Ownership Submission
FORM 4
Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).
UNITED STATES SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP OF SECURITIES

Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934, Section 17(a) of the Public Utility Holding Company Act of 1935 or Section 30(h) of the Investment Company Act of 1940
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(Print or Type Responses)
1. Name and Address of Reporting Person *
WHITEBOX ADVISORS LLC
  2. Issuer Name and Ticker or Trading Symbol
21ST CENTURY HOLDING CO [TCHC]
5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)
_____ Director __X__ 10% Owner
_____ Officer (give title below) _____ Other (specify below)
(Last)
(First)
(Middle)
3033 EXCELSIOR BOULEVARD, SUITE 300
3. Date of Earliest Transaction (Month/Day/Year)
12/10/2004
(Street)

MINNEAPOLIS, MN 55416
4. If Amendment, Date Original Filed(Month/Day/Year)
6. Individual or Joint/Group Filing(Check Applicable Line)
___ Form filed by One Reporting Person
_X_ Form filed by More than One Reporting Person
(City)
(State)
(Zip)
Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned
1.Title of Security
(Instr. 3)
2. Transaction Date (Month/Day/Year) 2A. Deemed Execution Date, if any (Month/Day/Year) 3. Transaction Code
(Instr. 8)
4. Securities Acquired (A) or Disposed of (D)
(Instr. 3, 4 and 5)
5. Amount of Securities Beneficially Owned Following Reported Transaction(s)
(Instr. 3 and 4)
6. Ownership Form: Direct (D) or Indirect (I)
(Instr. 4)
7. Nature of Indirect Beneficial Ownership
(Instr. 4)
Code V Amount (A) or (D) Price
Common Stock (1) 10/01/2004   S   1,000 D $ 11.23 887,006 I (6) (7) (8) Refer footnote (6) (7) (8)
Common Stock (1) 10/04/2004   S   1,700 D $ 11.1 885,306 I Refer footnote (6) (7) (8)
Common Stock (1) 10/05/2004   S   191 D $ 10.9 885,115 I Refer footnote (6) (7) (8)
Common Stock (1) 10/06/2004   S   3,200 D $ 10.87 881,915 I Refer footnote (6) (7) (8)
Common Stock (2) 10/06/2004   S   1,000 D $ 10.86 880,915 I Refer footnote (6) (7) (8)
Common Stock (4) 10/06/2004   S   1,000 D $ 10.86 879,915 I Refer footnote (6) (7) (8)
Common Stock (1) 10/08/2004   S   1,000 D $ 10.98 878,915 I Refer footnote (6) (7) (8)
Common Stock (3) 10/08/2004   S   1,000 D $ 10.95 877,915 I Refer footnote (6) (7) (8)
Common Stock (1) 10/12/2004   S   1,900 D $ 10.93 876,015 I Refer footnote (6) (7) (8)
Common Stock (1) 10/14/2004   S   2,410 D $ 10.89 873,605 I Refer footnote (6) (7) (8)
Common Stock (3) 10/14/2004   S   1,000 D $ 10.91 872,605 I Refer footnote (6) (7) (8)
Common Stock (1) 10/15/2004   S   3,000 D $ 10.61 869,605 I Refer footnote (6) (7) (8)
Common Stock (1) 10/19/2004   S   2,585 D $ 10.27 867,020 I Refer footnote (6) (7) (8)
Common Stock (1) 10/26/2004   S   1,100 D $ 10.62 863,460.75 I Refer footnote (6) (7) (8)
Common Stock (1) 11/01/2004   J   18,453 (5) A $ 10.1156 880,278 I Refer footnote (6) (7) (8)
Common Stock (2) 11/01/2004   J   18,453 (5) A $ 10.1156 898,731 I Refer footnote (6) (7) (8)
Common Stock (3) 11/01/2004   J   9,227 (5) A $ 10.1156 907,958 I Refer footnote (6) (7) (8)
Common Stock (1) 12/10/2004   S   3,400 (5) D $ 13.0318 904,558 I Refer footnote (6) (7) (8)

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Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned
(e.g., puts, calls, warrants, options, convertible securities)
1. Title of Derivative Security
(Instr. 3)
2. Conversion or Exercise Price of Derivative Security 3. Transaction Date (Month/Day/Year) 3A. Deemed Execution Date, if any (Month/Day/Year) 4. Transaction Code
(Instr. 8)
5. Number of Derivative Securities Acquired (A) or Disposed of (D)
(Instr. 3, 4, and 5)
6. Date Exercisable and Expiration Date
(Month/Day/Year)
7. Title and Amount of Underlying Securities
(Instr. 3 and 4)
8. Price of Derivative Security
(Instr. 5)
9. Number of Derivative Securities Beneficially Owned Following Reported Transaction(s)
(Instr. 4)
10. Ownership Form of Derivative Security: Direct (D) or Indirect (I)
(Instr. 4)
11. Nature of Indirect Beneficial Ownership
(Instr. 4)
Code V (A) (D) Date Exercisable Expiration Date Title Amount or Number of Shares
Redeemable Warrants (Right to Buy) (1) $ 12.74 10/21/2004   S     900 07/31/2003 07/31/2006 Common Stock 675 $ 2.75 477,228 I Refer footnote (6) (7) (8)
Redeemable Warrants (Right to Buy) (1) $ 12.74 10/26/2004   S     1,379 07/31/2003 07/31/2006 Common Stock 1,034.25 $ 2.9 475,849 I Refer footnote (6) (7) (8)
Redeemable Warrants (Right to Buy) (2) $ 12.74 10/26/2004   S     1,000 07/31/2003 07/31/2006 Common Stock 750 $ 2.9 474,849 I Refer footnote (6) (7) (8)
Redeemable Warrants (Right to Buy) (1) $ 12.74 10/27/2004   S     281 07/31/2003 07/31/2006 Common Stock 210.75 $ 3.1 474,568 I Refer footnote (6) (7) (8)
Redeemable Warrants (Right to Buy) (3) $ 12.74 10/28/2004   S     1,500 07/31/2003 07/31/2006 Common Stock 1,125 $ 2.9 473,068 I Refer footnote (6) (7) (8)
Redeemable Warrants (Right to Buy) (3) $ 12.74 11/01/2004   S     400 07/31/2003 07/31/2006 Common Stock 300 $ 2.82 472,668 I Refer footnote (6) (7) (8)

Reporting Owners

Reporting Owner Name / Address Relationships
 Director  10% Owner  Officer  Other
WHITEBOX ADVISORS LLC
3033 EXCELSIOR BOULEVARD, SUITE 300
MINNEAPOLIS, MN 55416
    X    
Whitebox Convertible Arbitrage Advisors, LLC
3033 EXCELSIOR BOULEVARD, SUITE 300
MINNEAPOLIS, MN 55416
    X    
Whitebox Convertible Arbitrage Partners, L.P.
3033 EXCELSIOR BOULEVARD, SUITE 300
MINNEAPOLIS, MN 55416
    X    
Whitebox Convertible Arbitrage Fund, L.P.
3033 EXCELSIOR BOULEVARD, SUITE 300
MINNEAPOLIS, MN 55416
    X    
Whitebox Convertible Arbitrage Fund, Ltd.
3033 EXCELSIOR BOULEVARD, SUITE 300
MINNEAPOLIS, MN 55416
    X    
Whitebox Hedged High Yield Advisors, LLC
3033 EXCELSIOR BOULEVARD, SUITE 300
MINNEAPOLIS, MN 55416
    X    
Whitebox Hedged High Yield Partners, L.P.
3033 EXCELSIOR BOULEVARD, SUITE 300
MINNEAPOLIS, MN 55416
    X    
Whitebox Hedged High Yield Fund, L.P.
3033 EXCELSIOR BOULEVARD, SUITE 300
MINNEAPOLIS, MN 55416
    X    
Whitebox Hedged High Yield Fund, Ltd.
3033 EXCELSIOR BOULEVARD, SUITE 300
MINNEAPOLIS, MN 55416
    X    
Whitebox Intermarket Advisors, LLC
3033 EXCELSIOR BOULEVARD, SUITE 300
MINNEAPOLIS, MN 55416
    X    

Signatures

 /s/ Jonathan D. Wood, Chief Financial Officer for Whitebox Advisors, LLC   01/28/2005
**Signature of Reporting Person Date

Explanation of Responses:

* If the form is filed by more than one reporting person, see Instruction 4(b)(v).
** Intentional misstatements or omissions of facts constitute Federal Criminal Violations. See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).
(1) Reporting Person is Whitebox Convertible Arbitrage Partners, L.P. ("WCAP").
(2) Reporting Person is Whitebox Hedged High Yield Partners, L.P. ("WHHYP").
(3) Reporting Person is Pandora Select Partners, L.P. ("PSP").
(4) Reporting Person is Whitebox Intermarket Partners, L.P. ("WIP").
(5) Restricted stock received as interest payment pursuant to the 6% Senior Subordinated Notes entered into between Company and the reporting person.
(6) The general partner of WCAP, is Whitebox Convertible Arbitrage Advisors, LLC ("WCAA"), which manages accounts for the benefit of its clients WCAP, Whitebox Convertible Arbitrage Fund, L.P. ("WCAFLP") and Whitebox Convertible Arbitrage Fund, Ltd. ("WCAFLTD"); the general partner of WHHYP is Whitebox Hedged High Yield Advisors, LLC ("WHHYA"), which manages accounts for the benefit of its clients WHHYP, Whitebox Hedged High Yield Fund, L.P. ("WHYYFLP") and Whitebox Hedged High Yield Fund, Ltd. ("WHHYFLTD"); the general partner of WIP is Whitebox Intermarket Advisors, LLC ("WIA"), which manages accounts for the benefit of its clients WIP, Whitebox Intermarket Fund, L.P. ("WIFLP") and Whitebox Intermarket Fund, Ltd. ("WIFLTD"). The managing member and controlling owner of each of WCAA, WHHYA and WIA is Whitebox Advisors, LLC. (Cont. in footnote 7)
(7) The general partner of PSP is Pandora Select Advisors, LLC ("PSA"), which manages accounts for the benefit of its clients PSP, Pandora Select Fund, L.P. ("PSFLP")and Pandora Select Fund, Ltd. ("PSFLTD"). The managing member and controlling owner of PSA is AJR Financial, LLC. Whitebox Advisors, LLC and AJR Financial, LLC each have the same sole owner and managing member. (Cont. in footnote 8)
(8) Based on the relationships described herein, these entities may be deemed to constitute a "group" within the meaning of Rule 13d-5(b)(1) under the Securities Exchange Act of 1934. The filing of this statement shall not be construed as an admission that Whitebox Advisors, LLC, AJR Financial, LLC, WCCA, WHHYA, WIA, PSA, WCAP, WHHYP, WIP, PSP, WCAFLP, WHHYFLP, WIFLP, PSFLP, WCAFLTD, WHHYFLTD, WIFLTD and PSFLTD are a group, or have agreed to act as a group. Whitebox Advisors, LLC, AJR Financial, LLC, WCCA, WHHYA, WIA, PSA, WCAP, WHHYP, WIP, PSP, WCAFLP, WHHYFLP, WIFLP, PSFLP, WCAFLTD, WHHYFLTD, WIFLTD and PSFLTD each disclaim beneficial ownership of such shares of common stock except to the extent of their pecuniary interest in such shares.

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