<Page>
Exhibit 4.14
STOCK PURCHASE AGREEMENT
THIS AGREEMENT (this "Agreement"), is made as of March 26, 2002, by
and among (i) Von Hoffmann Holdings Inc., a Delaware corporation (formerly Von
Hoffmann Corporation, the "Company"), and (ii) DLJ Merchant Banking Partners II,
L.P., DLJ Merchant Banking Partners II-A, L.P., DLJ Offshore Partners II, C.V.,
DLJ Diversified Partners, L.P., DLJ Diversified Partners-A, L.P., DLJ Millennium
Partners, L.P., DLJ Millennium Partners-A, L.P., DLJ EAB Partners, and
Donaldson, Lufkin & Jenrette Securities Corporation (collectively, the
"Purchasers" and, each individually, a "Purchaser").
W I T N E S S E T H :
WHEREAS, upon the terms and subject to the conditions herein, the
Company proposes to sell up to an aggregate of 25,000,000 shares (the "Offered
Shares") of common stock, par value $.01 per share ("Common Stock"), of the
Company.
NOW, THEREFORE, in order to implement the foregoing and in
consideration of the mutual representations, warranties, covenants and
agreements contained herein and for other good and valuable consideration, the
receipt and adequacy of which are hereby acknowledged, the parties hereto,
intending to be legally bound, hereby agree as follows:
1. PURCHASE AND SALE OF THE SECURITIES.
(a) At the Initial Closing (as defined in Section 2(a) below), subject
to the terms and conditions set forth herein, the Company shall sell to each
Purchaser, and each Purchaser shall purchase from the Company, the number of
shares of Common Stock listed opposite the name of such Purchaser in SCHEDULE I
(the "Initial Shares") for the purchase price listed opposite the name of such
Purchaser in SCHEDULE I (the "Initial Investment").
(b) Subject to the terms and conditions set forth herein, the
Purchasers may, at any time and from time to time, prior to December 31, 2002,
elect (by written notice to the Company), in their respective sole discretion,
to purchase in the aggregate up to 5,000,000 shares of Common Stock (the
"Optional Shares" and, together with the Initial Shares, the "Shares") for a
purchase price of $1.00 per share (any such purchase, an "Optional Investment")
in accordance with Section 2(b) below.
2. CLOSING.
(a) The closing (the "Initial Closing") of the Initial Investment
shall take place at the offices of Weil, Gotshal & Manges LLP, 767 Fifth Avenue,
New York, New York ("WGM"), at 9:00 a.m. (New York City time) on the date
hereof, or at such other place, or on such other date and time, as shall be
mutually agreeable to the parties hereto.
<Page>
(b) The closing(s) (each an "Optional Closing" and, together with the
Initial Closing, the "Closings"), if any, of an Optional Investment shall take
place, if and only if a Purchaser elects to proceed with the Optional
Investment, at the offices of WGM, at such time or times designated by such
Purchaser within five (5) business days after such Purchaser delivers to the
Company notice of its election to make an Optional Investment.
(c) At each Closing, the Company shall deliver to each Purchaser
certificates representing the Shares issued to such Purchaser, upon payment of
the purchase price therefor by delivery to the Company of the amount thereof by
wire transfer of immediately available funds to an account or accounts of the
Company designated in writing by the Company to such Purchaser prior to such
Closing.
3. CONDITIONS OF THE PURCHASERS' OBLIGATIONS AT EACH CLOSING. The
obligation of each Purchaser to purchase and pay for the Shares to be purchased
at each Closing is subject to the satisfaction as of such Closing of the
following conditions:
(a) The representations and warranties of the Company contained in
Section 5 hereof shall be true and correct in all material respects at and as of
such Closing as though then made.
(b) All corporate and other proceedings taken or required to be taken
in connection with the transactions contemplated hereby to be consummated at or
prior to such Closing and all documents incident thereto shall be satisfactory
in form and substance to the Purchasers.
4. CONDITIONS OF THE COMPANY'S OBLIGATIONS AT EACH CLOSING. The
obligation of the Company to issue and sell the Shares to a Purchaser upon a
Closing is subject to the satisfaction as of such Closing by such Purchaser of
the following conditions:
(a) The representations and warranties of such Purchaser contained in
Section 6 hereof shall be true and correct in all material respects at and as of
such Closing as though then made.
(b) Such Purchaser shall have delivered to the Company, in accordance
with Section 2(c) hereof, the applicable purchase price for the Shares being
purchased by such Purchaser.
5. REPRESENTATIONS AND WARRANTIES OF THE COMPANY. The Company
represents and warrants to each Purchaser as follows:
(a) the Company has full corporate power and authority to execute and
deliver this Agreement and to perform its obligations hereunder;
(b) this Agreement has been duly authorized, executed and delivered by
the Company;
2
<Page>
(c) assuming the due execution and delivery of this Agreement by the
other parties hereto, this Agreement constitutes the legal, valid and binding
obligation of the Company, enforceable against the Company in accordance with
its terms; and
(d) the Shares of Common Stock to be issued to each Purchaser pursuant
to this Agreement, when purchased, issued and delivered in accordance with the
terms hereof, will be duly and validly issued and will be fully paid and
nonassessable.
6. REPRESENTATIONS AND WARRANTIES OF THE PURCHASERS. Each Purchaser
hereby represents and warrants, severally and not jointly, to the Company that:
(a) such Purchaser has full power and authority to execute and deliver
this Agreement and to perform its obligations hereunder;
(b) this Agreement has been duly executed and delivered by or on
behalf of such Purchaser;
(c) assuming the due execution and delivery of this Agreement by the
other parties hereto, this Agreement constitutes the legal, valid and binding
obligation of such Purchaser, enforceable against such Purchaser in accordance
with its terms;
(d) such Purchaser is acquiring its respective Shares for investment
purposes only and not with a current view to the sale or distribution thereof;
such Purchaser's financial situation is such that such Purchaser can afford to
bear the economic risk of holding its Shares for an indefinite period of time
and suffer complete loss of such Purchaser's investment in its Shares; such
Purchaser's knowledge and experience in financial and business matters are such
that such Purchaser is capable of evaluating the merits and risks of such
Purchaser's investment in its Shares; such Purchaser understands that the Shares
are a speculative investment that involve a high degree of risk of loss of such
Purchaser's investment therein, that there are substantial restrictions on the
transferability of the Shares and that for an indefinite period there will be no
public market for the Shares and, accordingly, it may not be possible to
liquidate such Purchaser's investment in the Company in case of emergency, if at
all; in making such Purchaser's decision to invest in the Shares hereunder, such
Purchaser has relied upon independent investigations made by such Purchaser and,
to the extent believed by such Purchaser to be appropriate, such Purchaser's
representatives, including such Purchaser's own professional, tax and other
advisors; and such Purchaser and such Purchaser's representatives have been
given the opportunity to examine all documents and to ask questions of, and to
receive answers from, the Company and its representatives concerning the terms
and conditions of the investment in the Shares; and
(e) each Purchaser hereby acknowledges that it is fully familiar with
the Company and that no other representations or warranties, express or implied,
regarding the Company, its business, operations, plans or prospects have been
made to it by the Company or any other third party.
7. SUCCESSORS AND ASSIGNS. Except as otherwise expressly provided
herein, all covenants and agreements contained in this Agreement by or on behalf
of any
3
<Page>
of the parties hereto shall be binding on and inure to the benefit of the
respective successors and assigns of the parties hereto.
8. COUNTERPARTS. This Agreement may be executed in two or more
counterparts, each of which shall be considered an original, but all of which
taken together shall constitute one and the same Agreement.
9. DESCRIPTIVE HEADINGS. The descriptive headings of this Agreement
are inserted for convenience only and do not constitute a part of this
Agreement.
10. AMENDMENT/WAIVER. This agreement may amended, supplemented,
modified or changed only by a written agreement making specific reference to
this Agreement executed by the Company and the Purchasers; and any provision
hereof may be waived, in whole or part, only by a written agreement making
specific reference to this Agreement executed by the party making such waiver.
11. GOVERNING LAW. This Agreement shall be governed by the laws of the
State of New York, without regard to the conflicts of law principles thereof.
12. NOTICES. All notices and other communications hereunder shall be
in writing and shall be deemed to have been duly given if delivered, telecopied
or mailed, certified or registered mail, return receipt requested:
(a) If to any Purchaser, to:
DLJ Merchant Banking Partners II, L.P.
11 Madison Avenue
16th Floor
New York, NY 10010
Attention: David Burgstahler
Telecopy No.: (212) 325-5553
(b) If to the Company, to:
Von Hoffmann Holdings Inc.
1000 Camera Avenue
St. Louis, MO 63126-1019
Attention: Chief Executive Officer
Telecopy No.: (314) 966-0983
Such names and addresses may be changed by written notice to each person listed
above. All notices are effective upon receipt or upon refusal if properly
delivered.
4
<Page>
IN WITNESS WHEREOF, the parties hereto have executed this Agreement on the
date first written above.
VON HOFFMANN HOLDINGS INC.
By: /s/ Peter C. Mitchell
---------------------------
Name: Peter C. Mitchell
Title: Chief Financial Officer
DLJ MERCHANT BANKING PARTNERS II, L.P.
By: DLJ MERCHANT BANKING II, INC.,
Managing General Partner
By: /s/ Michael Isikow
---------------------------
Name: Michael Isikow
Title: Vice President
DLJ DIVERSIFIED PARTNERS, L.P.
By: DLJ DIVERSIFIED PARTNERS, INC.
By: /s/ Michael Isikow
---------------------------
Name: Michael Isikow
Title: Vice President
DLJ EAB PARTNERS, L.P.
By: DLJ LBO PLANS MANAGEMENT
CORPORATION
Managing General Partner
By: /s/ Michael Isikow
---------------------------
Name: Michael Isikow
Title: Vice President
DLJ OFFSHORE PARTNERS II, C.V.
By: DLJ MERCHANT BANKING II, INC.,
Managing General Partner
By: /s/ Michael Isikow
---------------------------
Name: Michael Isikow
Title: Vice President
5
<Page>
DLJ DIVERSIFIED PARTNERS-A, L.P.
By: DLJ DIVERSIFIED PARTNERS, INC.
Managing General Partner
By: /s/ Michael Isikow
--------------------------
Name: Michael Isikow
Title: Vice President
DLJ MERCHANT BANKING PARTNERS II-A, L.P.
By: DLJ MERCHANT BANKING II, INC., Managing
General Partner
By: /s/ Michael Isikow
--------------------------
Name: Michael Isikow
Title: Vice President
DLJ MILLENNIUM PARTNERS, L.P.
By: DLJ MERCHANT BANKING II, INC., Managing
General Partner
By: /s/ Michael Isikow
--------------------------
Name: Michael Isikow
Title: Vice President
6
<Page>
DLJ MILLENNIUM PARTNERS-A L.P.
By: DLJ MERCHANT BANKING II, INC., Managing
General Partner
By: /s/ Michael Isikow
---------------------------
Name: Michael Isikow
Title: Vice President
DONALDSON, LUFKIN & JENRETTE SECURITIES
CORPORATION
By: /s/ Michael Isikow
---------------------------
Name: Michael Isikow
Title: Vice President
7
<Page>
SCHEDULE I
TO
STOCK PURCHASE AGREEMENT
<Table>
<Caption>
PURCHASER NUMBER OF SHARES PURCHASE PRICE
DLJ Merchant Banking Partners II, L.P. 12,598,505 $ 12,598,505
DLJ Merchant Banking Partners II-A, L.P. 501,731 $ 501,731
DLJ Offshore Partners II, C.V. 619,529 $ 619,529
DLJ Diversified Partners, L.P. 736,566 $ 736,566
DLJ Diversified Partners-A, L.P. 273,535 $ 273,535
DLJ Millennium Partners, L.P. 203,704 $ 203,704
DLJ Millennium Partners-A, L.P. 39,731 $ 39,731
DLJ EAB Partners, L.P. 56,566 $ 56,566
Donaldson, Lufkin & Jenrette Securities
Corporation 4,970,133 $ 4,970,133
TOTAL: 20,000,000 $ 20,000,000
</Table>
8