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L.2 · ADVANCED · 3 MIN

Capital Structure Arbitrage

Capital structure arbitrage is the trade of treating a single firm's bonds and equity as two markets pricing the same enterprise value, and acting on the spread when they disagree. The thesis is not that the firm is good or bad. It is that two markets looking at the same balance sheet have arrived at inconsistent answers — and that one of them is more right than the other, with a catalyst in view.

Quiz · 5 questions ↓
§ 01

The setup in plain language: a credit spread implies a distance to default and an asset volatility (via Merton-style structural models). The equity market implies a different distance to default through its own implied vol and price level. When the two diverge by enough — typically 20%+ on implied EV — the trade is to long the cheap claim and short the rich one in duration- and notional-matched size.

§ 02
Bond view of EVEquity view of EVTrade
Lower (wide credit spread)Higher (rich equity)Long bonds, short equity
Higher (tight credit spread)Lower (depressed equity)Short bonds, long equity — rare; usually a turnaround thesis
AlignedAlignedNo trade — do not invent disagreement to justify activity
§ 03
Implied EV from bonds ≈ (face debt) / (1 − expected loss given default) · (1 + risk premium)
§ 04

Worked example — Pelham Holdings stock implies an EV / EBITDA of about 11x. Pelham's seven-year senior unsecured bonds trade at a credit spread of approximately 4.5%, which under typical recovery assumptions implies an asset volatility around 25% — well above the 18% the equity options market is pricing. The trader's thesis: the bond market is absorbing PFAS regulatory exposure that the equity market has not yet priced. Trade construction: long Pelham seven-year bonds at a yield to maturity of about 7%, short Pelham equity at 0.6x the bond notional to neutralise duration on the EV mean-reversion. Catalyst: the PFAS class-action discovery deadline ninety days out, which the trader believes will surface 10-K disclosures the equity has not absorbed.

§ 05

What can break the trade: (1) the equity market is right — PFAS exposure is small, the credit spread tightens while the stock rises, you lose on both legs; (2) a change in the firm's capital structure (a refinancing, a buyback, a tender) re-prices both legs in ways your hedge ratios were not built for; (3) a liquidity event in either market forces you to unwind before convergence; (4) you are paid carry on one leg and pay carry on the other, and the carry differential turns negative. Always model carry across the holding period — not just the convergence payoff.

§ 06
Halton Industries' stock implies an EV close to its bonds' implied EV; both move together within a few percentage points across the cycle. A strategist pitches a long-bond / short-equity capital-structure arb on Halton. What is the most defensible response?
§ 07

Capital structure arbitrage rewards the trader who can say which market is wrong and why. Without a thesis on the asymmetry of information between bond and equity holders — different funding pressures, different mandates, different time horizons — the trade is a bet on coincidence. The market is happy to take that bet from you.

Five questions · AI feedback

Sit with the ideas.

Westmoor Optical's senior unsecured bonds trade at a yield implying a credit spread that is consistent with an EV / EBITDA of about 6x given typical recovery assumptions. Westmoor's stock trades at an implied EV / EBITDA of 12x. If you believe the bond market is pricing risk the equity market is missing, which trade expresses the view?

Why:
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