Via Facsimile and U.S. Mail
Mail Stop 03-09


							April 27, 2005


Richard A. Widdicombe
Chief Executive Officer
21st Century Holding Company
3661 West Oakland Park Blvd., Suite 300
Lauderdale Lakes, FL 33311

Re:	21st Century Holding Company
	Preliminary Proxy Statement on Schedule 14A
	Filed April 12, 2005
	File Number 0-25001

Dear Mr. Widdicombe:

	We have reviewed your filing and have the following comments.
Where indicated, we think you should revise your document in
response
to these comments.  If you disagree, we will consider your
explanation as to why our comment is inapplicable or a revision is
unnecessary.  Please be as detailed as necessary in your
explanation.
In some of our comments, we may ask you to provide us with
supplemental information so we may better understand your
disclosure.
After reviewing this information, we may or may not raise
additional
comments.

	Please understand that the purpose of our review process is
to
assist you in your compliance with the applicable disclosure
requirements and to enhance the overall disclosure in your filing.
We look forward to working with you in these respects.  We welcome
any questions you may have about our comments or on any other
aspect
of our review.  Feel free to call us at the telephone numbers
listed
at the end of this letter.



SCHEDULE 14A

General
1. Please note that you are required to file with the Commission
any
written instructions, scripts, and outlines that will be used by
any
person that solicits proxies on behalf of 21st Century Holding
Company, through personal interview, telephone, or telegram, and
all
other soliciting material that will be furnished to 21st Century
stockholders.  See Rules 14a-6(b) and (c) of the Exchange Act of
1934.
2. Please revise your proxy statement to indicate for each
proposal
whether the board of directors has unanimously recommended that
the
stockholders vote for that proposal.
Beneficial Security Ownership, page 2
3. Please disclose the natural persons who have voting and
dispositive power over the shares held by Whitebox Advisors, LLC.

Proposal One: Election of Directors, page 4
4. Please note that Item 401 of Regulation S-K requires a brief
description of the business experience of your officers and
directors
during each of the last five years.  Please revise this section to
include the applicable dates for Carl Dorf and Peter J. Prygelski.

Proposal Two: Approval of the Possible Issuance of 20% ..., page
15
5. Supplementally, please provide us your analysis supporting your
determination that the incorporation of financial statements are
not
required.
6. Please compare the total number of outstanding shares that you
have committed to issue other than as a result of the private
placement with the shares you may have to issue as a result of the
private placement and that you are considering in this proposal.
This would include shares you would issue upon exercise of
warrants
to the holders of the notes and to the private placement agent as
well as shares you may issue in payment of dividends on the notes.
We understand that the number of shares you intend to issue in
lieu
of cash dividends and the extent of the anti-dilution adjustments
you
will make depend upon the market price of your common stock.
Provide
a range of possible outcomes based upon a range of common stock
prices above and below your current market price.  You may also
want
to consider historical prices in delineating a range.
7. Please quantify the percentage ownership of the holders of the
notes as a group assuming exercise of the warrants issued to them
and
the payment of dividends in cash and the percentage ownership of
the
placement agent, J. Giordano Securities, LLC assuming exercise of
their warrants.  Provide a possible range of outcomes using the
same
range of market prices applicable to the previous comment.  Also
identify any individual holders of notes who might possibly own
more
than 5% of the registrant`s outstanding shares under any of these
outcomes and also disclose the number & percentage of shares they
could hold.
8. Please revise to include a discussion of the registration
rights
as it relates to the common stock underlying the note payments and
the common stock should holders of the notes exercise the warrants
received in the private placement.  Additionally, please disclose
the
potential negative effects on the market for your shares as a
result
of the registration of shares for resale.

9. We note your statement, "[i]f the shareholders do not authorize
this issuance, the transactions will, nonetheless, be valid.  We
may,
however, be in violation of the Nasdaq requirements described
above,
which could be cited by Nasdaq as a basis for delisting our shares
from Nasdaq."  This seems inconsistent with your statement, "[t]he
terms of the Notes and the Warrants provide that we will not issue
shares to pay principal and interest on the notes or make anti-
dilution adjustments to the Warrants in violation of the Nasdaq
rule
described above."  Please revise your disclosure or advise us.
10. Please expand your disclosure of a possible delisting from
Nasdaq
to explain how it would negatively effect shareholders.
11. Please revise to disclose all of the potential negative
material
effects of failure to approve proposal two and how you will deal
with
any problems should they occur.
12. We note your disclosure in the second paragraph of this
proposal,
"and one warrant to purchase one share of our Common Stock (a
"Warrant")."  This seems inconsistent with your disclosure that
states you issued a total of 1,019,608 Warrants in the private
placement transaction.  Please revise your disclosure or advise
us.
13. Please disclose the number of warrants issued to your
placement
agent J. Giordano Securities, LLC and the number issued to the
purchasers in the private placement.
14. In your description of the private placement, please disclose
how
you have used the proceeds to date.

Proxy Card
15. We note that your proxy card grants discretionary authority to
vote on other matters as may properly come before the meeting.
Please make this discretionary authority a separate proposal that
shareholders can vote on.  Also, please note that such
discretionary
authority cannot be used to adjourn the meeting for the purpose of
soliciting additional votes.  If you anticipate that you may
adjourn
the meeting to solicit additional votes, revise to include a
separate
vote on this matter.
*	*	*

	As appropriate, please amend your proxy statement in response
to
these comments.  You may wish to provide us with marked copies of
the
amendment to expedite our review.  Please furnish a cover letter
with
your amendment that keys your responses to our comments and
provides
any requested supplemental information.  Detailed cover letters
greatly facilitate our review.  Please understand that we may have
additional comments after reviewing your amendment and responses
to
our comments.

	We urge all persons who are responsible for the accuracy and
adequacy of the disclosure in the filings reviewed by the staff to
be
certain that they have provided all information investors require.
Since the company and its management are in possession of all
facts
relating to a company`s disclosure, they are responsible for the
accuracy and adequacy of the disclosures they have made.

	In connection with responding to our comments, please
provide,
in writing, a statement from the company acknowledging that

* the company is responsible for the adequacy and accuracy of the
disclosure in the filings;
* staff comments or changes to disclosure in response to staff
comments in the filings reviewed by the staff do not foreclose the
Commission from taking any action with respect to the filing; and
* the company may not assert staff comments as a defense in any
proceeding initiated by the Commission or any person under the
federal securities laws of the United States.

	In addition, please be advised that the Division of
Enforcement
has access to all information you provide to the staff of the
Division of Corporation Finance in our review of your filing or in
response to our comments on your filing.

	Please contact Albert Lee at (202) 824-5219 or me at (202)
942-
1840 with any other questions.

								Sincerely,



								Jeffrey Riedler
								Assistant Director

cc:	Nina S. Gordon
	Broad and Cassel
	7777 Glades Road, Suite 300
	Boca Raton, Florida 33434

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Richard A. Widdicombe
21st Century Holding Company
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