A Form 4 is filed within two business days of a company insider — an officer, a director, or a holder of more than ten percent of the stock — changing their position in the shares. All 13 filings in this group are Form 4s for iHeartMedia, Inc.
The difficulty with reading these filings as a group is that a single form type covers transactions that mean entirely different things. An executive spending their own money to buy stock and an executive having shares withheld to pay tax on a vesting grant both appear as a Form 4. Every filing below is therefore tagged with the nature of the underlying transaction, taken from the transaction code reported on the form itself.
Across the 13 insider filings shown, the breakdown is 6 compensation award, 2 option exercise, 2 open-market purchase, 2 tax withholding and 1 gift. 2 of them involved a discretionary open-market trade; the rest are compensation and administrative mechanics.
Form 4
Gift
Tax / Compensation Filing
2026-07-31
IHRT insider Form 4 filed for equity award, exercise, or tax withholding
MILLARD ROBERT B (Director) filed a Form 4 covering compensation-related activity such as stock awards, option exercises, conversions, or tax withholding. These filings are usually neutral.
Shares were transferred as a gift, typically for estate or charitable planning. No sale into the market took place.
Transactions reported on this filing
| Code |
Nature |
Shares |
Price |
Value |
G |
Gift
|
137,734 |
— |
— |
G |
Gift
|
137,734 |
— |
— |
Filing: Form 4 (Insider Transaction)
Insider: MILLARD ROBERT B (Director)
Shares: 275,468
Form 4
Compensation award
Tax / Compensation Filing
2026-06-08
IHRT insider Form 4 filed for equity award, exercise, or tax withholding
SIVARAMAKRISHNAN KAMAKSHI (Director) filed a Form 4 covering compensation-related activity such as stock awards, option exercises, conversions, or tax withholding. These filings are usually neutral.
Shares were granted as compensation rather than purchased. No cash changed hands, so the filing reflects a pay decision by the company, not a judgement about the price.
Transactions reported on this filing
| Code |
Nature |
Shares |
Price |
Value |
A |
Compensation award
|
35,629 |
— |
— |
Filing: Form 4 (Insider Transaction)
Insider: SIVARAMAKRISHNAN KAMAKSHI (Director)
Shares: 35,629
Form 4
Compensation award
Tax / Compensation Filing
2026-06-05
IHRT insider Form 4 filed for equity award, exercise, or tax withholding
Monteagudo Graciela (Director) filed a Form 4 covering compensation-related activity such as stock awards, option exercises, conversions, or tax withholding. These filings are usually neutral.
Shares were granted as compensation rather than purchased. No cash changed hands, so the filing reflects a pay decision by the company, not a judgement about the price.
Transactions reported on this filing
| Code |
Nature |
Shares |
Price |
Value |
A |
Compensation award
|
35,629 |
— |
— |
Filing: Form 4 (Insider Transaction)
Insider: Monteagudo Graciela (Director)
Shares: 35,629
Form 4
Compensation award
Tax / Compensation Filing
2026-06-05
IHRT insider Form 4 filed for equity award, exercise, or tax withholding
Englebardt Samuel Eli (Director) filed a Form 4 covering compensation-related activity such as stock awards, option exercises, conversions, or tax withholding. These filings are usually neutral.
Shares were granted as compensation rather than purchased. No cash changed hands, so the filing reflects a pay decision by the company, not a judgement about the price.
Transactions reported on this filing
| Code |
Nature |
Shares |
Price |
Value |
A |
Compensation award
|
35,629 |
$4.21 |
$150.0K |
A |
Compensation award
|
35,629 |
— |
— |
Filing: Form 4 (Insider Transaction)
Insider: Englebardt Samuel Eli (Director)
Shares: 71,258
Form 4
Compensation award
Tax / Compensation Filing
2026-06-05
IHRT insider Form 4 filed for equity award, exercise, or tax withholding
MILLARD ROBERT B (Director) filed a Form 4 covering compensation-related activity such as stock awards, option exercises, conversions, or tax withholding. These filings are usually neutral.
Shares were granted as compensation rather than purchased. No cash changed hands, so the filing reflects a pay decision by the company, not a judgement about the price.
Transactions reported on this filing
| Code |
Nature |
Shares |
Price |
Value |
A |
Compensation award
|
35,629 |
$4.21 |
$150.0K |
A |
Compensation award
|
35,629 |
— |
— |
Filing: Form 4 (Insider Transaction)
Insider: MILLARD ROBERT B (Director)
Shares: 71,258
Form 4
Compensation award
Tax / Compensation Filing
2026-06-05
IHRT insider Form 4 filed for equity award, exercise, or tax withholding
Rasulo James A (Director) filed a Form 4 covering compensation-related activity such as stock awards, option exercises, conversions, or tax withholding. These filings are usually neutral.
Shares were granted as compensation rather than purchased. No cash changed hands, so the filing reflects a pay decision by the company, not a judgement about the price.
Transactions reported on this filing
| Code |
Nature |
Shares |
Price |
Value |
A |
Compensation award
|
35,629 |
— |
— |
Filing: Form 4 (Insider Transaction)
Insider: Rasulo James A (Director)
Shares: 35,629
Form 4
Compensation award
Tax / Compensation Filing
2026-06-05
IHRT insider Form 4 filed for equity award, exercise, or tax withholding
MILLS CHERYL D (Director) filed a Form 4 covering compensation-related activity such as stock awards, option exercises, conversions, or tax withholding. These filings are usually neutral.
Shares were granted as compensation rather than purchased. No cash changed hands, so the filing reflects a pay decision by the company, not a judgement about the price.
Transactions reported on this filing
| Code |
Nature |
Shares |
Price |
Value |
A |
Compensation award
|
35,629 |
— |
— |
Filing: Form 4 (Insider Transaction)
Insider: MILLS CHERYL D (Director)
Shares: 35,629
Form 4
Option exercise
Tax / Compensation Filing
2026-05-20
IHRT insider Form 4 filed for equity award, exercise, or tax withholding
BRESSLER RICHARD J (Director, President and COO) filed a Form 4 covering compensation-related activity such as stock awards, option exercises, conversions, or tax withholding. These filings are usually neutral.
The insider converted options into shares. The exercise price was fixed when the options were granted, so the timing usually tracks an expiry schedule.
Transactions reported on this filing
| Code |
Nature |
Shares |
Price |
Value |
M |
Option exercise
|
528,768 |
— |
— |
F |
Tax withholding on vested shares
|
226,630 |
$5.18 |
$1.17M |
D |
Disposition to issuer
|
302,138 |
$5.18 |
$1.57M |
F |
Tax withholding on vested shares
|
554,965 |
$5.18 |
$2.87M |
M |
Option exercise
derivative · Restricted Stock Units
|
528,768 |
— |
— |
Filing: Form 4 (Insider Transaction)
Insider: BRESSLER RICHARD J (Director, President and COO)
Shares: 1,612,501
Form 4
Option exercise
Tax / Compensation Filing
2026-05-20
IHRT insider Form 4 filed for equity award, exercise, or tax withholding
PITTMAN ROBERT W (Director, Chairman and CEO) filed a Form 4 covering compensation-related activity such as stock awards, option exercises, conversions, or tax withholding. These filings are usually neutral.
The insider converted options into shares. The exercise price was fixed when the options were granted, so the timing usually tracks an expiry schedule.
Transactions reported on this filing
| Code |
Nature |
Shares |
Price |
Value |
M |
Option exercise
|
528,768 |
— |
— |
F |
Tax withholding on vested shares
|
226,630 |
$5.18 |
$1.17M |
D |
Disposition to issuer
|
302,138 |
$5.18 |
$1.57M |
F |
Tax withholding on vested shares
|
554,965 |
$5.18 |
$2.87M |
M |
Option exercise
derivative · Restricted Stock Units
|
528,768 |
— |
— |
Filing: Form 4 (Insider Transaction)
Insider: PITTMAN ROBERT W (Director, Chairman and CEO)
Shares: 1,612,501
Form 4
Tax withholding
Tax / Compensation Filing
2026-05-20
IHRT insider Form 4 filed for equity award, exercise, or tax withholding
MCGUINNESS MICHAEL B (CFO) filed a Form 4 covering compensation-related activity such as stock awards, option exercises, conversions, or tax withholding. These filings are usually neutral.
Shares were withheld by the company to settle tax due when equity vested. This is an automatic administrative step and not a decision to sell.
Transactions reported on this filing
| Code |
Nature |
Shares |
Price |
Value |
F |
Tax withholding on vested shares
|
115,678 |
$5.18 |
$599.2K |
Filing: Form 4 (Insider Transaction)
Insider: MCGUINNESS MICHAEL B (CFO)
Shares: 115,678
Form 4
Tax withholding
Tax / Compensation Filing
2026-04-29
IHRT insider Form 4 filed for equity award, exercise, or tax withholding
Hillman David (SEE BELOW) filed a Form 4 covering compensation-related activity such as stock awards, option exercises, conversions, or tax withholding. These filings are usually neutral.
Shares were withheld by the company to settle tax due when equity vested. This is an automatic administrative step and not a decision to sell.
Transactions reported on this filing
| Code |
Nature |
Shares |
Price |
Value |
F |
Tax withholding on vested shares
|
55,300 |
$5.34 |
$295.3K |
Filing: Form 4 (Insider Transaction)
Insider: Hillman David (SEE BELOW)
Shares: 55,300
Form 4
Open-market purchase
Insider Buying
2026-03-09
IHRT insider PITTMAN ROBERT W (Director, Chairman and CEO) bought 16,349 shares (~$48.5K)
PITTMAN ROBERT W, listed as Director, Chairman and CEO at iHeartMedia, Inc., reported an open-market purchase of 16,349 IHRT shares in a Form 4 filing. Insider buying is often treated as a bullish signal because company insiders are committing their own capital.
The insider bought shares on the open market with their own money. This is the only Form 4 category that requires a discretionary cash outlay at the prevailing price.
Transactions reported on this filing
| Code |
Nature |
Shares |
Price |
Value |
P |
Open-market purchase
|
16,349 |
$2.97 |
$48.5K |
Filing: Form 4 (Insider Transaction)
Insider: PITTMAN ROBERT W (Director, Chairman and CEO)
Shares: 16,349
Est. Value: $48.5K
Form 4
Open-market purchase
Insider Buying
2026-03-05
IHRT insider PITTMAN ROBERT W (Director, Chairman and CEO) bought 32,468 shares (~$105.6K)
PITTMAN ROBERT W, listed as Director, Chairman and CEO at iHeartMedia, Inc., reported an open-market purchase of 32,468 IHRT shares in a Form 4 filing. Insider buying is often treated as a bullish signal because company insiders are committing their own capital.
The insider bought shares on the open market with their own money. This is the only Form 4 category that requires a discretionary cash outlay at the prevailing price.
Transactions reported on this filing
| Code |
Nature |
Shares |
Price |
Value |
P |
Open-market purchase
|
32,468 |
$3.25 |
$105.6K |
Filing: Form 4 (Insider Transaction)
Insider: PITTMAN ROBERT W (Director, Chairman and CEO)
Shares: 32,468
Est. Value: $105.6K