DraftKings (NASDAQ: DKNG) director enters prepaid forward on 1,912,236 shares

Rhea-AI Filing Summary

DraftKings Inc. director Matthew Kalish entered into a prepaid variable forward sale contract covering up to 1,912,236 shares of Class A Common Stock. He will receive a cash payment of $31,720,935.66 on May 18, 2026 in exchange for an obligation to deliver shares after May 18, 2029.

Kalish pledged 1,912,236 shares as collateral, retaining voting rights but passing through the economic value of any dividends to the buyer during the pledge. The eventual number of shares delivered will depend on DraftKings’ share price at maturity, with a floor price of $19.20 and a cap price of $40.00 guiding the settlement formula.

Insights

Equity derivatives and insider transactions analyst

Kalish monetizes a large DraftKings stake via a prepaid variable forward.

Director Matthew Kalish has structured a prepaid variable forward sale contract on up to 1,912,236 DraftKings Class A shares. He receives $31,720,935.66 upfront while committing to deliver a variable number of shares after May 18, 2029, depending on the stock price then.

The arrangement pledges the same 1,912,236 shares as collateral. Kalish keeps voting rights during the term but passes dividend economics to the counterparty, so his economic exposure shifts toward a pre-agreed payoff profile. This is categorized as an "other" restructuring transaction rather than an open-market sale.

The share delivery formula uses a $19.20 Floor Level and $40.00 Cap Level as reference prices, which will determine how many shares are ultimately transferred at the Maturity Date. Future disclosures may clarify how this contract interacts with Kalish’s broader holdings and any additional hedging activity.

Insider Trade Summary

1 transaction reported

Mixed 1 txn

Insider Kalish Matthew

Role null

Type	Security	Shares	Price	Value
Other	Forward Sale Contract (obligation to sell)	1,912,236	$0.00	--

Holdings After Transaction: Forward Sale Contract (obligation to sell) — 1,912,236 shares (Direct, null)

Footnotes (1)

1. On May 15, 2026, the Reporting Person entered into a prepaid variable forward sale contract with an unaffiliated third party buyer. The contract obligates the Reporting Person to deliver to the buyer up to an aggregate 1,912,236 shares (the "Base Amount") of the Issuer's Class A Common Stock on a settlement date following May 18, 2029 (the "Maturity Date"). In exchange for assuming this obligation, the Reporting Person will receive a cash payment of $31,720,935.66 on May 18, 2026. The Reporting Person pledged 1,912,236 shares of the Issuer's Class A Common Stock (the "Pledged Shares") to secure his obligations under the contract, and retained voting rights in the Pledged Shares during the term of the pledge, but is obligated to pay to the buyer the economic benefits of dividends during the term of the pledge. The number of shares of the Issuer's Class A Common Stock to be delivered by the Reporting Person to the buyer on the settlement date is to be generally determined as follows: (a) if the closing price of shares of the Issuer's Class A Common Stock on the Maturity Date (the "Settlement Price") is less than $40.00 ("Cap Level") but greater than $19.20 ("Floor Level"), the Reporting Person will deliver a number of shares of the Issuer's Class A Common Stock equal to the Base Amount multiplied by a ratio equal to the Floor Level divided by the Settlement Price; (continued on footnote 3 to this Form 4) (Continued from footnote 2 to this Form 4) (b) if the Settlement Price is equal to or greater than the Cap Level on the Maturity Date, the Reporting Person will deliver a number of shares of the Issuer's Class A Common Stock equal to the Base Amount multiplied by a ratio equal to a fraction with a numerator equal to the sum of (A) the Floor Level and (B) the excess, if any, of the Settlement Price over the Cap Level, and a denominator equal to the Settlement Price; and (c) if the Settlement Price is equal to or less than the Floor Level on the Maturity Date, the Reporting Person will deliver a number of shares of the Issuer's Class A Common Stock equal to the Base Amount.

Key Figures

Base Amount shares: 1,912,236 shares Upfront cash received: $31,720,935.66 Floor Level price: $19.20 +2 more

5 metrics

Base Amount shares 1,912,236 shares Maximum Class A shares deliverable under the forward contract

Upfront cash received $31,720,935.66 Payment to Kalish on May 18, 2026 for entering the contract

Floor Level price $19.20 Lower reference price used in settlement share formula

Cap Level price $40.00 Upper reference price used in settlement share formula

Restructuring shares 1,912,236 shares Shares referenced in derivative restructuring transaction (Code J)

Key Terms

prepaid variable forward sale contract, Base Amount, Floor Level, Cap Level, +1 more

5 terms

prepaid variable forward sale contract financial

"entered into a prepaid variable forward sale contract with an unaffiliated third party buyer"

Base Amount financial

"up to an aggregate 1,912,236 shares (the "Base Amount") of the Issuer's Class A Common Stock"

Floor Level financial

"greater than $19.20 ("Floor Level"), the Reporting Person will deliver a number of shares"

Cap Level financial

"if the closing price ... is less than $40.00 ("Cap Level") but greater than $19.20"

Maturity Date financial

"on a settlement date following May 18, 2029 (the "Maturity Date")"

The maturity date is the specific day when a loan, bond, or investment reaches its full term and the borrower must repay the borrowed amount in full. It is important for investors because it indicates when they will receive their initial money back and can plan their future financial steps accordingly. Think of it as the due date for a loan or the day a gift card or coupon expires.

Form 4 Insider Transactions: What Each Field Means →

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).

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 MASSACHUSETTS 02116

(City) (State) (Zip)

UNITED STATES

(Country)

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
	Officer (give title below)		Other (specify below)

2a. Foreign Trading Symbol

3. Date of Earliest Transaction (Month/Day/Year)
05/15/2026

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

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

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

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

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
Forward Sale Contract (obligation to sell)	(1)(2)(3)	05/15/2026		J/K			1,912,236	(1)(2)(3)	(1)(2)(3)	Class A Common Stock	1,912,236	(1)(2)(3)	1,912,236	D

Explanation of Responses:

1. On May 15, 2026, the Reporting Person entered into a prepaid variable forward sale contract with an unaffiliated third party buyer. The contract obligates the Reporting Person to deliver to the buyer up to an aggregate 1,912,236 shares (the "Base Amount") of the Issuer's Class A Common Stock on a settlement date following May 18, 2029 (the "Maturity Date"). In exchange for assuming this obligation, the Reporting Person will receive a cash payment of $31,720,935.66 on May 18, 2026. The Reporting Person pledged 1,912,236 shares of the Issuer's Class A Common Stock (the "Pledged Shares") to secure his obligations under the contract, and retained voting rights in the Pledged Shares during the term of the pledge, but is obligated to pay to the buyer the economic benefits of dividends during the term of the pledge.

2. The number of shares of the Issuer's Class A Common Stock to be delivered by the Reporting Person to the buyer on the settlement date is to be generally determined as follows: (a) if the closing price of shares of the Issuer's Class A Common Stock on the Maturity Date (the "Settlement Price") is less than $40.00 ("Cap Level") but greater than $19.20 ("Floor Level"), the Reporting Person will deliver a number of shares of the Issuer's Class A Common Stock equal to the Base Amount multiplied by a ratio equal to the Floor Level divided by the Settlement Price; (continued on footnote 3 to this Form 4)

3. (Continued from footnote 2 to this Form 4) (b) if the Settlement Price is equal to or greater than the Cap Level on the Maturity Date, the Reporting Person will deliver a number of shares of the Issuer's Class A Common Stock equal to the Base Amount multiplied by a ratio equal to a fraction with a numerator equal to the sum of (A) the Floor Level and (B) the excess, if any, of the Settlement Price over the Cap Level, and a denominator equal to the Settlement Price; and (c) if the Settlement Price is equal to or less than the Floor Level on the Maturity Date, the Reporting Person will deliver a number of shares of the Issuer's Class A Common Stock equal to the Base Amount.

Remarks:

	/s/ Faisal Hasan, attorney-in-fact	05/15/2026
	** 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.
* Form 4: SEC 1474 (03-26)

FAQ

What did DraftKings (DKNG) director Matthew Kalish report in this Form 4?

Matthew Kalish entered a prepaid variable forward sale contract on up to 1,912,236 DraftKings Class A shares. He pledged these shares as collateral and agreed to deliver a variable number after May 18, 2029, instead of making an immediate open-market sale.

How much cash does Matthew Kalish receive under the DraftKings (DKNG) forward contract?

Kalish will receive a cash payment of $31,720,935.66 on May 18, 2026. This upfront amount compensates him for obligating himself to deliver up to 1,912,236 DraftKings Class A shares at a future settlement date after May 18, 2029.

How many DraftKings (DKNG) shares are covered by Kalish’s prepaid variable forward?

The contract covers a Base Amount of up to 1,912,236 DraftKings Class A shares. Kalish pledged the same number of shares as collateral and will deliver a variable portion of this amount based on the stock price on the future Maturity Date.

Does Matthew Kalish keep voting rights on the DraftKings (DKNG) shares in this contract?

Yes, Kalish retained voting rights in the 1,912,236 pledged DraftKings Class A shares for the contract’s term. However, he must pass through to the buyer the economic benefits of any dividends paid on these shares while they are pledged.

How is the number of DraftKings (DKNG) shares delivered under the forward contract determined?

The delivered share count depends on the Settlement Price on the Maturity Date. A Floor Level of $19.20 and Cap Level of $40.00 define formulas that adjust how many of the 1,912,236 Base Amount shares Kalish must ultimately transfer to the buyer.

Is Kalish’s DraftKings (DKNG) forward contract an open-market sale of shares?

No, the Form 4 categorizes this as an “other” derivative restructuring transaction. Kalish receives $31,720,935.66 upfront and commits to deliver a variable number of shares later, rather than selling shares directly on the open market now.