DKNG Form 4: Kalish exercises options at $3.29 and executes 10b5-1 sales ~ $42.8

Rhea-AI Filing Summary

Matthew Kalish, President - DraftKings North America, reported multiple equity transactions. He received 28,309 shares from vested RSUs and had 13,688 shares withheld for taxes. On 08/11/2025 and 08/12/2025 he exercised stock options to acquire 210,000 shares on each date at an exercise price of $3.29 and contemporaneously sold 210,000 shares on each date at weighted-average prices of $42.68 and $42.90, respectively. Following the reported transactions the Form shows beneficial ownership figures of 4,400,233 shares after acquisitions and 4,190,233 shares after the sales. The filing also discloses indirect holdings of 196,309 and 2,938 shares held in family trusts.

Positive

• Acquired shares via option exercises totaling 420,000 shares at a $3.29 exercise price, demonstrating vesting/option realization.
• Received 28,309 shares from RSU vesting (net of withholding arrangements), increasing share ownership before subsequent sales.
• Filing discloses indirect holdings of 196,309 and 2,938 shares in family trusts, enhancing transparency of beneficial ownership.

Negative

• Sold 420,000 shares in aggregate under a Rule 10b5-1 plan at weighted-average prices around $42.7–$42.9, reducing direct shareholdings.
• 13,688 shares were withheld to satisfy tax obligations upon RSU vesting, lowering the net issuance received by the reporting person.

Insights

Securities Analyst

TL;DR: Insider exercised low-strike options and executed large pre-arranged sales, leaving roughly 4.19M shares beneficially owned.

The filing documents material option exercises at a $3.29 strike for two tranches of 210,000 shares each and near-simultaneous sales at weighted-average prices near $42.7–$42.9. The trades include RSU vesting of 28,309 shares with 13,688 withheld for taxes. Such activity increases realized liquidity for the reporting person while leaving reported beneficial ownership at 4,190,233 shares after the sales. Transactions were executed under a Rule 10b5-1 plan where specified.

Corporate Governance Expert

TL;DR: Transactions executed under pre-arranged plan and standard vesting/option mechanics; disclosure is routine and complete.

The Form 4 discloses RSU vesting, option exercises, cash payment of exercise prices and tax withholdings, plus sales conducted pursuant to a Rule 10b5-1 selling program. The report provides exercise prices ($3.29), weighted-average sale prices ($42.39–$43.18 and $42.48–$43.18 ranges cited), and post-transaction beneficial ownership figures. From a governance standpoint, the filing documents compliance with reporting obligations and identifies indirect holdings via family trusts.

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

OMB APPROVAL

OMB Number:			3235-0287
Estimated average burden
hours per response:			0.5

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

X

Check this box to indicate that a transaction was made pursuant to a contract, instruction or written plan for the purchase or sale of equity securities of the issuer that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c). See Instruction 10.

1. Name and Address of Reporting Person^*

Kalish Matthew

(Last) (First) (Middle)

C/O DRAFTKINGS INC.

222 BERKELEY STREET, 5TH FLOOR

(Street)

BOSTON MA 02116

(City) (State) (Zip)

2. Issuer Name and Ticker or Trading Symbol
DraftKings Inc. [ DKNG ]

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

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

3. Date of Earliest Transaction (Month/Day/Year)
08/09/2025

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)
			Code	V	Amount	(A) or (D)	Price
Class A Common Stock	08/09/2025		M		28,309	A	(1)	4,203,921	D
Class A Common Stock	08/09/2025		F		13,688	D	$42.88	4,190,233	D
Class A Common Stock	08/11/2025		M		210,000(2)	A	$3.29	4,400,233	D
Class A Common Stock	08/11/2025		S		210,000(3)	D	$42.68(4)	4,190,233	D
Class A Common Stock	08/12/2025		M		210,000(2)	A	$3.29	4,400,233	D
Class A Common Stock	08/12/2025		S		210,000(3)	D	$42.9(5)	4,190,233	D
Class A Common Stock								196,309	I	Held by Kalish Family 2020 Irrevocable Trusts
Class A Common Stock								2,938	I	Held by Matthew P. Kalish 2020 Trust

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)
				Code	V	(A)	(D)	Date Exercisable	Expiration Date	Title	Amount or Number of Shares
Restricted Stock Units	(1)	08/09/2025		M			28,309	(6)	(6)	Class A Common Stock	28,309	$0.00	56,617	D
Stock option	$3.29	08/11/2025		M			210,000	(7)	05/03/2028	Class A Common Stock	210,000	$0.00	483,488	D
Stock option	$3.29	08/12/2025		M			210,000	(7)	05/03/2028	Class A Common Stock	210,000	$0.00	273,488	D

Explanation of Responses:

1. No shares of Class A Common Stock were transferred or sold upon the vesting of the restricted stock units ("RSUs") other than to the Issuer to satisfy withholding taxes. The Reporting Person received the net of the 28,309 shares of Class A Common Stock underlying the RSUs listed in Table II, and 13,688 shares of Class A Common Stock withheld by the Issuer. Each RSU represents a contingent right to receive one share of the Issuer's Class A Common Stock.

2. The Reporting Person acquired shares of Class A Common Stock of the Issuer after the exercise of stock options and paid the aggregate exercise price and the tax withholding in cash.

3. The reported sales were made pursuant to a pre-arranged program for selling shares of Class A Common Stock adopted on November 27, 2024 pursuant to Rule 10b5-1 under the Securities Exchange Act of 1934.

4. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $42.39 to $43.12, inclusive. The Reporting Person has provided to the Issuer, and undertakes to provide any security holder of the Issuer or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in footnotes 4 and 5 to this Form 4.

5. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions ranging from $42.48 to $43.18, inclusive. See the last sentence of footnote 4 to this Form 4 above.

6. On February 9, 2022, the Reporting Person was granted 452,940 RSUs vesting quarterly over four (4) years.

7. These stock options were granted on May 3, 2018. As of the date hereof, all of such remaining stock options have vested.

Remarks:

President - DraftKings, North America

	/s/ Faisal Hasan, attorney-in-fact	08/12/2025
	** 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.
Persons who respond to the collection of information contained in this form are not required to respond unless the form displays a currently valid OMB Number.

FAQ

What transactions did Matthew Kalish report on the DKNG Form 4?

He reported RSU vesting of 28,309 shares, withholding of 13,688 shares for taxes, option exercises acquiring 210,000 shares on 08/11/2025 and 210,000 shares on 08/12/2025 at $3.29, and sales of 210,000 shares on each exercise date at weighted-average prices of about $42.68 and $42.90.

How many shares did Kalish beneficially own after the reported transactions?

The Form shows beneficial ownership figures of 4,400,233 shares following the acquisitions and 4,190,233 shares following the sales.

Were any sales executed under a pre-arranged plan (10b5-1)?

Yes. The reported sales of shares on the exercise dates were made pursuant to a pre-arranged Rule 10b5-1 selling program adopted on November 27, 2024.

What were the exercise prices and tax actions disclosed?

Stock options were exercised at an exercise price of $3.29. The issuer withheld 13,688 shares to satisfy tax withholding on RSU vesting.

Does the filing disclose any indirect holdings?

Yes. The filing discloses indirect beneficial holdings of 196,309 shares held by Kalish Family 2020 Irrevocable Trusts and 2,938 shares held by the Matthew P. Kalish 2020 Trust.