Document:

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                                                                    EXHIBIT 4.53

                             SUPPLEMENTAL INDENTURE

         Supplemental Indenture (this "Supplemental Indenture"), dated as of
December 1, 1999, among Empress Casino Hammond Corporation, Hammond Residential,
L.L.C. and Empress Casino Joliet Corporation (collectively, the "Subsidiary
Guarantors"), each a Subsidiary of Horseshoe Gaming Holding Corp., a Delaware
corporation (the "Company"), the successor to Horseshoe Gaming, L.L.C. ("LLC")
under the Indenture, dated as of June 15, 1997 (the "Indenture"), among LLC,
Robinson Property Group, Limited Partnership and U.S. Trust Company of Texas,
N.A., as trustee (the "Trustee"), providing for the issuance of 9_% Senior
Subordinated Notes due 2007 (the "Notes").

                               W I T N E S S E T H

         WHEREAS, the Company has heretofore executed and delivered to the
Trustee a Supplemental Indenture, dated as of December 1, 1999, under which the
Company assumed all of LLC's obligations under the Indenture and the Notes;

         WHEREAS, the Indenture provides that under certain circumstances the
Subsidiaries of the Company are required to execute and deliver to the Trustee a
supplemental indenture pursuant to which such Subsidiaries shall unconditionally
guarantee all of the Company's obligations under the Notes and the Indenture on
the terms and conditions set forth herein (the "Subsidiary Guarantee").

         NOW, THEREFORE, in consideration of the foregoing and for other good
and valuable consideration, the receipt of which is hereby acknowledged, the
Subsidiary Guarantors, the Company and the Trustee mutually covenant and agree
for the equal and ratable benefit of the Holders of the Notes as follows:

         1. Capitalized Terms. Capitalized terms used herein without definition
shall have the meanings assigned to them in the Indenture.

         2. Agreement to Guarantee. The Subsidiary Guarantors jointly and
severally irrevocably and unconditionally guarantee to each Holder of a Note
authenticated and delivered by the Trustee and its successors and assigns,
irrespective of the validity or enforceability of the Indenture, the Notes or
the Obligations of the Company under the Indenture or the Notes, that (x) the
principal and premium (if any) of and interest and Liquidated Damages, if any,
on the Notes and related costs and expenses will be paid in full when due,
whether at the maturity or interest payment date, by acceleration, call for
redemption, upon an Offer to Purchase, or otherwise and interest on the overdue
principal and premium (if any) of and interest and Liquidated Damages, if

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any, on the Notes and all other obligations of the Company to the Holders or the
Trustee under the Indenture or the Notes will be promptly paid in full or
performed all in accordance with the terms of the Indenture and the Notes; and
(y) in case of any extension of time of payment or renewal of any Notes or any
of such other obligations, they will be paid in full when due in accordance with
the terms of the extension or renewal, whether at maturity, by acceleration,
call for redemption, upon an Offer to Purchase or otherwise.

         The obligations of the Subsidiary Guarantors to the Holders and to the
Trustee pursuant to this Supplemental Indenture and the Indenture are expressly
set forth in Article XII of the Indenture and reference is hereby made to such
Indenture for the precise terms of this Supplemental Indenture.

         THE TERMS OF ARTICLE XII OF THE INDENTURE ARE INCORPORATED HEREIN BY
REFERENCE.

         No past, present or future director, officer, employee, incorporator or
stockholder (direct or indirect) of the Guarantors (or any such successor
entity), as such, shall have any liability for any Obligations of the Guarantors
under this Supplemental Indenture or the Indenture or for any claim based on, in
respect of, or by reason of, such Obligations or their creation, except in their
capacity as an obligor or Guarantor of the Notes in accordance with the
Indenture.

         This is a continuing Guarantee and shall remain in full force and
effect and shall be binding upon the Subsidiary Guarantors and their successors
and assigns until full and final payment of all of the Obligations under the
Notes and Indenture or until released in accordance with the Indenture and shall
inure to the benefit of the successors and assigns of the Trustee and the
Holders, and, in the event of any transfer or assignment of rights by any Holder
or the Trustee, the rights and privileges herein conferred upon that party shall
automatically extend to and be vested in such transferee or assignee, all
subject to the terms and conditions hereof. This is a guarantee of payment and
not of collectibility.

         The Obligations of the Subsidiary Guarantors under this Supplemental
Indenture shall be limited to the extent necessary to ensure that they do not
constitute a fraudulent conveyance under applicable law.

         3. NEW YORK LAW TO GOVERN. THE INTERNAL LAW OF THE STATE OF NEW YORK
SHALL GOVERN AND BE USED TO CONSTRUE THIS SUPPLEMENTAL INDENTURE, INCLUDING,
WITHOUT LIMITATION, SECTION 5-1401 OF THE NEW YORK GENERAL OBLIGATIONS LAW.

         4. Counterparts. The parties may sign any number of copies of this
Supplemental Indenture. Each signed copy shall be an original, but all of them
together represent the same agreement.

                                      -2-

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         5. Effect of Headings. The Section headings herein are for convenience
only and shall not affect the construction hereof.

         IN WITNESS WHEREOF, the parties hereto have caused this Supplemental
Indenture to be duly executed and attested, all as of the date first above
written.

                             COMPANY:

                             HORSESHOE GAMING HOLDING CORP.

                                      ---------------------------------
                                      Name: Jack B. Binion
                                      Title:   President

                             THE SUBSIDIARY GUARANTORS:

                             EMPRESS CASINO HAMMOND CORPORATION

                             By:
                                 ---------------------------------------
                                      Name: Jack B. Binion
                                      Title:   President

                             EMPRESS CASINO JOLIET CORPORATION

                             By:
                                 --------------------------------------
                                      Name: Jack B. Binion
                                      Title:   President

                             HAMMOND RESIDENTIAL, L.L.C.

                             By:      EMPRESS CASINO HAMMOND
                                      CORPORATION,
                                      its Managing Member

                                      ---------------------------------
                                      Name: Jack B. Binion
                                      Title:   President

                                  THE TRUSTEE:

                                  U.S. TRUST COMPANY OF TEXAS, N.A.

                                  By:
                                      ---------------------------------
                                      Name:
                                      Title:

                                      -3-<PAGE>   1

                                                                    EXHIBIT 4.54

                             SUPPLEMENTAL INDENTURE

         Supplemental Indenture (this "Supplemental Indenture"), dated as of
December 1, 1999, among New Gaming Capital Partnership, Horseshoe Entertainment,
Horseshoe Gaming, L.L.C., Horseshoe GP, Inc., Empress Casino Hammond
Corporation, Empress Casino Joliet Corporation, Hammond Residential, L.L.C.,
Robinson Property Group, Limited Partnership and Bossier City Land Corporation
(collectively, the "Guaranteeing Subsidiaries"), each a Subsidiary of Horseshoe
Gaming Holding Corp., a Delaware corporation (the "Company"), the Company and
U.S. Trust Company, National Association, as trustee under the Indenture
referred to below (the "Trustee").

                               W I T N E S S E T H

         WHEREAS, the Company has heretofore executed and delivered to the
Trustee an indenture (the "Indenture"), dated as of May 11, 1999, providing for
the issuance of 8_% Senior Subordinated Notes due 2009 (the "Notes");

         WHEREAS, the Indenture provides that under certain circumstances the
Subsidiaries of the Company are required to execute and deliver to the Trustee a
supplemental indenture pursuant to which such Subsidiaries shall unconditionally
guarantee all of the Company's obligations under the Notes and the Indenture on
the terms and conditions set forth herein (the "Subsidiary Guarantee"); and

         WHEREAS, pursuant to Section 9.1 of the Indenture, the Trustee is
authorized to execute and deliver this Supplemental Indenture.

         NOW, THEREFORE, in consideration of the foregoing and for other good
and valuable consideration, the receipt of which is hereby acknowledged, the
Guaranteeing Subsidiaries and the Trustee mutually covenant and agree for the
equal and ratable benefit of the Holders of the Notes as follows:

         1. Capitalized Terms. Capitalized terms used herein without definition
shall have the meanings assigned to them in the Indenture.

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         2. Agreement to Guarantee. The Guaranteeing Subsidiaries irrevocably
and unconditionally guarantee the Guarantee Obligations, which include (i) the
due and punctual payment of the principal of, premium, if any, and interest and
Liquidated Damages, if any, on the Notes, whether at maturity, by acceleration,
call for redemption, upon a Change of Control Offer, upon an Asset Sale Offer or
otherwise, the due and punctual payment of interest on the overdue principal and
premium, if any, and (to the extent permitted by law) interest on any interest
on the Notes, and payment of expenses, and the due and punctual performance of
all other obligations of the Company, to the Holders or the Trustee all in
accordance with the terms set forth in Article X of the Indenture, (ii) in case
of any extension of time of payment or renewal of any Notes or any such other
obligations, that the same will be promptly paid in full when due or performed
in accordance with the terms of the extension or renewal, whether at stated
maturity, by acceleration, call for redemption, upon a Change of Control Offer,
upon an Asset Sale Offer or otherwise, and (iii) the payment of any and all
costs and expenses (including reasonable attorneys' fees) incurred by the
Trustee in enforcing any rights under this Supplemental Indenture.

         The obligations of the Guaranteeing Subsidiaries to the Holders and to
the Trustee pursuant to this Supplemental Indenture and the Indenture are
expressly set forth in Article X of the Indenture and reference is hereby made
to such Indenture for the precise terms of this Supplemental Indenture.

         No past, present or future director, officer, employee, incorporator or
stockholder (direct or indirect) of the Guarantors (or any such successor
entity), as such, shall have any liability for any Obligations of the Guarantors
under this Supplemental Indenture or the Indenture or for any claim based on, in
respect of, or by reason of, such Obligations or their creation, except in their
capacity as an obligor or Guarantor of the Notes in accordance with the
Indenture.

         This is a continuing Guarantee and shall remain in full force and
effect and shall be binding upon the Guaranteeing Subsidiaries and their
successors and assigns until full and final payment of all of the Company's
obligations under the Notes and Indenture or until released in accordance with
the Indenture and shall inure to the benefit of the successors and assigns of
the Trustee and the Holders, and, in the event of any transfer or assignment of
rights by any Holder or the Trustee, the rights and privileges herein conferred
upon that party shall automatically extend to and be vested in such transferee
or assignee, all subject to the terms and conditions hereof. This is a Guarantee
of payment and not of collectibility.

         The Obligations of the Guaranteeing Subsidiaries under this
Supplemental Indenture shall be limited to the extent necessary to ensure that
they do not constitute a fraudulent conveyance under applicable law.

         THE TERMS OF ARTICLE X OF THE INDENTURE ARE INCORPORATED HEREIN BY
REFERENCE.

                                      -2-

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         3. NEW YORK LAW TO GOVERN. THE INTERNAL LAW OF THE STATE OF NEW YORK
SHALL GOVERN AND BE USED TO CONSTRUE THIS SUPPLEMENTAL INDENTURE, INCLUDING,
WITHOUT LIMITATION, SECTION 5-1401 OF THE NEW YORK GENERAL OBLIGATIONS LAW.

         4. Counterparts. The parties may sign any number of copies of this
Supplemental Indenture. Each signed copy shall be an original, but all of them
together represent the same agreement.

         5. Effect of Headings. The Section headings herein are for convenience
only and shall not affect the construction hereof.

                                      -3-

<PAGE>   4

         IN WITNESS WHEREOF, the parties hereto have caused this Supplemental
Indenture to be duly executed and attested, all as of the date first above
written.

                                    THE COMPANY:

                                    HORSESHOE GAMING HOLDING CORP.

                                    By:
                                        ------------------------------------
                                             Name: Jack B. Binion
                                             Title:   President

                                    THE GUARANTEEING SUBSIDIARIES:

                                    HORSESHOE GP, INC.

                                    By:
                                        ------------------------------------
                                             Name: Jack B. Binion
                                             Title:   President

                                    NEW GAMING CAPITAL PARTNERSHIP

                                    By:      HORSESHOE GP, INC.,
                                             its General Partner

                                             -------------------------------
                                             Name: Jack B. Binion
                                             Title:   President

                                      -4-
<PAGE>   5

                                   HORSESHOE ENTERTAINMENT

                                   By:      NEW GAMING CAPITAL PARTNERSHIP,
                                            its General Partner

                                   By:      HORSESHOE GP, INC.,
                                            its General Partner

                                            -------------------------------
                                            Name: Jack B. Binion
                                            Title:   President

                                   HORSESHOE GAMING, L.L.C.

                                   By:      HORSESHOE GAMING HOLDING CORP.,
                                            its Managing Member

                                            ---------------------------------
                                            Name: Jack B. Binion
                                            Title:   President

                                   EMPRESS CASINO HAMMOND CORPORATION

                                   By:
                                       ------------------------------------
                                            Name: Jack B. Binion
                                            Title:   President

                                   EMPRESS CASINO JOLIET CORPORATION

                                   By:_________________________________
                                            Name: Jack B. Binion
                                            Title:   President

                                      -5-
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                                   HAMMOND RESIDENTIAL, L.L.C.

                                   By:      EMPRESS CASINO HAMMOND
                                            CORPORATION,
                                            its Managing Member

                                            ---------------------------------
                                            Name: Jack B. Binion
                                            Title:   President

                                   ROBINSON PROPERTY GROUP LIMITED PARTNERSHIP

                                    By:    HORSESHOE GP, INC.,
                                           its General Partner

                                           -------------------------------
                                           Name: Jack B. Binion
                                           Title:   President

                                    BOSSIER CITY LAND CORPORATION

                                    By:
                                        ------------------------------------
                                           Name: Jack B. Binion
                                           Title:   President

                                    TRUSTEE:

                                    U.S. TRUST COMPANY,
                                    NATIONAL ASSOCIATION

                                    By:
                                        ------------------------------------
                                           Name:
                                           Title:

                                      -6-

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