0001047469-07-004575 Sample Contracts

Contract
Replacement Capital Covenant • May 23rd, 2007 • Lehman Brothers Holdings Inc • Security brokers, dealers & flotation companies

Replacement Capital Covenant, dated as of May 17, 2007 (this “Replacement Capital Covenant”), by Lehman Brothers Holdings Inc., a Delaware corporation (together with its successors and assigns, the “Corporation”), in favor of and for the benefit of each Covered Debtholder (as defined below).

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STOCK PURCHASE CONTRACT AGREEMENT between LEHMAN BROTHERS HOLDINGS INC. and U.S. BANK NATIONAL ASSOCIATION, as Stock Purchase Contract Agent Dated as of May 17, 2007
Stock Purchase Contract • May 23rd, 2007 • Lehman Brothers Holdings Inc • Security brokers, dealers & flotation companies • New York

STOCK PURCHASE CONTRACT AGREEMENT, dated as of May 17, 2007, between LEHMAN BROTHERS HOLDINGS INC., a Delaware corporation (the “Company”), having its principal office at 745 Seventh Avenue, New York, New York 10019, and U.S. Bank National Association, a national banking association, acting as stock purchase contract agent for the Holders of MCAPS (as defined herein) from time to time (the “Stock Purchase Contract Agent”).

COLLATERAL AGREEMENT among LEHMAN BROTHERS HOLDINGS INC. and THE BANK OF NEW YORK, as Collateral Agent and Securities Intermediary and U.S. BANK NATIONAL ASSOCIATION, as Stock Purchase Contract Agent Dated as of May 17, 2007
Collateral Agreement • May 23rd, 2007 • Lehman Brothers Holdings Inc • Security brokers, dealers & flotation companies • New York

COLLATERAL AGREEMENT dated as of May 17, 2007 among Lehman Brothers Holdings Inc., a Delaware corporation (the “Company”), The Bank of New York, as collateral agent (in such capacity, the “Collateral Agent”), and as securities intermediary (as defined in Section 8-102(a)(14) of the UCC) with respect to the Collateral Account (in such capacity, the “Securities Intermediary”), and U.S. Bank National Association, as stock purchase contract agent and as attorney-in-fact of the Holders from time to time of the Mandatory Capital Advantaged Preferred Securities (“MCAPS”SM) (in such capacity, the “Stock Purchase Contract Agent”) under the Stock Purchase Contract Agreement.

GUARANTEE AGREEMENT LEHMAN BROTHERS HOLDINGS CAPITAL TRUST VIII Dated as of May 17, 2007
Guarantee Agreement • May 23rd, 2007 • Lehman Brothers Holdings Inc • Security brokers, dealers & flotation companies • New York

This GUARANTEE AGREEMENT (the “Guarantee”), dated as of May 17, 2007, is executed and delivered by Lehman Brothers Holdings Inc., a Delaware corporation (the “Guarantor”), and U.S. Bank National Association, as trustee (the “Guarantee Trustee”), for the benefit of the Holders (as defined herein) from time to time of the Trust Securities (as defined herein) of Lehman Brothers Holdings Capital Trust VIII, a Delaware statutory trust (the “Trust”).

GUARANTEE AGREEMENT LEHMAN BROTHERS HOLDINGS CAPITAL TRUST VII Dated as of May 17, 2007
Guarantee Agreement • May 23rd, 2007 • Lehman Brothers Holdings Inc • Security brokers, dealers & flotation companies • New York

This GUARANTEE AGREEMENT (the “Guarantee”), dated as of May 17, 2007, is executed and delivered by Lehman Brothers Holdings Inc., a Delaware corporation (the “Guarantor”), and U.S. Bank National Association, as trustee (the “Guarantee Trustee”), for the benefit of the Holders (as defined herein) from time to time of the Trust Securities (as defined herein) of Lehman Brothers Holdings Capital Trust VII, a Delaware statutory trust (the “Trust”).

LEHMAN BROTHERS HOLDINGS INC. AND as Trustee TWELFTH SUPPLEMENTAL INDENTURE Dated as of May 17, 2007
Supplemental Indenture • May 23rd, 2007 • Lehman Brothers Holdings Inc • Security brokers, dealers & flotation companies • New York

THIS TWELFTH SUPPLEMENTAL INDENTURE, dated as of May 17, 2007, is between LEHMAN BROTHERS HOLDINGS INC., a corporation duly organized and existing under the laws of the State of Delaware (the “Company”), and U.S. BANK NATIONAL ASSOCIATION, a national banking association duly organized and existing under the laws of the United States of America, acting as Trustee under the Indenture referred to below(the “Trustee”), as supplemented hereby for purposes of the Junior Subordinated Debentures (as defined below).

COLLATERAL AGREEMENT among LEHMAN BROTHERS HOLDINGS INC. and THE BANK OF NEW YORK, as Collateral Agent and Securities Intermediary and U.S. BANK NATIONAL ASSOCIATION, as Stock Purchase Contract Agent Dated as of May 17, 2007
Collateral Agreement • May 23rd, 2007 • Lehman Brothers Holdings Inc • Security brokers, dealers & flotation companies • New York

COLLATERAL AGREEMENT dated as of May 17, 2007 among Lehman Brothers Holdings Inc., a Delaware corporation (the “Company”), The Bank of New York, as collateral agent (in such capacity, the “Collateral Agent”), and as securities intermediary (as defined in Section 8-102(a)(14) of the UCC) with respect to the Collateral Account (in such capacity, the “Securities Intermediary”), and U.S. Bank National Association, as stock purchase contract agent and as attorney-in-fact of the Holders from time to time of the Mandatory Capital Advantaged Preferred Securities (“MCAPS”SM) (in such capacity, the “Stock Purchase Contract Agent”) under the Stock Purchase Contract Agreement.

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