October 15 in business history: a refused subsidy, a $35 billion share swap, and 142 closing stores

Three 15 Octobers, three decisions paid for with what the business already had: a postage surcharge, a share of stock, and a retailer's own brands and buildings.

On 15 October 1932, J. R. D. Tata flew a two-passenger de Havilland Puss Moth from Karachi to Bombay with the first load of air mail — India's first scheduled commercial air service 12. The aircraft belonged to Tata Sons' aviation division, kept in the air by a subsidy the government had refused to pay 3.

The project came from Nevill Vintcent, a former RAF officer then touring India giving joy rides, and Tata Sons approved it only because the outlay was small: 200,000 rupees. Tata asked the government for a mail subsidy, as carriers elsewhere received. It declined, twice. So the service ran on the small stamp surcharge a sender paid to connect a letter to Imperial Airways' mail at Karachi 3.

Tata's account of the bet: "Vintcent and I had faith in the future of aviation and believed that if we came in at the beginning of an era we had a better chance ultimately to achieve growth and leadership in the field" 3.

There were no radio or navigation aids and no aerodrome at Bombay; the planes used the mud flat at Juhu and moved to Poona each monsoon, and passengers were so unusual that one sometimes sat on top of the mail bags 3. Within a year it was the example to copy: India's Directorate of Civil Aviation reported a first year of 100 per cent punctuality 3. The airline went public in 1946 as Air-India and was nationalised in 1953 3.

Decision mirror: Tata Sons bought the airline back on 27 January 2022, on a winning bid of ₹18,000 crore, about US$2.4 billion, made the previous October 24. The rebuild is priced by the year: in the twelve months to March 2026 the Air India group lost ₹22,238 crore — more than the bid that bought it — against ₹10,859 crore a year earlier 5. Its chairman, N. Chandrasekaran, calls it a five-to-ten-year job: "Every great airline in history was built over decades, not quarters" 5. A subsidy the government would not pay in 1932 is now an annual bill the size of the airline.

Chevron agreed to buy Texaco for about $35 billion in stock on 15 October 2000, creating ChevronTexaco, the world's fourth-largest oil company, and cutting an estimated 4,000 jobs in a year of record industry profits 6. Each Texaco share would convert into 0.77 of a Chevron share, under a merger agreement Chevron's own filing dates as of 15 October 2000 7.

The headline price was not the price. To clear the merger, Texaco had to give up its 44 per cent of Equilon Enterprises — four refineries, seven lubricants plants and about 65 terminals among its assets — and its 35 per cent of Motiva Enterprises, the two downstream ventures it ran with Shell and Saudi Refining 89. It also had to sell the Discovery pipeline, its share of the Enterprise fractionator at Mont Belvieu, Texas, and its European refining and marketing businesses, with the stakes parked in a trust so they could be sold apart from Chevron 8.

Closing took almost exactly a year. The merger completed on 9 October 2001, and the definitive sale agreements were signed on 12 December 2001 — Shell taking 100 per cent of Equilon, Shell and Saudi Refining 50 per cent each of Motiva 79. ChevronTexaco dropped the Texaco name in 2005 10.

Decision mirror: Chevron ran the same play 23 years later, and the expensive part had moved from assets to time. In October 2023 it agreed to buy Hess for $53 billion in stock — 1.0250 Chevron shares per Hess share, $60 billion including debt — planning to close in the first half of 2024 11. It closed on 18 July 2025, twenty-one months later, and only after a favourable arbitration outcome over Hess's 30 per cent of Guyana's Stabroek Block; the day before, the FTC lifted its restriction on Hess's chief executive joining Chevron's board 12. In 2000 the second price was paid in divested assets. In 2023 it was paid in the calendar.

Sears Holdings, a 125-year-old retailer and a Dow component from 1924 to 1999, filed for Chapter 11 in the Southern District of New York in the early hours of Monday 15 October 2018, on the day a $134 million debt payment fell due 1314. The petition put assets between $1 billion and $10 billion and liabilities between $10 billion and $50 billion, with more than 100,000 creditors 13.

Three decisions were announced the same day: Eddie Lampert, who had run the company since merging it with Kmart in 2005, stepped down as chief executive but stayed chairman; an Office of the CEO took over daily operations, with Mohsin Meghji as chief restructuring officer; and 142 stores — 79 Sears and 63 Kmart — were marked for closing 141516.

The cash to run the case came partly from the trouble's own source: $300 million of debtor-in-possession financing from the existing secured lenders, and a further $300 million under negotiation with Lampert's fund, ESL 1415.

For most of a decade the company had funded itself by selling itself. Lands' End was spun off, its best stores went into a new real estate investment trust called Seritage Growth Properties, Craftsman was sold to Stanley Black & Decker for $900 million in 2017, and in 2018 ESL proposed buying Kenmore and the home services business for $1.47 billion 1415.

What remained had shrunk on every measure: sales had more than halved while capital spending ran below 1 per cent of sales for five years, and the store count had fallen from about 3,500 at the 2005 merger to fewer than 700 1415. Lampert's fund won the January 2019 auction with a $5.2 billion bid, and in February a judge approved the sale of the most valuable parts of the company — 425 stores and about 45,000 jobs — to a new company, Transformco 16. Unsecured creditors including Simon Property Group objected that the estate had been stripped, and the pension insurer warned of a $1.7 billion gap 16.

Decision mirror: Seritage is the number to watch. Through 2025 it generated $230.7 million of gross proceeds and repaid $190 million of debt, leaving $50 million outstanding and about ten properties 17. In its March 2026 results it said the remaining proceeds and its cash would not cover its obligations, raising "substantial doubt about the Company's ability to continue as a going concern", with its term loan maturing on 31 July 2026 17. The real estate carved out of Sears to be worth more than Sears is nearly gone too.