WRC MEDIA INC. REDEMPTION AND REPURCHASE AGREEMENT

REDEMPTION AND REPURCHASE AGREEMENT (as the same may hereafter be amended, supplemented or modified, this “ Agreement ”), dated as of June 22, 2005, among WRC MEDIA INC., a Delaware corporation (together with its successors and permitted assigns, “ WRC ”), THE NORTHWESTERN MUTUAL LIFE INSURANCE COMPANY, a Wisconsin corporation (together with its successors and permitted assigns, “ NML ”); ARES LEVERAGED INVESTMENT FUND, L.P., a Delaware limited partnership, ARES LEVERAGED INVESTMENT FUND II, L.P., a Delaware limited partnership (collectively, with their respective successors and permitted assigns, the “ Ares Funds ”); TCW/CRESCENT MEZZANINE PARTNERS II, L.P., a Delaware limited partnership, TCW/CRESCENT MEZZANINE TRUST II, a Delaware business trust, SHARED OPPORTUNITY FUND IIB, L.L.C., a Delaware limited liability company, TCW SHARED OPPORTUNITY FUND III, L.P., a Delaware limited liability company, TCW LEVERAGED INCOME TRUST II, L.P., a Delaware limited partnership, TCW LEVERAGED INCOME TRUST, L.P., a Delaware limited partnership (collectively, with their respective successors and permitted assigns, the “ TCW Funds ”); DLJ INVESTMENT PARTNERS II, L.P., a Delaware limited partnership, DLJ INVESTMENT PARTNERS, L.P., a Delaware limited partnership, and DLJIP II HOLDINGS, L.P., a Delaware limited partnership (collectively, with their respective successors and permitted assigns, the “ DLJ IP Funds ” and collectively, with NML, the Ares Funds and the TCW Funds, the “ Other Exchangers ”); and DLJ MERCHANT BANKING PARTNERS II, L.P., a Delaware limited partnership, DLJ MERCHANT BANKING PARTNERS II-A, L.P., a Delaware limited partnership, DLJ MERCHANT BANKING II, INC., a Delaware corporation, as Advisory General Partner on behalf of DLJ OFFSHORE PARTNERS II, C.V., a Netherlands Antilles limited partnership, DLJ DIVERSIFIED PARTNERS, L.P., a Delaware limited partnership, DLJ DIVERSIFIED PARTNERS-A, L.P., a Delaware limited partnership, DLJMB FUNDING II, INC., a Delaware corporation, DLJ MILLENNIUM PARTNERS, L.P., a Delaware limited partnership, DLJ MILLENNIUM PARTNERS-A, L.P., a Delaware limited partnership, DLJ EAB PARTNERS, L.P., a Delaware limited partnership, DLJ ESC II, L.P., a Delaware limited partnership, and DLJ FIRST ESC, L.P., a Delaware limited partnership (each, together with its successors and permitted assigns, a “ DLJMB Entity ”, collectively, the “ DLJMB Entities ” and collectively, with the Other Exchangers, the “ Exchangers ”).

SECTION 1.01.    Definitions. The following terms, as used herein, have the following meanings:

SECTION 2.01.    Redemption and Repurchase. Upon the terms and subject to the conditions of this Agreement, WRC agrees to redeem and repurchase from each Exchanger, and each Exchanger severally agrees to surrender for redemption and sell to WRC, all of the Securities set forth opposite such Exchanger’s name on Schedule A hereto at the closing of the Redemption and Repurchase (the “ Closing ”). The aggregate consideration for the Securities to be paid or delivered to the Exchangers (the “ Consideration ”) is (a) at the Closing: (i) cash in an aggregate amount equal to $55,000,000, plus 50% of the Call Savings realized at or prior to the Closing, if any, (ii) $30,000,000 in principal amount of second lien term indebtedness having the terms set forth in Schedule 2.01 (“ Second Lien Term Loans ”) and (iii) a number of shares (the “ Exchange Shares ”) of common stock, par value $0.01 per share, of WRC (the “ Common Stock ”) to be determined such that upon the closing of the Sale, after giving effect to the Transactions and all related transactions (including the Note Redemption), the Exchange Shares would constitute an aggregate of 30% of the outstanding Common Stock, calculated on a fully diluted basis prior to the issuance of New Management Options and (b) thereafter, promptly following any purchase or redemption of any Senior Subordinated Notes by WRC, the Purchaser or any of their respective Affiliates, 50% of the Call Savings attributable, to such purchase or redemption. The Consideration shall be allocated to the Securities and each Exchanger as set forth on Schedule A hereto. The Consideration shall be paid or delivered, as applicable, as provided in Section 2.02 and Section 2.03.

SECTION 2.02.    Closing. The Closing shall take place at the offices of Cravath, Swaine & Moore LLP, Worldwide Plaza, 825 Eighth Avenue, New York, 

New York, concurrently with the consummation of the Sale, or at such other time or place as WRC and the Exchangers may agree. At the Closing:

(c)    WRC shall issue and deliver, or cause to be delivered, to each Exchanger, certificates or other appropriate documentation for the number of Exchange Shares set forth opposite such Exchanger’s name on Schedule A hereto, registered in the name of such Exchanger and bearing appropriate legends; and

(d)    Each Exchanger shall deliver, or cause to be delivered, to WRC, certificates or other appropriate documentation for the Securities set forth opposite such Exchanger’s name on Schedule A hereto, duly endorsed in blank or accompanied by instruments of transfer executed in blank.

SECTION 2.03.    Call Savings. If WRC, the Purchaser or any of their respective Affiliates purchases or redeems any Senior Subordinated Notes, WRC shall deliver, or cause to be delivered, to each Exchanger, in immediately available funds, such Exchanger’s Pro Rata Share of 50% of the portion of any Call Savings attributable to such purchase or redemption, by wire transfer (or other means acceptable to each Exchanger) to the account of such Exchanger with a bank in New York City designated by such Exchanger by notice to WRC prior to the Closing, it being understood that none of WRC, the Purchaser or any of their respective Affiliates shall have any obligation to take any action to realize any Call Savings in connection with such purchase or redemption.

SECTION 3.01.    Corporate Existence and Power. WRC is a corporation duly incorporated, validly existing and in good standing under the laws of Delaware and has all corporate powers and all material governmental licenses, authorizations, permits,

consents and approvals required to carry on its business as now conducted and as proposed to be conducted.

SECTION 3.02.    Corporate Authorization. The execution, delivery and performance by WRC of each of this Agreement, the Notes, the Note Agreement and the New Stockholders Agreement and the consummation by WRC of the transactions contemplated hereby and thereby (including the issuance of the Exchange Shares and the Note Redemption) are within the corporate powers of WRC and have been duly authorized by all necessary corporate action on the part of WRC. This Agreement and the New Stockholder Agreement each constitutes, and each Note and the Note Agreement when executed will constitute, a valid and binding agreement of WRC, each enforceable against WRC in accordance with its terms, except (i) as limited by applicable bankruptcy, insolvency, reorganization, moratorium, fraudulent transfer and other laws of general application affecting enforcement or creditors’ rights generally; (ii) as limited by laws relating to the availability of specific performance, injunctive relief or other equitable remedies; or (iii) as limited by general principles of equity, including without limitation, concepts of materiality, reasonableness, good faith and fair dealing, regardless of whether considered in a proceeding in equity or at law.

SECTION 3.03.    Governmental Authorization. The execution, delivery and performance by WRC of each of this Agreement, the Notes, the Note Agreement and the New Stockholders Agreement and the consummation of the transactions contemplated hereby and thereby require no order, license, consent, authorization or approval of, or exemption by, or action by or in respect of, or notice to, or filing or registration with, any governmental body, agency or official to be obtained or made by, or with respect to, WRC, except (i) as have been obtained or made (or are not required to be obtained or made until after the Closing), (ii) as required pursuant to the Securities Exchange Act of 1934 and (iii) filings of termination statements, mortgage releases, financing statements, mortgages and other notices in connection with the Refinancing and the Second Lien Term Loans.

SECTION 3.04.    Noncontravention. Except as set forth on Schedule 3.04 hereto, the execution, delivery and performance by WRC of each of this Agreement, the Notes, the Note Agreement and the New Stockholders Agreement and the consummation of the transactions contemplated hereby and thereby do not and will not (i) violate WRC’s certificate of incorporation or bylaws, (ii) violate any applicable law, rule, regulation, judgment, injunction, order or decree, (iii) require any consent or other action by any Person under, constitute a default under (with due notice or lapse of time or both), or give rise to any right of termination, cancellation or acceleration of any right or obligation of WRC or to a loss of any benefit to which WRC is entitled under any provision of any material agreement or other instrument binding upon WRC or any of WRC’s assets or properties or (iv) result in the creation or imposition of any material Lien on any of WRC’s properties or assets.

SECTION 3.05.    Capitalization and Voting Rights of WRC.  (a) The authorized capital stock of WRC as of May 31, 2005 consists of 20,000,000 shares of Common Stock and 20,000,000 shares of preferred stock, par value $0.01 per share (the  

 “ Preferred Stock ”), and the outstanding capital stock of WRC as of   May 31, 2005 consists of 7,008,406 shares of Common Stock and 3,547,980 shares of Preferred Stock.