Matthew Kalish - Mar 1, 2025 Form 4 Insider Report for DraftKings Inc. (DKNG)

Signature
/s/ Faisal Hasan, attorney-in-fact
Stock symbol
DKNG
Transactions as of
Mar 1, 2025
Transactions value $
-$16,915,207
Form type
4
Date filed
3/4/2025, 09:49 PM
Previous filing
Feb 24, 2025

Transactions Table

Type Sym Class Transaction Value $ Shares Change % * Price $ Shares After Date Ownership Footnotes
transaction DKNG Class A Common Stock Options Exercise +22.1K +0.54% 4.14M Mar 1, 2025 Direct F1
transaction DKNG Class A Common Stock Tax liability -$468K -10.7K -0.26% $43.86 4.13M Mar 1, 2025 Direct
transaction DKNG Class A Common Stock Options Exercise +9.65K +0.23% 4.14M Mar 1, 2025 Direct F2
transaction DKNG Class A Common Stock Tax liability -$205K -4.67K -0.11% $43.86 4.14M Mar 1, 2025 Direct
transaction DKNG Class A Common Stock Options Exercise $603K +158K +3.81% $3.82 4.3M Mar 3, 2025 Direct F3
transaction DKNG Class A Common Stock Options Exercise $172K +52.2K +1.21% $3.29 4.35M Mar 3, 2025 Direct F3
transaction DKNG Class A Common Stock Sale -$2.11M -50.5K -1.16% $41.84 4.3M Mar 3, 2025 Direct F4, F5
transaction DKNG Class A Common Stock Sale -$1.86M -43.1K -1% $43.10 4.25M Mar 3, 2025 Direct F4, F6
transaction DKNG Class A Common Stock Sale -$5.12M -116K -2.73% $44.05 4.14M Mar 3, 2025 Direct F4, F7
transaction DKNG Class A Common Stock Options Exercise +3.25K +0.08% 4.14M Mar 3, 2025 Direct F8
transaction DKNG Class A Common Stock Tax liability -$37.4K -791 -0.02% $47.29 4.14M Mar 3, 2025 Direct
transaction DKNG Class A Common Stock Options Exercise +40 +0.02% 196K Mar 3, 2025 Held by Kalish Family 2020 Irrevocable Trusts F9
transaction DKNG Class A Common Stock Tax liability -$473 -10 -0.01% $47.29 196K Mar 3, 2025 Held by Kalish Family 2020 Irrevocable Trusts
transaction DKNG Class A Common Stock Options Exercise +3.88K 3.88K Mar 3, 2025 Held by Matthew P. Kalish 2020 Trust F10
transaction DKNG Class A Common Stock Tax liability -$44.7K -945 -24.34% $47.29 2.94K Mar 3, 2025 Held by Matthew P. Kalish 2020 Trust
transaction DKNG Class A Common Stock Options Exercise $625K +190K +4.59% $3.29 4.33M Mar 4, 2025 Direct F3
transaction DKNG Class A Common Stock Options Exercise $66K +20.1K +0.46% $3.29 4.35M Mar 4, 2025 Direct F3
transaction DKNG Class A Common Stock Sale -$3.69M -92.7K -2.13% $39.77 4.26M Mar 4, 2025 Direct F4, F11
transaction DKNG Class A Common Stock Sale -$2.07M -50.5K -1.19% $40.91 4.21M Mar 4, 2025 Direct F4, F12
transaction DKNG Class A Common Stock Sale -$2.72M -65.6K -1.56% $41.53 4.14M Mar 4, 2025 Direct F4, F13
transaction DKNG Class A Common Stock Sale -$51.9K -1.23K -0.03% $42.28 4.14M Mar 4, 2025 Direct F4, F14

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 -22.1K -11.11% $0.00 176K Mar 1, 2025 Class A Common Stock 22.1K Direct F1, F15
transaction DKNG Restricted Stock Units Options Exercise $0 -9.65K -7.69% $0.00 116K Mar 1, 2025 Class A Common Stock 9.65K Direct F2, F16
transaction DKNG Stock Option Options Exercise $0 -158K -100% $0.00 0 Mar 3, 2025 Class A Common Stock 158K $3.82 Direct F17
transaction DKNG Stock Option Options Exercise $0 -52.2K -21.55% $0.00 190K Mar 3, 2025 Class A Common Stock 52.2K $3.29 Direct F18
transaction DKNG Warrant for Common Stock Options Exercise $0 -3.25K -100% $0.00 0 Mar 3, 2025 Class A Common Stock 3.25K $11.50 Direct F8
transaction DKNG Warrant for Common Stock Options Exercise $0 -40 -100% $0.00 0 Mar 3, 2025 Class A Common Stock 40 $11.50 Held by Kalish Family 2020 Irrevocable Trusts F9
transaction DKNG Warrant for Common Stock Options Exercise $0 -3.88K -100% $0.00 0 Mar 3, 2025 Class A Common Stock 3.88K $11.50 Held by Matthew P. Kalish 2020 Trust F10
transaction DKNG Stock Option Options Exercise $0 -190K -100% $0.00 0 Mar 4, 2025 Class A Common Stock 190K $3.29 Direct F18
transaction DKNG Stock Option Options Exercise $0 -20.1K -1.77% $0.00 1.11M Mar 4, 2025 Class A Common Stock 20.1K $3.29 Direct F19
* 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 22,059 shares of Class A Common Stock underlying the RSUs listed in Table II, and 10,666 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 No shares of Class A Common Stock were transferred or sold upon the vesting of the RSUs other than to the Issuer to satisfy withholding taxes. The Reporting Person received the net of the 9,649 shares of Class A Common Stock underlying the RSUs listed in Table II, and 4,666 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.
F3 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 withholdings in cash.
F4 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.
F5 The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $41.53 to $42.46, 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 Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in footnotes 5, 6, 7, 11, 12, 13 and 14 to this Form 4.
F6 The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions ranging from $42.63 to $43.61, inclusive. See the last sentence of footnote 5 to this Form 4 above.
F7 The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions ranging from $43.63 to $44.48, inclusive. See the last sentence of footnote 5 to this Form 4 above.
F8 The Reporting Person acquired shares of Class A Common Stock of the Issuer after the exchange of warrants for common stock for $11.50 per share on a cashless basis in a private transaction entered into between the Reporting Person and the Issuer. The Reporting Person received the net of 3,251 shares of Class A Common Stock underlying the warrants for common stock listed in Table II, and 791 shares of Class A Common Stock withheld by the issuer in consideration of the exercise of the warrants for common stock. Each warrant to purchase Class A Common Stock is exercisable for one share of Class A Common Stock at an exercise price of $11.50 per share.
F9 The Reporting Person acquired shares of Class A Common Stock of the Issuer after the exchange of warrants for common stock for $11.50 per share on a cashless basis in a private transaction entered into between the Reporting Person and the Issuer. The Reporting Person received the net of 40 shares of Class A Common Stock underlying the warrants for common stock listed in Table II, and 10 shares of Class A Common Stock withheld by the issuer in consideration of the exercise of the warrants for common stock. Each warrant to purchase Class A Common Stock is exercisable for one share of Class A Common Stock at an exercise price of $11.50 per share.
F10 The Reporting Person acquired shares of Class A Common Stock of the Issuer after the exchange of warrants for common stock for $11.50 per share on a cashless basis in a private transaction entered into between the Reporting Person and the Issuer. The Reporting Person received the net of 3,883 shares of Class A Common Stock underlying the warrants for common stock listed in Table II, and 945 shares of Class A Common Stock withheld by the issuer in consideration of the exercise of the warrants for common stock. Each warrant to purchase Class A Common Stock is exercisable for one share of Class A Common Stock at an exercise price of $11.50 per share.
F11 The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions ranging from $39.27 to $40.26, inclusive. See the last sentence of footnote 5 to this Form 4 above.
F12 The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions ranging from $40.27 to $41.26, inclusive. See the last sentence of footnote 5 to this Form 4 above.
F13 The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions ranging from $41.27 to $42.15, inclusive. See the last sentence of footnote 5 to this Form 4 above.
F14 The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions ranging from $42.28 to $42.37, inclusive. See the last sentence of footnote 5 to this Form 4 above.
F15 On February 13, 2023, the Reporting Person was granted 352,941 RSUs vesting quarterly over four (4) years from March 1, 2023.
F16 On February 12, 2024, the Reporting Person was granted 154,392 RSUs vesting quarterly over four (4) years from March 1, 2024.
F17 These stock options were granted on May 3, 2017. As of the date hereof, all of such remaining stock options have vested.
F18 These stock options were granted on April 18, 2018. As of the date hereof, all of such remaining stock options have vested.
F19 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