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Thomas S.Y. HO
New York Umverslty, New York, NY 10006, USA
Ronald F. SINGER
Vmverslty ofHouston, Houston, TX 77004, USA
This paper exammes the effect of alternative bond indenture provrslons on the allocation of risk
among the firms clatmants. The approach taken here differs from that of earlier studies m that
risk allocation 1s examined while the firms leverage (m market value terms) is held constant In
this context, four indenture provrsrons are examined (1) the time to maturity, (2) the promised
payment schedule, (3) financing restrictions and (4) priority rules. It 1s concluded that nsk is
transferred from stockholders to bondholders as the time to maturity and promised payment
increase appropriately. Furthermore substitution of longer-term debt for an equal amount of
shorter-term debt also increases the nsk to bondholders while decreasing the nsk to
stockholders The analysis shows that a coupon bond can be represented by a unique discount
bond wrth the same nsk and value. This permits the charactenzatlon of the effective maturity of
a risky debt issue, a concept analogous to the stochastic duration of a default-free coupon bond.
These results are shown to be independent of the means used to finance the debt issue. Fmally,
it 1s concluded that the relative risk associated with different bonds issued by the same firm
cannot be determined by the structure of priority rules alone It 1s also necessary to consider the
timing of the promised payments compared to that of the other debt Issues m the firms capital
structure
1. Introduction
Since the seminal work of Modighani and Miller (1958) capital structure
theorists have concentrated on the impact of leverage on the allocation of
risk between bondholders and stockholders. These investigations (often
implicitly) impose an arbitrary set of indenture provisions, and concentrate
on the risk of the debt and equity claims as the market value of the debt
changes. On the other hand, mvestigations explicitly dealing with the effect
of alternative indenture provisions typically utilize a comparative statics
*The authors wish to thank Michael Jensen, Avner Kalay, Clifford Smith, Jr. and the referee
for then helpful comments.
In a perfect market setting, Hamada (1972), Rubmstem (1973) and Chen (1978), have
considered these issues
Y= (dD/d V(I/lD),
where I/ is the market value of the firm and D is the market value of the
debt. Merton (1973) shows that this is an appropriate measure of risk, in the
Rothschild-Stiglitz (1970) sense for contingent claims models.4
(A.l) There are no taxes, transaction costs or other frictions, so that the
value of the firm is independent of its capital structure [Modigliani and
Miller (1958)].
41n a portfoho context, an assets beta is an appropriate measure of risk Galai and Masuhs
(1976) show that bD= V/J, where Pn 1s the debts beta and /Iv 1s the firms beta Therefore, a
bonds elastlclty is a measure of risk relative to the risk of the firm
378 TS Y Ho and RF Smger, Bond indentures and rwk
dV/V=crdt+odw,
(1) The increased promised payment raises the maximum value of the firm
at which it defaults.
(2) The longer maturity increases the expected value of the firm at maturity.
(3) The longer the maturity the greater the variance of the value of the firm
at maturity.
This section considers the net impact of these effects.
Default can be remedied either by amendmg the contract, or by fihng for bankruptcy
Bankruptcy IS a legal process, which IS concluded either by reorganization or hqmdatlon [see
Smith and Warner (1979)]
TS Y Ho and RF Smgdr, Bond mdentures and rusk 379
D=VN(z-o&)+Fe-N(-z), (34
and
(3.2)
where
(3.3)
N(x)= j f(s)ds
-CX
is the standard normal density. Note that N(z) is the risk-neutral probability
of default. Theorem 1 describes the relationship between the debts elasticity
and its time to maturity.
Theorem 1. The relationship between the elasticity of a discount bond and its
maturity, when its pormised payment is adjusted to hold the market value of the
bond constant, is as follows:
(i) The elastictty is an increasing function of time to maturity.
(ii) The elasticity approaches one as time to maturity goes to infinity; it
approaches zero as the time to maturity gets arbitrarily small.
time to maturity holding the market value of the debt unchanged. When
maturity changes, the debts promised payment must be adjusted to assure a
constant debt value. That is, eq. (3.4) must hold:
(3.4)
-~f(z-~&)Vd&2F~N(-z)e-r&d&+N(-z)e-dF=0. (3.5)
eJ;-f~*j,-(a&dz + zad&--a&d&)=e-dF-Fre-2fid.&.
(3.6)
Eqs. (3.5) and (3.6) can be used to eliminate dF; and simplifying gives the
relationship between dz and d& as
Note that dz/dfi>O, since f(z)/N( -z) >z [Kendall and Stuart (1977, p.
159)]. That is, given the market value of the debt, the probability of default is
positively related to maturity.
Finally, eq. (3.2) relates the elasticity explicitly with z and r. Differentiating
(3.2) gives
dy = (V/D)f(z
- o&)(dz - crd&). (3.8)
Notice that the leverage ratio (D/V)is constant by the design of the problem.
Using eqs. (3.7) and (3.Q dz can be eliminated and it follows that
(3.9)
Part (i) of the theorem follows immediately from (3.9). Since f(z)/N( -z)>z
for all values of z, dq/dz > 0 for any value of z, z and D/E
TS Y Ho and R.F Smger, Bond mdentures and ruk 381
Part (ii) requires that hm,,, y = 1 and lim,,, q =O. The proof first
establishes the relationship between z and r.
From the bond valuation equation, eq. (3.1),
ao/az=~f(z-oJz)-Fe-*f(-z)=O,
so that
(D/i+N(z-CT&) N(-z)
(3.10)
f(z-o&l =f(z>-
Eq. (3.10) relates z and z. Therefore it gives the asymptotic behavior of z as r
goes to infinity so that lim,,, r] can be examined. Appendix A shows that as
z-+00, (z-c& z converges to a value x,, such that N(x,) = O/l/: Since
ratios less than one, the argument goes the other way and elasticity increases
with maturity.
In their derivations Merton holds quasi-debt constant and Galai and
Masulis and Chen hold the promised payment constant. As a result an
increase in maturity reduces the market value of the debt. In contrast,
Theorem 1 holds the market value of the debt constant, implying an increase
in quasi-debt (that is as maturity increases, the offsetting promised payment
is increased at a rate exceeding the riskless rate of interest). Note that for
short maturities when the market valued leverage ratio is low, the debt will
be close to riskless so that quasi-debt approximates its market value. In this
case, Mertons result is consistent with Theorem 1. However, as the time to
maturity lengthens the debt becomes risky. It follows that bond elasticity
increases faster when the market value of the debt is held constant since
quasi-debt must increase. Furthermore, Theorem 1 shows that bond elasticity
is always an increasing function of maturity. For high leverage ratios, the
rate of increase in the promised payment exceeds the riskless rate. This
increase in quasi-debt more than offsets the risk reduction that would occur
if quasi-debt (or promised payment) were held constant.
Part (ii) of the theorem shows that the debt, at all leverage ratios, becomes
riskless (n+O) as the time to maturity gets arbitrarily small and approximates
unlevered equity (q+l) as the time to maturity tends to inlimty. This can be
explained by examining the behavior of the promised payment as maturity
goes to these limits. As a contingent claim, the market value of the debt is
always less than the value of the firm. Furthermore, as the time to maturity
gets small, the promised payment converges to the given market value. Thus
for a maturity arbitrarily close to zero, the promised payment must be less
than the value of the firm and will surely be paid. On the other hand, as time
to maturity increases, so must the promised payment. The equity component
of the debt increases, so that it behaves more like unlevered equity.
For a given leverage ratio, a change of debt maturity effects a change in
risk allocation between bondholders and stockholders. Theorem 1 focuses on
the risk to bondholders, and the following corollary describes the risk to the
stockholders:
Corollary. The elasticity of the equity, qE, in a firm with a single discount
bond behaves as follows:
Fig. 1 summarizes the results of Theorem 1 and its corollary. Notice that
as maturity goes to zero, the debt becomes riskless and the equitys elasticity
tends to 1 +D/E. This expression is thei familiar leveraging effect associated
Elasticity
Fig. 1 The elasticity of debt and the elasticity of equity as functions of the discount bonds
maturity (7) It IS assumed that the firms capital structure consists of eqmty and a discount
bond, and that the debt to eqmty ratlo (D/E) IS held constant
384 lXY Ho and R.F Smger, Bond mdentures and risk
7Both Hamada (1972) and Rubmstem (1973) consider equity risk m the context of a smgle-
period Capital Asset Pricmg Model. Hamada (1972) investigates the risk of eqmty m the
presence of risky debt, whereas Rubmstem (1973) considers the case of nskless debt In both
papers, beta 1s used as the measure of risk
T.S.Y; Ho and R.F Smger, Bond
Elasticity
Fig. 2. The elasttcrty of debt and the elasticity of equity as functions of the time to maturtty (z)
and the debt to equity ratio (D/E). It is assumed that the firms capital structure consists of
eqmty and a discount bond The surface QEEE represents the elasticity of equity, and the
surface DDD represents the elasticity of debt. The plane EFG represents an elasticity of unity
This section provides some insight into the concept of the crisis at maturity
as discussed in Johnson (1967). It is argued that the probability of default is
greatest at maturity, so that low-grade debt becomes riskier as the time to
maturity increases. This argument applies to an existing bond (with a given
promised payment) as the time to maturity approaches. Theorem 1 and its
corollary indicate that this argument cannot be used when considering the
risk of alternative bonds issued by the same firm. If both bonds market
386 TS Y Ho and R.F Swzger,Bond indentures and yuk
values are equal, then the one with the longer maturity is more risky. In fact,
by the corbllary, the crisis at maturity, in this context, is imposed on the
firms stockholders rather than its bondholders. For example a continuing
policy of rolling over short-term debt is more risky to stockholders than a
policy of issuing the same amount of long-term debt initially.
Unlike the dase of a single discount bond, the value and behavior of a bond
package depends on the means used to finance the early payment [Black and
Cox (1976)]. This section focuses on the behavior of the total debt package
as distinct from that of the component issues comprising the package. Thus
it is not necessary to consider the priority rules associated with the
component debt issues. The effect of the structure of priority rules on the risk
of the individual issues awaits development in section 6.
Geske (1977) derives the leverage ratio and the elasticity of the debt as
functions of the firms business risk, the timing and the amount of the
promised payments, the instantaneous riskless rate of interest and the
current value of the firm. For simplicity, it is assumed that the date of the
long-term promised payment is twice that of the short-term promised
payment (i.e., T, =iTL = T).
TS Y Ho and RF Singer, Bond mdentures and vtsk 387
(4.1)
(4.2)
(4.3)
y=a--x, (4.5)
where
fL= FL/VerTL
fs = FS/VerTs
is the short-term quasi leverage ratio. Given the current value of the firm, eqs.
(4.1H4.5) determine the value and elasticity of a bond package consisting of
two discount bonds, with promised payments F, and FL, maturing at T, and
TL, respectively.
The parameter &j,determined by (4.3), gives the bankruptcy state at T,, and
N(E) is the risk-neutral probability of default at T,. Parameter a is the
bankruptcy state at TL, and N(y) is the risk-neutral probability of default at
TL, conditional on the state variable x determined at T,. B(x), in (4.4),
represents the Ts value of the long-term debt conditional on x (assuming the
short-term payment is made).
388 TS Y; Ho and R.F Smger, Bond zndentures and risk
Within the context of the above model, long-term debt is substituted for
short-term debt. An increase m one promised payment alone increases both
the risk and market value of the debt. On the other hand, reducing the other
payment alone decreases the risk of the package.
The relative amount of long-term debt is characterized by the ratio fLlfS,
defined as the long-term debt intensity of the debt package. This measure is
proportional to the ratio of the promised payment to long-term bondholders
relative to the promised payment to short-term bondholders (the constant of
proportionality being edrT). Furthermore, the market value of long-term
debt, as a proportion of the market value of the total debt package, is an
increasing function of long-term debt intensity. Thus, an increase in long-
term debt intensity implies an increase in long-term debt relative to short-
term debt, both in terms of the bonds promised payments and in terms of
their market values. Theorem 2 examines the net effect of changes in long-
term debt intensity on the risk of the debt.
d(D/V)=N(-5)df,+ (4.6)
Furthermore, d{, dfS and dfL are related by the bankruptcy condition at Ts
[eq. (4.3)]. Differentiating (4.4) with respect to the three parameters l, fs and
fL gives this relationship as
m
JfW(-y)dx
ofi eeu~~-t-uTN(o~-a+~)dt-N(~-a)dfL=-r N(_i) dfL.
(4.7)
TS I: Ho and RF Swgev, Bond Indentures and rusk 389
(4.8)
Now, dt and df, can be eliminated by substituting (4.6) and (4.7) into (4.8),
and simplifymg, so that
(D,T/)ofi(dv/df,)
=f(tW(5 - 4 -& 7fWW -4 dx
+ 4<f(x)f(a - 4 dx
= d44 5). (4.9)
Thus,
Eq. (4.10) gives the effect of small changes in the firms long-term debt
intensity while holding leverage unchanged. Appendix B establishes that
4(u, 5) 1s positive for all values of a and t. Q.E.D.
That is, when there is no long-term debt, the risk of the debt package is
insensitive to the substitution of a small amount of long-term promised payment
for short-term promised payment, whtle keeping leverage unchanged,
That is, when there is no short-term debt, the sensitivity of the risk of the debt
package to substitution of short-term promised payment for a small amount of
the long-term promised payment can be significant, depending on the leverage
ratio.
lim N(5-a)N(-_)=iV(-5).
67-02
392 TS.Y Ho and R.F Smger, Bond mdentures and risk
Finally, f(&N(--l)<t for all values of <. Thus the first term on the r.h.s. of
(4.9) converges to 0. Furthermore,
Thus the first term on the r.h.s. of (4.8) converges to 0. Furthermore, from
(4.1 l),
5. Financing restrictions
Using assumptions (A.lHA.4) (A.7) and (A.9), eq. (5.1) describes the
leverage ratio as
These assumptions are imposed to neutralize the investment dectsrons impact on the total
rusk of the firm. This isolates the Impact of the sale of assets on the relative rusk of the financral
claims issued by the firm. The assumptions hold d the pnce of the assets equals its present value,
the risk of the sold assets equals the risk of the firm, and the assets return IS perfectly correlated
wrth the return of the firm.
394 T.S I7 Ho and R F. Smger, Bond indetures and mk
(5.3)
Proof. The basic idea of the proof is similar to that of Theorem 2. When
the long-term promised payment increases (dfL > 0), the short-term promised
payment has to be adjusted downward so that the debts value remains
constant. Consequently, bankruptcy states z and y would be affected (dz #O
and dy # 0).
lXY Ho and RF. Smger, Bond mdentures and mk 395
To account for the interrelationship among the four components (dz, dy,
df,, dfL) in differentiating eq. (5.1), the following equation has to hold:
Substituting eqs. (5.6) and (5.7) into eq. (5.8) and simplifying, it can be shown
that (details are given in appendix C)
lim i N(-x(h))f(a-h)dh=O.
a-rm -00
It follows that
lim dy/dfL = 0.
a-r-m
396 TS Y Ho and RF. Smger, Bond mdentures and rwk
Thus, the risk is insensitive to the change of long-term debt intensity when
there is no long-term debt. On the other hand, a direct calculation shows
that, from eqs. (5.9) and (5.10), @(O,u)>O, so that the debt packages risk is
sensitive to the change in the long-term debt intensity when there IS no
short-term debt. Q.E.D.
where y, ys and ~~ are the elasticities of the total debt package, the short-
term debt and the long-term debt, respectively. D,/D and D,/D are the
market values of short-term and long-term debt respectively, as proportrons
of the market value of the total debt.
TS Y Ho and R.F Smger, Bond indentures and rusk 397
The following sections describe the risk of the component issues as the
debt packages long-term debt intensity changes.
This section considers the allocation of the risk of the debt package
between a short-term senior and a long-term Junior debt issue as the effective
maturity of the debt package increases. It has been established, in Theorem
3, that the risk of the debt package is an increasing function of effective
maturity. Thus the elasticity of the debt package can be represented by the
curve AB in fig. 3.
Elasticity of Each
Debt Issue
Maturity
Fig 3 The debt package consists of two discount bonds: one maturing at q (short-term debt)
and the other maturmg at TL (long-term debt) The effective maturity of the debt package IS the
maturity of the discount bond havmg the same elastlclty and value as the debt package The
value of the debt package IS assumed to remam constant The elastlclty of long-term Jumor debt
IS given by curve GB The elastlclty of short-term semor debt IS given by curve AC The
elastlclty of the debt package IS aven by curve AB
function of effective maturity (Theorem 3), so is the risk of the senior short-
term issue. The risk of the semor issue can be represented by curve AC in fig.
3. As effective maturity goes to Ts, long-term debt goes to zero and the risk
of the short-term senior issue goes to the risk of the package. As the effective
maturity goes to TL, the value and risk of the short-term debt go to zero.
The risk of the long-term junior debt can now be derived for all effective
maturities between Ts and TL. Its elasticity is represented by curve GB m fig.
3. Since the allocation of risk obeys eq. (6.1), the elasticity of the long-term
junior debt is a decreasing function of effective maturity. It converges to the
elasticity of the debt package as effective maturity goes to TL. As one would
expect, the senior issue is less risky than the junior issue for all levels of
effective maturity.
i%rticity of Each
Debt Issue
Elasticity
of long-term
Effective
7 Maturity
0 TL
Fig 4 The debt package consists of two drscount bonds one maturing at Ts (short-term debt)
and the other maturing at TL (long-term debt) The effective matunty of the debt package IS the
maturity of the discount bond havmg the same elastmrty and value as the debt package The
value of the debt package IS assumed to remam constant The elastrctty of long-term semor debt
1s given by curve OGB The elastrnty of short-term mmor debt IS given by curve ADGC The
elastmrty of the debt package IS given by curve AGB The senior debt and Jumor debt have the
same elastrcrty when the effective maturity of the debt package IS zO, and the elastrctty of the
short-term nnnor debt reaches the maximal value at D.
is long-term, then the results are less obvious. It can no longer be argued
that senior debt is inherently less risky than the subordinated debt in the
same firm. This is because jumor short-term debt will almost certainly be
paid in full as long as the promised payment to this debt is sufficiently small.
If the firm adds short term debt, its risk will increase, reaching an interior
maximum. Thereafter, further increases in short-term junior debt, while
holding leverage unchanged, tends to reduce the risk of that debt issue. This
IS a consequence of the decrease in the senior claims as the firm substitutes
short-term for long-term. This reduces the amount of prior claims associated
with the short-term debt, tending to reduce its risk.
7. Conclusions
differs from that of earlier studies in that risk allocation is examined while
the firms leverage (in market value terms) is held constant. In this context,
four indenture provisions are examined: (1) the time to maturity, (2) the
promised payment schedule, (3) financing restrictions, and (4) priority rules.
This approach provides additional insight mto the impact of these
indenture provisions on the allocation of risk. It is concluded that risk is
transferred from stockholders to bondholders as the time to maturityand
promised payment increase appropriately (Theorem 1). Furthermore
substitution of longer-term debt for an equal amount of shorter-term debt
also increases the risk to bondholders while decreasing the risk to
stockholders (Theorem 2). The analysis shows that a coupon bond (or a
package of discount bonds) can be represented by a unique discount bond
with the same risk and value (Theorem 3). This permits the characterization
of the effective maturity of a risky debt issue, a concept analogous to the
stochastic duration of a default-free coupon bond. Furthermore, most of the
qualitative results in the paper are shown to be independent of the means
used to finance the debt issue (Theorem 5). Finally, it is concluded that the
relative risk associated with different bonds issued by the same firm cannot
be determined by the structure of priority rules alone. It is also necessary to
consider the timing of the promised payments compared to that of the other
debt issues in the firms capital structure.
These results are consistent with recent empirical studies on bond risk.
Weinstein (1981) shows that risk, measured by a bonds beta, is positively
related to the time to maturity and negatively related to the coupon rate.
These results can be explained by Theorems 1, 2, and 3 relating bond risk to
maturity and the promised payment schedule. However, the relationship
between bond risk and the timing of the promised payments depends
crucially on whether a given leverage ratio is defined by its market value or
book value. This suggests that empirical investigators should pay special
attention to the specification of the leverage ratio as an explanatory variable.
Appendix A
D 1 N&o&) N(-2)
07 j+-CLJ)-f(Z-cT&) =ZY-
(A.1)
x=2--c7 vf 7, y= -2.
W) = 43(Y) 04.2)
where
N(X) 1 -
6_(X)=fo and +(X)= 0 g --
V f(X) 4(x)*
The graphs of $ and 6 are given in fig. 5. Referring to the figure, let AB be
unction Values
Fig 5 A geometric proof showing that the bond elasttclty approaches one as time to maturity
goes to mkuty. The function q(x) is given by &c)=N(x)/f(x) where N(x) is the cumulative
normal density function and f(x) ts the normal density function. The function t&x) 1s given by
I&X)=(D/V)(l/f(x))- d(x), where (D/V) is the leverage ratio. Smce the parameters z and ~4 are
related by (l/(z - gJ) =6(-z), it follows from the figure that when z = AO, then (Z-O&) = OB
In particular, when z tends to mfimty, (Z-CT&) tends to x,0.
402 TS Y Ho and RF Smgev, Bond mdentures and nsk
any horizontal line. Then eq. (A.2) requires z and z be related by points A
and I?. That is,
D
or N(x,)=/.
Appendix B
Let
Proof. N(z-a)N( -z)+O as a-+oo follows from the definition of N(x). For
the second term,
Osyf(x)N(x-a)dxi q f(x)N(x-a)dx.
z -cc
hm 7 f(x)f(x - a) dx = 0.
a+m Z
yj(x)N(x-a)dx-lv(z-n)rj(-z) as z-+-co.
Furthermore,
~f(x)f(x-a)dx=(e-~4/,,/!%) g/($x->)dx.
Proposition B.5. For a given z, there 1s only one value a*, such that
JFCB
404 TS Y Ho and RF Smger, Bond indentures and ruk
where v(x)=f(x)/N(-x) and v-(x) is Mills ratio. It has the property that
O<v < 1 and for large value of x, v(x)=x [Kendall and Stuart (1977)].
Therefore, either (i) &$/aa#O for any value of a or (ii) there exists a unique
value a, such that (&#/&)(a, a,) =O. However the first case contradicts
Propositions 1 and 2. Q.E.D.
Appendix C
where
fs=W), (C.4)
and finally,
From (C.5),
O=d&N(-z)-yf(x)N(y-afi)dxd&+rf(x)N(-y)dxdf,. (C.7)
z
dfi.
J f (W(-y)dx
dy=
fLa$F+ 1f(x)N(y'-afi)dx-N(-zz') (v(x)-~afi
TS Y Ho and R F. Singer, Bond mdentures and rusk 405
1fGW( - Y)dx
+
@x)IV(+c~fi)dx-IV-z)
1
x7
z
f(x-aJT)f(~'--o)l(v(x)-fs)d~. (C.9)
Note that
Furthermore, defining
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