s wager was not merely that one $2 billion fund would close. It was that pension and sovereign capital could turn measurable impact into an investment product rather than a philanthropic annex. TPG now reports $32 billion under management across a scaled platform. Its impact measurements remain its own claims, but the institutionalisation is difficult to misplace.
The New York Times / Business Standard · Dec. 21, 2016 ↗Observed realityHitTPG expanded Rise into a $32 billion impact platform spanning more than 100 companiesHit
The Uber item is stronger than a lucky IPO date. He connected the financing strategy to market structure, consolidation and the eventual need to face public investors.
That mechanism is why it scores as a hit. We read ‘one or two per market’ literally, not as a prediction that Uber would become a single global monopoly.
Partial on public companies is sensible, but the count is definition-sensitive. Domestic operating companies, exchange listings and reporting issuers are not interchangeable populations.