Exhibit 10.1

SEPARATION AGREEMENT AND GENERAL RELEASE

This Separation Agreement and General Release (“Agreement”) is entered into by
William C. Long (“Employee”) and Diamond Offshore Management Company and its
parent, subsidiaries and affiliated companies (collectively the “Company”).

WHEREAS, Employee and Company entered into that certain Employment Agreement
dated December 15, 2006 (the “Employment Agreement”); and

WHEREAS, in recognition of Employee’s service to the Company, Employee and
Company mutually agree to Employee’s voluntary separation with the Company to be
effective on June 11, 2014;

NOW, THEREFORE, for and in consideration of the mutual promises, covenants and
obligations contained herein, Employee and Company agree as follows:

1. Separation of Employment. Employee shall resign his employment as Senior Vice
President, General Counsel & Secretary with Company at the close of business on
June 11, 2014 (the “Separation Date”). Prior to the Separation Date, Employee
shall only be required to perform duties as specifically requested by the
President of the Company or his designee. Company and Employee agree that
Company records and announcements shall describe Employee’s separation as a
voluntary resignation.

2. Separation Benefits. Subject to any applicable requirements of Section 17
below, the Company shall pay or provide the Separation Benefits as follows:

 

  (a) Commencing on the Company’s first payroll period following the later of
the Separation Date or Effective Date, and continuing on subsequent
regularly-scheduled payroll periods, but no less frequently than on a monthly
basis, the Company will pay Employee twenty-four (24) months of his current base
salary (for a total of $899,416.08), less withholdings and deductions in
accordance with applicable law.

 

  (b)

After the Separation Date, Employee’s eligibility for continuation of coverage
under the Company’s group medical, dental and vision insurance plans normally
would be governed exclusively by the continuation coverage provisions of such
plans and the Consolidated Omnibus Budget Reconciliation Act of 1985 (“COBRA”).
Pursuant to this Agreement, however, during any portion of the period beginning
on the first day of the month immediately following the Separation Date and
ending two (2) years later that Employee and his spouse/family participate in a
Company group medical, dental or vision insurance plan through COBRA, the full
COBRA premium for such medical, dental and vision insurance coverage for
Employee and his spouse/family dependents will be paid by Company promptly to
insure that such insurance coverage continues without interruption or lapse of
coverage; provided, however, that if the continued medical, dental and vision
benefits are discriminatory so that such benefit would be taxable to Employee
then the premium will be paid by Employee on an after tax basis and the Company
shall reimburse Employee for such payments in each following month so that such
benefits will not be taxable to the Employee under Code Section 105(h). The
Company and Employee agree that Employee’s “qualifying event” for the purposes
of

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  COBRA coverage occurs on the Separation Date. In addition, for a period of two
(2) years following the Separation Date the Company will continue to provide
Employee with any Company-paid, or employee elected as of January 1, 2014, life
and disability insurance covering Employee on the date hereof.

 

  (c) The Company will pay Employee a pro rata incentive compensation award for
2014, based upon the same terms and levels as other senior vice-presidents. The
award shall be paid in the normal course at the time the Company pays the 2014
award to its executive officers. The foregoing award shall be made in accordance
with the Diamond Offshore Drilling Inc. Incentive Compensation Plan for
Executive Officers and be subject to the approval of the Compensation Committee
of the Board of Directors.

 

  (d) Upon the Separation Date, all unvested Stock Appreciation Rights (“SARs”)
awarded to Employee shall vest, and all of Employee’s vested stock options and
SARs shall be exercisable by him as provided for in the Second Amended and
Restated Diamond Offshore Drilling, Inc. 2000 Stock Option Plan and the Diamond
Offshore Drilling, Inc. (the “Option Plan”) and the Award Certificates related
thereto.

 

  (e) Any amounts to which Employee is eligible under the Company’s Supplemental
Executive Retirement Plan shall be paid to Employee in accordance with the terms
of that plan.

 

  (f) The Company shall, at its sole expense as incurred, provide Employee with
outplacement services for a period not to exceed twelve (12) months following
the Separation Date and in a total amount not to exceed $25,000. Employee shall
select the outplacement provider, subject to Company approval.

 

  (g) Nothing in this Agreement adversely affects any right Employee may have
to: (i) base wages earned by Employee through the Separation Date, and Employee
shall be paid all such wages regardless of whether Employee signs this
Agreement; (ii) earned, unused vacation, which will be paid by the Company after
the Separation Date; (iii) reimbursement for approved business expenses incurred
by Employee through the Separation Date for which Employee has not been
reimbursed; and (iv) continuation of insurance coverage pursuant to the terms of
Company-provided insurance plans or applicable law. Employee acknowledges that,
except as set forth in this Agreement, the Company does not have, and will not
have, any obligation to provide Employee at any time in the future with any
payments, benefits or considerations other than those recited in Section 2 of
this Agreement. Employee agrees that some of the payments and benefits described
in this Section 2 are not required under the Company’s normal policies and
procedures, and they provide adequate consideration for this Agreement.

3. Full General Release. Employee makes the following promises, commitments and
representations to the Company in consideration for the Company’s execution of
this Agreement and the performance of its terms and conditions:

 

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Employee, on behalf of himself and his spouse, family members, heirs,
successors, and assigns, hereby voluntarily, irrevocably, and unconditionally
releases and forever discharges the Released Parties (defined below),
individually and collectively, from any and all claims, complaints, demands,
liabilities, or causes of action, of whatever kind or character, whether known
or unknown or whether in law or in equity, which he now has or ever had against
any of the Released Parties, in their individual, corporate of official
capacities, including, but not limited to: (i) those claims arising out of or in
any way connected with his employment by the Company and/or the termination of
that employment, (ii) those claims arising prior to the date of this Agreement,
regardless of whether such claims relate to Employee’s employment by the
Company, and (iii) those claims arising out of or in any way connected with any
employment relationship that he now has or ever had with any of the other
Released Parties and/or the termination of any such employment relationship.
Without limiting the generality of the foregoing, the claims being released by
Employee include, but are not limited to, the following: any claim against any
of the Released Parties under the Civil Rights Act of 1866, the Civil Rights Act
of 1871, the Civil Rights Act of 1964, the Civil Rights Act of 1991, the Age
Discrimination in Employment Act, the Americans with Disabilities Act, the
Worker Adjustment and Retraining Notification Act, the Family and Medical Leave
Act, the Employee Retirement Income Security Act, the Fair Labor Standards Act,
the Texas Labor Code, any other federal, state or local statute, regulation,
ordinance, law, or common law relating to employment or employment
discrimination, any alleged violation of any federal, state or local statutes,
ordinances or common laws, tortious or contractual wrongful discharge or
conduct, fraud, negligence, gross negligence, breach of express or implied
contract, vicarious liability for the torts of others. breach of the covenant of
good faith and fair dealing, violation of public policy, tortious interference
with contract or prospective business relations, intentional or negligent
infliction of emotional distress, fraud or misrepresentation, battery or
assault, invasion of privacy, failure to pay wages, stock awards, bonuses,
commissions, incentive pay, benefits, vacation pay, profit sharing, severance or
other compensation of any sort, and harassment, retaliation or discrimination on
the basis of race, color, national original, religion, sex, sexual
preference/orientation, age, handicap or disability.

This Release is not intended to apply to any pension or insured benefits, or any
other equity grant for which Employee is eligible, pursuant to the terms of any
employee benefit plan or Option Plan in which Employee is, or has been, a
participant. The claims released in this Section 3 include any that Employee may
have or assert against the Released Parties in any jurisdiction whatsoever.

By signing this Agreement, it is Employee’s intent to waive and release all
claims and potential claims against the Released Parties, save and except a
claim for unemployment benefits or any other claim that Employee cannot waive or
release as a matter of law. In the unlikely event that a claim or potential
claim (save and except a claim that cannot be waived or released) has been
omitted from this Release, Employee hereby assigns and conveys said claims and
potential claims to the Company in exchange for the Company’s obligations in
this Agreement.

 

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4. No Admission of Wrongdoing. The existence and execution of this Agreement
shall not be considered as an admission of any wrongdoing liability, violation,
error, or omission by Employee or the Company.

5. Knowing and Voluntary Agreement. Employee acknowledges and agrees that:

 

  (a) This Agreement is written in a manner that he understands. Under this
Agreement, Employee is receiving things of value to which he would not otherwise
be entitled to receive.

 

  (b) He has been permitted and offered twenty-one (21) days to consider and to
sign this Agreement and he is hereby advised by the Company to consult with an
attorney prior to executing this Agreement.

 

  (c) Notwithstanding the other provisions of this Agreement, Employee is not
releasing or waiving in this Agreement any claims under the Age Discrimination
in Employment Act that may arise after the date he signs this Agreement.

 

  (d) He has received the opportunity to review and reflect on all terms of this
Agreement, and has not been subject to any undue or improper influence
interfering with the exercise of his free will to execute this Agreement. He
knowingly and voluntarily agrees to all of the terms set forth in this
Agreement, and knowingly and voluntarily intends to be legally bound by them.

6. Effective Date. Employee has seven (7) days following his execution of this
Agreement to revoke this Agreement. This Agreement will not become effective or
enforceable until the seven (7) day revocation period has expired. In the event
that Employee exercises the right to revoke this Agreement, neither the Company
nor Employee will have any obligations under this Agreement. If Employee chooses
to revoke this Agreement, he must do so in writing addressed and delivered by
email to Lynn Charles at lcharles@dodi.com and by certified mail, return receipt
requested to him at the Company’s corporate address in Houston, Texas.

7. “Released Parties.” As used in this Agreement, the term “Released Parties”
means Diamond Offshore Management Company, Diamond Offshore Drilling, Inc. and
its/their past and present parent, subsidiary and affiliate companies and its
and their respective: (i) predecessors and successors; and (ii) past and present
employees, owners, partners, shareholders, members, directors, officers,
attorneys, assigns, agents, and representatives, both individually and in their
official capacities.

8. Return of Property. Employee represents that on or before the Separation
Date, he shall return all Company property and documents, including copies of
any documents, in his possession or control, including without limitation any
building keys, laptop computer, personal digital assistant, telephone calling
card(s), credit card(s), forms, files, manuals, correspondence, memoranda,
notes, e-mail, plans, business records, reports, financial data or records,
personnel data, contracts, contract information, training materials, product mix
or recipes, lists of employees, salary and benefits information (except relating
to Employee), lists of suppliers and vendors, brochures, catalogs, computer
tapes and diskettes or other portable media, computer-readable files and data
stored on any hard drive anywhere or other

 

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installed or portable device, passwords, data processing reports, reports or
recordings in any electronic or physical format, and any and all other documents
or property which Employee has obtained by virtue of his employment with the
Company. Notwithstanding the foregoing, the Company agrees that Employee shall
be entitled to: (1) keep his cell phone and current cell phone number, and the
Company will take all steps necessary to effect the transfer to Employee’s
personal cell phone account; and (2) retain publicly available documents and
data, clothing, caps, hunting gear, personal mementos (including but not limited
to plaques, rig photographs, deal toys, and corporate giveaways now in his
possession), and a list of the mailing addresses of the Company’s employees (to
be used for holiday cards and other personal contact). Employee will take
reasonable steps to return all paper files and delete all electronic files
containing non-public Company documents, but the Company acknowledges that,
given Employee’s tenure with the Company, Employee might later discover
documents or data at his residence and/or on his personal computer(s), which he
agrees not to use for any purpose and to immediately destroy or delete.

9. Nondisparagement.

 

  (a) Employee agrees that he will not make or cause to be made any oral or
written statements that are derogatory, defamatory, disparaging or harmful
concerning the Company, its policies or programs, or its past or present
officers, directors, employees, agents, or business associates, including but
not limited to its past or present suppliers or vendors, or take any actions
that are harmful to the business affairs of the Company and/or its employees.
Employee further agrees that he will not make or cause to be made any oral or
written statements regarding the Company’s Confidential Information to any third
party, including, but not limited to, the general public (for example, via
postings or publications on the internet), the media, financial analysts,
auditors, institutional investors, consultants, suppliers, vendors, or business
associates, or agents and/or representatives of any of the foregoing, unless
such statement is: (i) expressly authorized by the Company in writing, or
(ii) required by law. This provision is a material and substantial term of this
Agreement.

 

  (b) Company’s Board of Directors, President and Senior Vice-Presidents agree
they will not make or cause to be made any oral or written statements about
Employee that are derogatory, defamatory, or disparaging about Employee unless
required by law.

 

  (c) Employee shall direct any third parties seeking an employment reference
for Employee to the Company’s Vice President – Human Resources, who shall only
provide Employee’s dates of employment and position held and the information
contained in any internal or public release, unless Employee agrees and directs
in writing that the Company can furnish additional information.

10. Cooperation/Transition.

 

  (a)

Employee agrees to reasonably cooperate with the Company, and any of the other
Released Parties in any matter related to the Company’s business or activities,
as follows: (i) to be available at mutually agreeable times, personally or by
telephone, as necessary, at such reasonable times and without unreasonable
interference with Employee’s employment or personal activities, to provide such
information and services as may be

 

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  from time to time requested by the Company in connection with various matters
in which Employee was involved during his employment with the Company or matters
about which Employee has knowledge and expertise; and (ii) in all pending and
future litigation (including claims asserted with administrative agencies)
involving the Company or any of the other Released Parties, which obligation
includes Employee promptly meeting with counsel for the Company or the other
Released Parties at mutually agreeable and reasonable times upon their request
and providing testimony in court or upon deposition that is truthful, accurate,
and complete, according to information known to Employee. Employee further
agrees to reasonably cooperate with the Company in connection with any
investigation or review by any federal, state or local regulatory authority
relating to events or occurrences that transpired while Employee was employed
with the Company.

 

  (b) If Employee receives a subpoena seeking testimony, documents or
information Employee may have related to the Company or any of its affiliates,
Employee or Employee’s attorney shall provide the Company with a copy of the
subpoena prior to the date specified for compliance and no later than four
(4) business days following Employee’s receipt of it. In addition, as soon as
possible prior to the date of compliance required by such a subpoena, Employee
shall notify the Company of the content of any information to be provided
pursuant to such a subpoena and give the Company copies of all documents to be
produced.

 

  (c) The Company shall reimburse Employee, upon receipt of proper
documentation, for all reasonable and necessary expenses for air fare,
accommodations, transportation, meals and other out-of-pocket expenses incurred
by Employee in providing the cooperation requested of him pursuant to this
Section 10.

11. Confidential Information. Employee agrees that, unless otherwise required by
law, Employee will forever keep secret and inviolate all Confidential
Information which has come into Employee’s possession, and Employee will not use
the same for Employee’s own private benefit, or directly or indirectly for the
benefit of others, and Employee will not disclose such Confidential Information
to any other person. If Employee is legally compelled (by deposition,
interrogatory, request for documents, subpoena, civil investigative demand or
similar process) to disclose any Confidential Information, Employee shall
provide the Company with prompt prior written notice of such legal requirement
so that the Company may seek a protective order or other appropriate remedy
and/or waive compliance with the terms of this Section 11. In any event,
Employee may furnish only that portion of the Confidential Information which
Employee is advised by legal counsel is required, and Employee shall exercise
Employee’s best efforts to obtain an order or assurance that confidential
treatment will be accorded such Confidential Information that is disclosed. For
purposes of this Agreement, all confidential or proprietary information
concerning the business and affairs of the Company, including without
limitation, all trade secrets, knowhow and other information generally retained
on a confidential basis by the Company concerning its products, methods,
know-how, techniques, systems, software codes and specifications, formulae,
inventions and discoveries, business plans, pricing, product plans and the
identities of and the nature of the Company’s dealings with its employees,
suppliers and customers, whether or not such information shall, in whole or in
part, be subject to or capable of being protected by patent, copyright or
trademark laws, shall constitute “Confidential Information.” Notwithstanding
anything contained herein which may be to the contrary, the term “Confidential
Information” does not include any information which is excepted as confidential
information in Article 4.6 of the Employment Agreement.

 

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12. Agreement not to Solicit Employees/Former Employees. Employee acknowledges
and re-affirms his agreement in Article 4.7 of his Employment Agreement that for
a period of two (2) years after his Separation Date, Employee shall not,
directly or knowingly indirectly, either as an executive, employer, independent
contractor, consultant, agent, principal, partner, stockholder, officer,
director, or in any other individual or representative capacity, either for his
own benefit or the benefit of any other person or entity: (a) solicit, recruit,
induce, entice, encourage or in any way cause any officer, or manager reporting
to such officer, holding such position at the time Employee ceases to be an
employee of Company and who is or was an employee of Company (or affiliate)
within the six (6) months prior to Employee’s termination of employment with
Company or thereafter to terminate his/her employment with Company (or such
affiliate); or (b) directly solicit for hire, directly entice for hire, hire, or
directly recruit any officer, or manager reporting to such officer, toolpusher,
rig superintendent or offshore installation manager (OIM) holding such position
at the time Employee ceases to be an employee of Company and who is or was an
employee of Company within the six (6) months prior to Employee’s separation of
employment with Company or thereafter.

13. Breach Causing Irreparable Harm. The terms of this Agreement are contractual
and not merely recitals. Employee agrees that a breach by Employee of Sections
11 and 12 of this Agreement will result in irreparable harm to the Company, and
as such, upon such breach, without limiting the Company’s right to seek
injunctive relief allowed by law in a court of competent jurisdiction, the
Company may pursue a claim against Employee for any damages suffered by Company
as a result of such breach. Employee’s agreements in Section 12 shall be
extended for the period of time which Employee violates one or more of these
agreements and/or during any period during which the Company appeals from an
order refusing to enforce any of these agreements or covenants. The tolling or
extension period shall not exceed twelve (12) months under any circumstances.

14. Reliance; Complete Agreement; Modification. Employee and the Company
acknowledge that in executing this Agreement they have not relied on any
statements, promises or representations made by the other party except as
specifically memorialized in this Agreement. This Agreement constitutes the
complete agreement of the parties on or in any way related to the subject matter
addressed herein. The parties further agree that this Agreement supersedes the
Employment Agreement unless otherwise stated herein. Additionally, Article 5.11
of the Employment Agreement is incorporated by reference into this Agreement
only insofar as it prohibits employee from seeking employment with the Company
in the future. This Agreement cannot be modified or rescinded except upon the
written consent of both Employee and the Company.

15. Severability. If any provision of this Agreement is held to be
unenforceable, such provision shall be considered to be distinct and severable
from the other provisions of this Agreement, and such unenforceability shall not
affect the validity and enforceability of the remaining provisions. If any
provision of this Agreement is held to be unenforceable as written but may be
made enforceable by limitation, then such provision shall be enforceable to the
maximum extent permitted by applicable law. No failure by either party hereto at
any time to give notice of any breach by the other party of, or to require
compliance with, any condition or provision of this Agreement shall be deemed a
waiver of similar or dissimilar provisions or conditions at the same or at any
prior or subsequent time.

 

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16. Governing Law; Venue; Jury Waiver. The Company and Employee agree that the
law of Texas without regard to conflicts of law principles shall exclusively
govern any disputes between the parties, including but not limited to, the
validity, interpretation, and effect of this Agreement, as well as any other
disputes arising out of or relating to the employment of Employee by the
Company. In the event of any dispute between them, including, but not limited to
any disputes arising out of this Agreement, Employee’s employment with the
Company and work for the Company, the parties agree to exclusive, mandatory and
sole jurisdiction and venue in Houston, Texas. The parties agree and consent to
have all such disputes resolved by a judge in the courts of Harris County,
Texas. The Company and Employee hereby consent to the exclusive jurisdiction and
venue there. The Parties hereby waive all challenges to personal jurisdiction
and venue of such courts, including, but not limited to, the claim or defense
that such courts or locale constitute an inconvenient forum. The parties agree
that any disputes between them shall be adjudicated by a judge and, therefore,
the parties waive a trial by jury.

17. Code Section 409A.

 

  (a) Deferred Compensation. To the extent any payments or benefits under this
Agreement constitute deferred compensation subject to Code Section 409A of the
Internal Revenue Code of 1986, as amended (the “Code”), and the regulations
thereunder (collectively “Section 409A”) this Agreement shall be administered,
interpreted and construed to comply with the requirements of Code Section 409A.
The portion of any payment or benefit under this Agreement that is paid within
the short-term deferral period or is otherwise exempt from Code Section 409A
will not be treated as nonqualified deferred compensation and will not be
aggregated with other nonqualified deferred compensation plans or payments to
the extent permitted under Code Section 409A.

 

  (b) Separate Payments and Payment Timing. Payment dates provided for in this
Agreement will be deemed to incorporate grace periods that are treated as made
upon a designated payment date within the meaning of Code Section 409A and
Treas. Regs. §1.409A-3(d).

 

  (c) General Section 409A Provisions. If Employee or the Company determines
that any payments or benefits payable under this Agreement intended to comply
with Code Section 409A and do not comply with Section 409A of the Code, Employee
and the Company agree to amend this Agreement, or take such other actions as
Employee and the Company deem reasonably necessary or appropriate, to comply
with the requirements of Section 409A of the Code (and any applicable relief
provisions), while preserving the economic agreement of the parties. If any
provision of the Agreement would cause such payments or benefits to fail to so
comply, such provision will not be effective and will be null and void with
respect to such payments or benefits, and such provision will otherwise remain
in full force and effect.

All payments considered nonqualified deferred compensation under Section 409A
and the regulations thereunder will be made on the date(s) provided herein and
no request to accelerate or defer any payment under this Section will be
considered or approved for any reason whatsoever, except as permitted under
Section 409A. Notwithstanding the foregoing, amounts payable hereunder which are
not nonqualified deferred compensation, or which may be accelerated pursuant to
Section 409A, such as distributions for applicable tax payments, may be
accelerated, but not deferred, at the sole discretion of Company.

 

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To the extent required to comply with Section 409A, all references in this
Agreement to termination of employment or termination mean Employee’s
“separation from service” as that term is defined in Section 1.409A-1(h) of the
Treasury Regulations.

 

  (d) Reimbursements and In-Kind Benefits. If any coverage (whether provided
before or after Employee’s termination of employment) under medical, dental,
disability and/or life insurance plan, or the provision of any other benefit or
perquisite, results in in-kind benefits or reimbursements to Employee that are
(x) taxable for federal income tax purposes and (y) deferred compensation
subject to Section 409A, then such in-kind benefits or reimbursements shall be
subject to the following rules:

 

  (i) The in-kind benefits to be provided, or the amounts to be reimbursed,
shall be determined pursuant to the terms of the applicable benefit plan, and
shall be limited, in addition to any other applicable limitations, to Employee’s
lifetime and the lifetime of Employee’s eligible dependents.

 

  (ii) The amounts eligible for reimbursement, or the in-kind benefits provided,
during any calendar year may not affect the expenses eligible for reimbursement,
or the in-kind benefits provided, in any other calendar year.

 

  (iii) Any reimbursement of an eligible expense shall be made on or before the
last day of the calendar year following the calendar year in which the expense
was incurred.

 

  (iv) Employee’s right to an in-kind benefit or reimbursement is not subject to
liquidation or exchange for cash or another benefit.

 

  (e) Specified Employee Status. If Employee is a specified employee (within the
meaning of Code Section 409A) on the date of his separation from service, any
payments made with respect to such separation from service under this Agreement,
and other payments or benefits under this Agreement that are subject to
Section 409A of the Code, will be delayed in order to comply with
Section 409A(a)(2)(B)(i) of the Code, and such delayed payments or benefits will
be paid in a lump sum upon expiration of such six (6) month period with all
accrued interest calculated from the Date of Termination until such lump sum
payment and equal to the average six (6) month U.S. Treasury Rate for the year
six-month period measured from the date of Employee’s separation from service.
Any remaining payments and benefits due under the Agreement will be paid as
otherwise provided in the Agreement

 

  (f) Amounts Subject to Release. To the extent any amounts payable hereunder is
considered nonqualified deferred compensation subject to Section 409A and the
period during which Employee has discretion to execute or revoke a release
straddles two taxable years of Employee, then the Company will commence the
payments and/or benefits in the second of such taxable years, and Employee may
not, directly or indirectly, designate the calendar year of any such payment.

 

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Each of the undersigned acknowledges that he/it (a) has read and fully
understands all the terms and conditions of this Agreement, (b) has had
sufficient time to consider this Agreement and to consult about it with an
attorney, and (c) is signing it knowingly, voluntarily and willingly. This
Agreement is effective once signed by all the parties and can be executed in
multiple identical counterparts and via email and fax.

IN WITNESS WHEREOF, the parties have executed this Agreement on the date
specified below.

 

Date: 11 June 2014    

\s\ William C. Long

   

William C. Long

Employee

    DIAMOND OFFSHORE MANAGEMENT COMPANY    

\s\ Robert L. Charles

    Name:     Title:

 

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