Matthew Kalish - 09 Aug 2025 Form 4 Insider Report for DraftKings Inc. (DKNG)

Role
President - DraftKings, North America, Director
Signature
/s/ Faisal Hasan, attorney-in-fact
Issuer symbol
DKNG
Transactions as of
09 Aug 2025
Net transactions value
-$17,176,941
Form type
4
Filing time
12 Aug 2025, 21:52:02 UTC
Previous filing
03 Jun 2025
Next filing
03 Sep 2025
SEC
View on sec.gov

Reporting Owners (1)

Name Relationship Address Signature Signature date CIK
Kalish Matthew President - DraftKings, North America, Director C/O DRAFTKINGS INC., 222 BERKELEY STREET, 5TH FLOOR, BOSTON /s/ Faisal Hasan, attorney-in-fact 12 Aug 2025 0001810190

Transactions Table

Type Sym Class Transaction Value $ Shares Change % * Price $ Shares After Date Ownership Footnotes
transaction DKNG Class A Common Stock Options Exercise +28,309 +0.68% 4,203,921 09 Aug 2025 Direct F1
transaction DKNG Class A Common Stock Tax liability $586,941 -13,688 -0.33% $42.88 4,190,233 09 Aug 2025 Direct
transaction DKNG Class A Common Stock Options Exercise $690,900 +210,000 +5% $3.29 4,400,233 11 Aug 2025 Direct F2
transaction DKNG Class A Common Stock Sale $8,962,800 -210,000 -4.8% $42.68 4,190,233 11 Aug 2025 Direct F3, F4
transaction DKNG Class A Common Stock Options Exercise $690,900 +210,000 +5% $3.29 4,400,233 12 Aug 2025 Direct F2
transaction DKNG Class A Common Stock Sale $9,009,000 -210,000 -4.8% $42.90 4,190,233 12 Aug 2025 Direct F3, F5
holding DKNG Class A Common Stock 196,309 09 Aug 2025 Held by Kalish Family 2020 Irrevocable Trusts
holding DKNG Class A Common Stock 2,938 09 Aug 2025 Held by Matthew P. Kalish 2020 Trust

Derivative Securities (e.g., puts, calls, warrants, options, convertible securities)

Type Sym Class Transaction Value $ Shares Change % * Price $ Shares After Date Underlying Class Amount Exercise Price Ownership Footnotes
transaction DKNG Restricted Stock Units Options Exercise $0 -28,309 -33% $0.000000 56,617 09 Aug 2025 Class A Common Stock 28,309 Direct F1, F6
transaction DKNG Stock option Options Exercise $0 -210,000 -30% $0.000000 483,488 11 Aug 2025 Class A Common Stock 210,000 $3.29 Direct F7
transaction DKNG Stock option Options Exercise $0 -210,000 -43% $0.000000 273,488 12 Aug 2025 Class A Common Stock 210,000 $3.29 Direct F7
* An asterisk sign (*) next to the price indicates that the price is likely invalid.

Buy Plan / Sale Plan: These are also open market purchases/sales of shares, but in this case the transaction is part of a trading plan. Rule 10b5-1 allows insiders to setup a trading plan to buy/sell stocks over a certain period of time. Since the purchases/sales are predetermined, this protects the insiders from violating insider trading law.

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).

Explanation of Responses:

Id Content
F1 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.
F2 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.
F3 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.
F4 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.
F5 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.
F6 On February 9, 2022, the Reporting Person was granted 452,940 RSUs vesting quarterly over four (4) years.
F7 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