Sears Holdings Corp (SHLD) Enters Into Loan Agreement with ESL Partners, Cascade Investments

UNITED STATES

SECURITIES AND EXCHANGE COMMISSION

Washington, D.C. 20549

SCHEDULE 13D

Under the Securities Exchange Act of 1934

(Amendment No. 45) *

Sears
Holdings Corporation

(Name of Issuer)

Common Shares

(Title of
Class of Securities)

812350106

(CUSIP Number)

Janice V.
Sharry, Esq.

Haynes and Boone, LLP

2323 Victory Avenue, Suite 700

Dallas, Texas 75219

(214) 651-5000

(Name,
Address and Telephone Number of Person Authorized to Receive Notices and Communications)

April 8, 2016

(Date of Event which Requires Filing of this Statement)

If the filing person has
previously filed a statement on Schedule 13G to report the acquisition that is the subject of this Schedule 13D, and is filing this schedule because of §§240.13d-1(e), 240.13d-1(f) or 240.13d-1(g), check the following box. ¨

Note: Schedules filed in paper format shall include a signed original and five copies of the schedule, including all exhibits. See §240.13d-7 for
other parties to whom copies are to be sent.

The information required on the remainder of this cover page shall not be
deemed to be filed for the purpose of Section 18 of the Securities Exchange Act of 1934, as amended (Act) or otherwise subject to the liabilities of that section of the Act but shall be subject to all other provisions of
the Act (however, see the Notes).

This Amendment No. 45 to Schedule 13D (this Amendment) relates to common shares,
par value $0.01 per share (the Holdings Common Stock), of Sears Holdings Corporation, a Delaware corporation (Holdings). This Amendment amends the Schedule 13D, as previously amended, filed with the Securities and Exchange
Commission by ESL Partners, L.P., a Delaware limited partnership (Partners), SPE I Partners, LP, a Delaware limited partnership (SPE I), SPE Master I, LP, a Delaware limited partnership (SPE Master I), RBS
Partners, L.P., a Delaware limited partnership (RBS), ESL Institutional Partners, L.P., a Delaware limited partnership, RBS Investment Management, L.L.C., a Delaware limited liability company, CRK Partners, LLC, a Delaware limited
liability company, ESL Investments, Inc., a Delaware corporation (ESL), and Edward S. Lampert, a United States citizen, by furnishing the information set forth below. Except as otherwise specified in this Amendment, all previous Items
are unchanged. Capitalized terms used herein which are not defined herein have the meanings given to them in the Schedule 13D, as previously amended, filed with the Securities and Exchange Commission (SEC).

Item 2. Identity and Background.

Item 2(a) is hereby amended and restated in its entirety as follows:

(a) This Schedule 13D is being filed by Partners, SPE I, SPE Master I, RBS, ESL and Edward S. Lampert, by furnishing the information set
forth below. Partners, SPE I, SPE Master I, RBS, ESL and Mr. Lampert are collectively defined as the Reporting Persons.

Attached as Annex A hereto and incorporated herein by reference is a list containing the (a) name, (b) citizenship, (c) present
principal occupation or employment and (d) the name, principal business address of any corporation or other organization in which such employment is conducted, of each director and executive officer of ESL (the ESL Director and
Officers). Other than the ESL Director and Officers, there are no persons or corporations controlling or ultimately in control of ESL.

Item 3. Source and Amount of Funds or Other Consideration.

Item 3 is hereby amended and supplemented as follows:

In grants of shares of Holdings Common Stock by Holdings on February 29, 2016 and March 31, 2016, pursuant to the Extension
Letter between Holdings and Mr. Lampert, Mr. Lampert acquired an additional 44,247 shares of Holdings Common Stock. Mr. Lampert received the shares of Holdings Common Stock as consideration for serving as Chief Executive Officer and
no cash consideration was paid by Mr. Lampert in connection with the receipt of such shares of Holdings Common Stock.

In various
open market purchases between February 10, 2016 and April 11, 2016, Mr. Lampert acquired an aggregate of 304,101 shares of Holdings Common Stock for aggregate consideration of approximately $4,536,363 (excluding commissions) using
personal funds.

Item 4. Purpose of Transaction.

Item 4 is hereby amended and supplemented as follows:

On April 8, 2016, Holdings, through Sears, Roebuck and Co., Sears Development Co., Innovel Solutions, Inc., Big Beaver of Florida
Development, LLC and Kmart Corporation (collectively, the Borrowers), entities wholly-owned and controlled, directly or indirectly by Holdings, obtained a $500 million secured short-term loan facility (the Secured Loan
Facility) from JPP, LLC and JPP II, LLC, affiliates of the Reporting Persons (together, the ESL Lenders), and Cascade Investment, L.L.C. (Cascade, and together with the ESL Lenders, the Initial Lenders).
$250 million was funded under the Secured Loan Facility on April 8, 2016, and, subject to the satisfaction of certain conditions, up to an additional $250 million may be drawn by the Borrowers prior to July 7, 2017, the maturity date of
the Secured Loan Facility.

The Secured Loan Facility has an annual base interest rate of 8%, with accrued interest payable monthly during
the term of the Secured Loan Facility. The Borrowers paid an upfront commitment fee to the Initial Lenders equal to 1.0% of the full principal amount of the Secured Loan Facility and also are required to pay a funding fee to the Initial Lenders and
any subsequent lender who provides a portion of the Secured Loan Facility as part of the syndication, including their respective successors and/or assigns (collectively, the Lenders), equal to 1.0% of the

amounts drawn under the Secured Loan Facility at the time such amounts are drawn. If amounts remain outstanding or committed under the Secured Loan Facility after 9 months, a delayed origination
fee equal to 0.5% of such amounts becomes payable, and if amounts remain outstanding or committed under the Secured Loan Facility after 12 months, an additional delayed origination fee equal to 0.5% of such amounts becomes payable.

The Secured Loan Facility is guaranteed by Holdings, is currently secured by a first priority lien on 13 real properties owned by the
Borrowers, and will be secured by an additional 8 real properties beginning on the date any additional amounts are drawn. In certain circumstances, the Lenders may exercise the right to require the Borrowers to replace one or more of the mortgaged
properties with substitute properties. The Secured Loan Facility includes customary representations and warranties, indemnities and covenants, including with respect to the condition and maintenance of the real property collateral.

The Secured Loan Facility has customary events of default, including (subject to certain materiality thresholds and grace periods) payment
default, failure to comply with covenants, material inaccuracy of representation or warranty, and bankruptcy or insolvency proceedings. If there is an event of default, the Lenders may declare all or any portion of the outstanding indebtedness to be
immediately due and payable, exercise any rights they might have under any of the Secured Loan Facility documents (including against the collateral), and require the Borrowers to pay a default interest rate equal to the greater of (i) 2.5% in
excess of the base interest rate and (ii) the prime rate plus 1%. The Secured Loan Facility may be prepaid at any time in whole or in part, without penalty or premium.

Under the terms of the Secured Loan Facility, Holdings is required to retain a broker and use commercially reasonable efforts to syndicate the
Secured Loan Facility. Any subsequent Lender who provides a portion of the Secured Loan Facility as part of the syndication will be entitled to share (based on loan amount and time outstanding) in the origination and funding fees. The ESL Lenders,
on the one hand, and Cascade, on the other, each provided $125 million of the initial $250 million drawn under the Secured Loan Facility and have each committed to provide any portion of the Secured Loan Facility that is not syndicated to other
Lenders.

The foregoing is qualified in its entirety by references to that certain Loan Agreement, entered into in connection with the
Secured Loan Facility, attached hereto as Exhibit 99.26 and incorporated by reference herein.

In connection with the Secured Loan
Facility, on April 8, 2016, the Lenders entered into a co-lender agreement to govern the relationship among the Lenders with respect to their interests in the Secured Loan Facility (the Co-Lender Agreement). Pursuant to the
Co-Lender Agreement, the ESL Lenders were named as administrative agent and collateral agent for themselves and the other Lenders for purposes of administration of the Secured Loan Facility and, in connection therewith, the ESL Lenders may take any
and all actions on behalf of the Lenders as the Lenders are obligated or entitled to take under the terms of the Co-Lender Agreement, the Secured Loan Facility and/or other documents entered into in connection therewith, subject to certain actions
that require the consent of some or all of the other Lenders. In addition, the Co-Lender Agreement governs (i) the process for the distribution of any origination fees, funding fees, delayed origination fees, and/or other funds in connection
with the Secured Loan Facility, (ii) the ability of Cascade to transfer its interest in the Secured Loan Facility to an additional Lender, and (iii) the voting and approval process for actions to be taken by or on behalf of the Lenders
with respect to the Secured Loan Facility.

The foregoing is qualified in its entirety by references to the Co-Lender Agreement attached
hereto as Exhibit 99.27 and incorporated by reference herein.

Also on April 8, 2016, Holdings, Sears Roebuck Acceptance Corp. and
Kmart Corporation closed on a $750 million Senior Secured Term Loan (the Term Loan). Certain affiliates of the Reporting Persons have advised Holdings and Bank of America, N.A., as agent for the Term Loan, that they intend to participate
in the syndicate of lenders with respect to the Term Loan for $150 million of the Term Loan. The syndication has not yet been finalized.

Item 5. Interest in Securities of the Issuer.

Item 5 is hereby amended and restated in its entirety as follows:

(a)-(b) Each Reporting Person declares that neither the filing of this statement nor
anything herein shall be construed as an admission that such person is, for the purposes of Section 13(d) or 13(g) of the Act or any other purpose, the beneficial owner of any securities covered by this statement.

Each Reporting Person may be deemed to be a member of a group with respect to Holdings or securities of Holdings for the purposes of
Section 13(d) or 13(g) of the Act. Each Reporting Person declares that neither the filing of this statement nor anything herein shall be construed as an admission that such person is, for the purposes of Section 13(d) or 13(g) of the Act
or any other purpose, (i) acting (or has agreed or is agreeing to act) with any other person as a partnership, limited partnership, syndicate, or other group for the purpose of acquiring, holding, or disposing of securities of Holdings or
otherwise with respect to Holdings or any securities of Holdings or (ii) a member of any syndicate or group with respect to Holdings or any securities of Holdings.

As of the time of filing on April 12, 2016, the Reporting Persons may be deemed to beneficially own the shares of Holdings Common Stock
set forth in the table below.

(c) Other than as set forth on Annex B hereto, there have been no transactions in the class of securities reported on that were effected by
the Reporting Persons during the past sixty days or since the most recent filing of Schedule 13D, whichever is less.

Item 6. Contracts, Arrangements, Understandings or Relationships With Respect
to Securities of the Issuer.

Item 6 is hereby amended and supplemented as follows:

The information set forth in Item 4 is incorporated by reference into this Item 6.

Item 7. Material to be Filed as Exhibits.

Item 7 is hereby amended and restated in its entirety as follows:

The following exhibits are filed as exhibits hereto:

SIGNATURE

After reasonable inquiry and to the best of my knowledge and belief, I certify that the information set forth in this statement is true,
complete and correct.

ANNEX A

The names, business addresses, present principal occupations, and citizenship of the directors and executive officers of ESL Investments,
Inc. are set forth below. The directors or executive officers principal business address is 1170 Kane Concourse, Suite 200, Bay Harbor, Florida 33154. Each occupation set forth opposite an individuals name refers to ESL
Investments, Inc.

ANNEX B

RECENT TRANSACTIONS BY THE REPORTING PERSONS IN THE SECURITIES OF

SEARS HOLDINGS CORPORATION

EXHIBIT INDEX