⚠ Buying Back at the Top of the CycleModerate threat

Caterpillar (CAT) — threat to the moat

Caterpillar's rule of returning nearly all its free cash flow means it buys the most stock when its shares are dearest.

Caterpillar spent $5.0 billion on its own shares in the first quarter of 20261, in a year when the shares traded as high as $1,073.462. They closed at $805.25 in September3, about 25% below that high4.

Share repurchases ($M)3,79820184,04720191,13020204,97520237,69720245,19020255,000Q1 2026Caterpillar Forms 10-K FY2019, FY2022, FY2025; Q1 2026 release
Most bought when prices were highest.

A cyclical company buying heavily near the peak of its earnings and its multiple is the opposite of buying cheaply. In 2020, when profit halved, it spent $1,130 million5; in 2024, a record-profit year, it spent $7,697 million6. The buybacks follow the cash, and the cash is highest when the shares are dearest.

The policy of returning substantially all free cash flow7 makes this almost inevitable, because it commits the company to buy in good years regardless of price.

The company's own chart shows the tilt. The weighted average price it paid rose from $112 in 2020 to $205 in 2021, $256 in 2023 and $369 in 20258. The cheapest shares were bought in the year buybacks were smallest.

The price paid per share in 2026, when the company reports it, is the figure to judge. An average well above $369 would mean the largest buyback year came at the richest price.

References
  1. ReportedCaterpillar spent $5.0 billion on its own shares in the first quarter of 2026, in a year when the shares traded as high as $1,073.46.
    Caterpillar first-quarter 2026 results release, Form 8-K exhibit 99.1 - price realization and $5.0 billion of repurchases. — Q1 2026 · publ. 30 April 2026 · source ↗
  2. ReportedCaterpillar spent $5.0 billion on its own shares in the first quarter of 2026, in a year when the shares traded as high as $1,073.46.
    Caterpillar (CAT) market data - $805.25 at the close on 24 September 2026, market cap $370.15B, 52-week range 459.58-1,073.46, dividend $6.52 (0.81%). — September 2026 · publ. 24 September 2026 · source ↗
  3. ReportedThey closed at $805.25 in September, about 25% below that high.
    Caterpillar (CAT) market data - $805.25 at the close on 24 September 2026, market cap $370.15B, 52-week range 459.58-1,073.46, dividend $6.52 (0.81%). — September 2026 · publ. 24 September 2026 · source ↗
  4. Moat Explorer calcThey closed at $805.25 in September, about 25% below that high.
    Moat Explorer calculation from Caterpillar's reported figures ($ millions unless stated). Dealers: 41 + 109 = 150 (2025); 43 + 113 = 156 (2022); 46 + 119 = 165 (2019). Segment margins (segment profit / total segment sales, FY2025 10-K basis): Construction Industries 6,975 / 27,418 = 25.4% (2023), 6,165 / 25,455 = 24.2% (2024), 4,675 / 25,060 = 18.7% (2025); Resource Industries 2,836 / 13,669 = 20.7%, 2,538 / 12,471 = 20.4%, 1,988 / 12,474 = 15.9%; Power & Energy 4,936 / 28,001 = 17.6%, 5,736 / 28,854 = 19.9%, 6,418 / 32,201 = 19.9%; Financial Products 909 / 3,785 = 24.0%, 932 / 4,053 = 23.0%, 966 / 4,220 = 22.9%, 590 / 3,044 = 19.4% (2020). Recast (Rail in Resource Industries): 2,151 / 15,920 = 13.5% (2025), 2,676 / 15,745 = 17.0% (2024); Power & Energy 6,256 / 28,624 = 21.9%. Construction Industries H1 2026 3,482 / 15,507 = 22.5%. Implied Rail: sales 15,920 - 12,474 = 3,446 and profit 2,151 - 1,988 = 163, 163 / 3,446 = 4.7% (2025); sales 15,745 - 12,471 = 3,274 and profit 2,676 - 2,538 = 138 (2024). Power generation 10,275 / 3,963 = 2.6 times (2020-2025); 10,275 / 67,589 = 15.2% of sales and revenues; three times the 2024 base 7,756 x 3 = 23,268. Oil and gas 7,502 / 27,143 = 27.6% of Power & Energy external sales; 7,502 / 3,701 = 2.0 times. Services 24 / 67.589 = 35.5%; (30 / 24)^(1/5) - 1 = 4.6% a year. Backlog 72.1 / 30.0 = 2.4 times; long end 29.2 / 19.3 - 1 = 51%. Customer advances 4,777 / 3,314 - 1 = 44%. Price realization H1 2026 426 + 595 = 1,021; 2024 against 2023 1,238 / 5,596 = 22%. Volume H1 2026 2,318 + 3,113 = 5,431. Capex excluding leased equipment 2,821 / 1,597 - 1 = 77%. Pre-tax return on average MP&E net assets (MP&E adjusted operating profit / average MP&E net assets): 4,675 / 20,070 = 23.3% (2020), 6,453 / 19,662 = 32.8% (2021), 8,656 / 19,841 = 43.6% (2022), 13,439 / 19,450 = 69.1% (2023), 13,246 / 19,999 = 66.2% (2024), 11,327 / 21,417 = 52.9% (2025). Profit 8,884 / 6,147 - 1 = 44.5% and diluted EPS 18.81 / 10.26 - 1 = 83.3% (2018-2025). Dividends paid 2,749 / profit 8,884 = 30.9%. Return on average equity 8,884 / ((19,494 + 21,318) / 2) = 43.5%. Price to earnings at year end (market capitalisation $bn / profit $bn): 39.57 / 2.512 = 15.8 (2015); 93.75 / 0.754 = 124.3 (2017); 74.98 / 6.147 = 12.2 (2018); 81.62 / 6.093 = 13.4 (2019); 98.88 / 2.998 = 33.0 (2020); 111.83 / 6.489 = 17.2 (2021); 124.67 / 6.705 = 18.6 (2022); 150.52 / 10.335 = 14.6 (2023); 175.14 / 10.792 = 16.2 (2024); 268.09 / 8.884 = 30.2 (2025); trailing 370.15 / 10.844 = 34.1. Share price 805.25 / 1,073.46 - 1 = -25%. Trailing twelve months to June 2026: sales and revenues 67,589 - 30,818 + 37,958 = 74,729; profit 8,884 - 4,182 + 6,142 = 10,844; diluted EPS 18.81 - 8.82 + 13.23 = 23.22. Debt at 30 June 2026 5,046 + 35 + 8,026 + 10,655 + 21,384 = 45,146; at 31 December 2025 5,514 + 35 + 7,085 + 10,678 + 20,018 = 43,330; Financial Products debt 5,514 + 7,085 + 20,018 = 32,617, 32,617 / 43,330 = 75%. Financial Products segment assets 41,476 / 64,392 = 64%. Downturns: 38,537 / 47,011 - 1 = -18% (2016); 41,748 / 53,800 - 1 = -22% (2020). Construction Industries Asia/Pacific external sales 3,783 / 4,390 - 1 = -14%; North America share 14,064 / 24,800 = 57%. Shares of 2025 sales and revenues of 67,589: Construction Industries 24,800 = 36.7%; Resource Industries 12,185 = 18.0%; Power & Energy 27,143 = 40.2%; Financial Products 4,220 = 6.2%; Construction and Resource together (24,800 + 12,185) / 67,589 = 54.7%. Segment external sum 27,143 + 24,800 + 12,185 + 4,220 = 68,348 against 67,589 (difference 759, All Other +46 and corporate items -805); 2024 25,344 + 12,100 + 24,088 + 4,053 = 65,585 against 64,809 (776); 2023 27,294 + 13,329 + 23,355 + 3,785 = 67,763 against 67,060 (703). Power & Energy share 27,143 / 68,348 = 39.7%. 2030 range: 64,809 x 1.06^6 = 91,933; 64,809 x 1.09^6 = 108,691. RPMGlobal 733 / 67,589 = 1.1%. Autonomous trucks 827 / 690 - 1 = 20%; 690 x 3 = 2,070. Tech-enabled machines 500 / 191 = 2.6 times. Latin America employees 22,300 - 19,700 = 2,600 (EAME 16,700 - 15,900 = 800; Asia/Pacific 26,900 - 25,300 = 1,600; North America 52,100 - 52,000 = 100). Profit 2025 8,884 / 10,792 - 1 = -17.7%. Cost of goods sold 44,752 / 40,199 - 1 = 11.3%. Financial Products segment assets 41,476 / 36,925 - 1 = 12.3%. Power generation growth 7,756 / 6,362 - 1 = 21.9%, 10,275 / 7,756 - 1 = 32.5%. Engine capex at 4% to 5% of 2025 machinery, power and energy sales of 63,980: 2,559 to 3,199. Earnings implied by forward and trailing P/E 34.70 / 28.01 - 1 = 24%. Analyst target 975.61 / 805.25 - 1 = 21%. Segment capex 2025: Construction Industries 358 + Resource Industries 626 = 984, against Financial Products 1,341. Power & Energy Q2 2026 external sales: North America 4,182 against other regions 373 + 1,348 + 892 = 2,613 - valuation, balance sheet, capital returns and returns on capital. — 2015-2026 · publ. September 2026 · source ↗
    Method: Arithmetic on figures reported in Caterpillar's Forms 10-K, 10-Q, results releases, the March 2026 recast exhibit, the February 2026 Barclays deck, the earnings calls and market data; operands shown in the source line.
  5. ReportedIn 2020, when profit halved, it spent $1,130 million; in 2024, a record-profit year, it spent $7,697 million.
    Caterpillar Form 10-K for fiscal 2022 - segment sales and profit for 2020-2022, the dealer count, sales by application, and the $925 million Rail goodwill impairment. — FY2022 · publ. February 2023 · source ↗
  6. ReportedIn 2020, when profit halved, it spent $1,130 million; in 2024, a record-profit year, it spent $7,697 million.
    Caterpillar Form 10-K for fiscal 2025 - Item 1 business: history, products, Cat Financial, employees and order backlog. — FY2025 · publ. 13 February 2026 · source ↗
  7. ReportedThe policy of returning substantially all free cash flow makes this almost inevitable, because it commits the company to buy in good years regardless of price.
    Caterpillar Form 10-Q for the quarter ended 30 June 2026 - backlog, outlook, tariffs, dealer inventory, balance sheet and the RPMGlobal acquisition - financial statements and notes: balance sheet, cash flow and the RPMGlobal acquisition. — Q2 2026 · publ. 5 August 2026 · source ↗
  8. ReportedThe weighted average price it paid rose from $112 in 2020 to $205 in 2021, $256 in 2023 and $369 in 2025.
    Caterpillar presentation for the Barclays fireside chat, 18 February 2026 - Investor Day targets, services, MP&E free cash flow, share count, buyback prices and the OPACC reconciliation. — 2019-2025 · publ. 18 February 2026 · source ↗
Sources
Generated September 25, 2026