KAPLAN STEPHEN A

Director Kaplan buys 10,000 TSQ shares at $6.92; stock now $6.82, down 37.7% from 52-week high.

Stephen A. Kaplan, a director of Townsquare Media, purchased 10,000 shares at $6.92 on 2025-08-22, expanding his holdings to 208.6K shares. This is his second consecutive buy in August (following a purchase on 2025-08-11), and his third open-market purchase overall at this ticker. However, his prior buy at TSQ on 2024-09-20 at a similar price level delivered a 90-day return of -7.2%, and his cross-ticker track record shows 0% win rate across 2 prior buys with an average 90-day return of -7.2%. The current price of $6.82 is now 37.7% below the 52-week high of $10.94, suggesting the stock has deteriorated significantly since his prior entry points. Townsquare's fundamentals are concerning: the company was unprofitable over its most recent full fiscal year, annual revenue growth is negative at -0.7%, and while the latest quarter showed $115.4M revenue, net income was only $1.6M. The P/E of 3.61 is suppressed by minimal earnings, not valuation attractiveness. Kaplan's repeated purchases into a declining stock with deteriorating fundamentals and a pattern of poor subsequent returns presents a contrarian signal rather than a vote of confidence.

Director Stephen A Kaplan purchases 46,509 shares of TSQ at $6.77; position grows 30.6% to 198,618 shares

Director Stephen A Kaplan purchased 46,509 shares of Townsquare Media at $6.77 on 2025-08-11, increasing his holdings by 30.6% from 152,109 to 198,618 shares. The purchase occurs in a stock trading 39.1% below its 52-week high and down 16.5% over the prior 30 days, but Kaplan's historical track record at this ticker offers limited confidence: his prior buy at TSQ on 2024-09-20 resulted in a -7.2% return over 90 days, and his cross-ticker open-market buying history shows an average 90-day return of -7.2% with a 0.00% win rate across 1 prior buy. The company faces structural headwinds—annual revenue declined 0.7% year-over-year, it posted negative full-year net income despite a latest-quarter profit of $1.6M, and the stock's severely depressed valuation (P/E of 3.69) reflects fundamental concerns that a director purchase alone does not resolve.

Director Kaplan buys 50,000 TSQ shares at $10.41; stock now at $10.29, company unprofitable with -$49.2M net income.

Director Stephen A Kaplan purchased 50,000 shares of Townsquare Media at $10.41 on 2024-09-20, increasing his holdings from 87,808 to 137,808 shares—a 56.9% increase in position size. The timing comes as the stock has declined 21.5% from its 52-week high of $13.11 and currently trades at $10.29, near the transaction price. Notably, the company reported a net loss of $-49.2M in its most recent fiscal year, with annual revenue declining 1.9% year-over-year. This purchase by a director into a financially distressed company with negative earnings and declining growth warrants examination of the company's underlying business trajectory and restructuring efforts.