SEC FORM 4

SEC Form 4

FORM 4

UNITED STATES SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP

Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934
or Section 30(h) of the Investment Company Act of 1940

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Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).

1. Name and Address of Reporting Person^*

SIMBERG BRUCE

(Last)

(First)

(Middle)

3661 WEST OAKLAND PARK BLVD

SUITE 300

(Street)

LAUDERDALE LAKES

33311

(City)

(State)

(Zip)

2. Issuer Name and Ticker or Trading Symbol
21ST CENTURY HOLDING CO [ TCHC ]

5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)

X	Director	10% Owner
	Officer (give title below)	Other (specify below)

3. Date of Earliest Transaction (Month/Day/Year)
02/21/2008

4. If Amendment, Date of Original Filed (Month/Day/Year)

6. Individual or Joint/Group Filing (Check Applicable Line)

X	Form filed by One Reporting Person
	Form filed by More than One Reporting Person

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)
1. Title of Security (Instr. 3)	2. Transaction Date (Month/Day/Year)	2A. Deemed Execution Date, if any (Month/Day/Year)	Code	V	Amount	(A) or (D)	Price		6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	7. Nature of Indirect Beneficial Ownership (Instr. 4)
Common Stock	02/21/2008		X		9,430	A	$6.667	146,680	D
Common Stock	02/21/2008		S		1,690	D	$13.4512	144,990	D
Common Stock	02/21/2008		S		1,000	D	$13.453	143,990	D
Common Stock	02/21/2008		S		1,000	D	$13.454	142,990	D
Common Stock	02/21/2008		S		1,000	D	$13.456	141,990	D
Common Stock	02/21/2008		S		1,000	D	$13.457	140,990	D
Common Stock	02/21/2008		S		1,000	D	$13.462	139,990	D
Common Stock	02/21/2008		S		1,000	D	$13.483	138,990	D
Common Stock	02/21/2008		S		1,000	D	$13.5002	137,990	D
Common Stock	02/21/2008		S		740	D	$13.5268	137,250	D
Common Stock	02/22/2008		X		4,070	A	$6.667	141,320	D
Common Stock	02/22/2008		X		1,030	A	$8.333	142,350	D
Common Stock	02/22/2008		S		686	D	$13.11	141,664	D
Common Stock	02/22/2008		S		114	D	$13.12	141,550	D
Common Stock	02/22/2008		S		1,000	D	$13.16	140,550	D
Common Stock	02/22/2008		S		700	D	$13.26	139,850	D
Common Stock	02/22/2008		S		200	D	$13.27	139,650	D
Common Stock	02/22/2008		S		1,000	D	$13.3	138,650	D
Common Stock	02/22/2008		S		1,400	D	$13.33	137,250	D

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 Securities Underlying Derivative Security (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: Direct (D) or Indirect (I) (Instr. 4)	11. Nature of Indirect Beneficial Ownership (Instr. 4)
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)	Code	V	(A)	(D)	Date Exercisable	Expiration Date	Title	Amount or Number of Shares	8. Price of Derivative Security (Instr. 5)		10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	11. Nature of Indirect Beneficial Ownership (Instr. 4)
Options	$6.667	02/21/2008		X			4,500	11/05/1999⁽¹⁾	11/05/2008	Common Stock	4,500	$6.667	0	D
Options	$6.667	02/21/2008		X			4,500	06/06/2001⁽¹⁾	06/06/2010	Common Stock	4,500	$6.667	0	D
Options	$6.667	02/21/2008		X			430	06/05/2002⁽¹⁾	06/05/2011	Common Stock	430	$6.667	4,070	D
Options	$6.667	02/22/2008		X			4,070	06/05/2002⁽¹⁾	06/05/2011	Common Stock	4,070	$6.667	0	D
Options	$8.333	02/22/2008		X			1,030	06/04/2003⁽¹⁾	06/04/2011	Common Stock	1,030	$8.333	13,970	D
Options	$15.79							12/05/2006⁽²⁾	12/05/2011	Common Stock	10,000		10,000	D
Options	$13.17							12/06/2008⁽²⁾	12/06/2013	Common Stock	500		500	D
Options	$12.58							01/30/2009⁽²⁾	01/30/2014	Common Stock	4,500		4,500	D

Explanation of Responses:

1. Options are fully vested.

2. Options vest 20% per year.

Remarks:

	Bruce Simberg	02/25/2008
	** Signature of Reporting Person	Date
Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
* 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).
Note: File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure.
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