CALDWELL PHYLLIS R

Director Phyllis R Caldwell buys 2,500 shares of OCSL at $10.77; stock down 28.6% from 52-week high.

Director Caldwell purchased 2,500 shares at $10.77, increasing her holdings by 11.9% to 23,500 shares post-transaction. The stock has declined 28.6% from its 52-week high of $15.78 and is currently trading at $11.26, only $0.49 above the purchase price. Her prior trades at OCSL show mixed timing: 3 of 5 prior buys were well-timed at the 90-day mark, with returns ranging from -10.9% to +7.5% over 90 days. The company's current valuation metrics show a P/E of 30.43 against $5.6M net income and a market cap of $991.8M, suggesting relatively elevated valuations despite recent price weakness. This purchase occurs within a context of elevated valuations and recent price deterioration, with her historical trading pattern at this ticker showing inconsistent predictive power.

Director Caldwell purchases 3,000 shares at $13.19 blended average; stock down 19.9% from 52-week high, but 5 prior OCSL buys show 0% timing success at 90-day mark.

Phyllis R. Caldwell, Director, executed 3 separate purchases totaling 3,000 shares for $39,576.45 on 2025-09-15, raising her holdings 16.7% from 18,000 to 21,000 shares. The stock is trading at $13.32, down 19.9% from its 52-week high of $16.62, and her blended average purchase price of $13.19 suggests entry near recent lows. However, her same-ticker trade history at OCSL presents a cautionary pattern: all 5 prior buys at this stock generated negative or flat 90-day returns, with a 0% win rate at the 90-day horizon despite occasional 30-day rallies. The cross-ticker track record reinforces this pattern with an average 90-day return of -4.2% across 8 open-market buys elsewhere. While a depressed valuation relative to 52-week levels may have motivated this purchase, the director's historical timing outcomes at this specific ticker offer limited evidence of predictive accuracy for subsequent price appreciation.

Director Phyllis R Caldwell buys 2,000 OCSL shares at $13.32; stock down -30.8% from 52-week high, insider's prior OCSL buys showed 0 wins at 90-day mark.

Phyllis R Caldwell, a director, purchased 2,000 shares of Oaktree Specialty Lending Corp at $13.32 on 2025-05-07, increasing holdings by 12.5% to 18,000 shares. The current price of $13.66 reflects a -30.8% decline from the 52-week high of $19.75, placing the purchase in a depressed price environment. However, her prior trade history at OCSL offers limited reassurance: across 5 prior trades at this ticker, all were buys, and the timing pattern shows 0 of 4 prior buys generated positive 90-day returns, with an average 90-day outcome of -5.2% at OCSL. The company is also trading at a P/E of 136.60 with negative net income of $-36,249,000.00, suggesting fundamental stress that may warrant investor scrutiny independent of this insider's transaction pattern.

Director Phyllis R Caldwell buys 2,500 shares of OCSL at $15.83; cluster pattern with 2 other insiders buying in past 14 days.

Director Caldwell purchased 2,500 shares at $15.83 on 2025-02-25, increasing her holdings from 13,500 to 16,000 shares (+18.5% increase). The transaction occurs within a cluster: 2 other insiders also bought within the past 14 days, suggesting coordinated board or management interest. However, her own prior trades at OCSL show a poor timing pattern—0 of 5 prior buys resulted in positive 90-day returns, with all five trades posting 90-day declines ranging from -1.7% to -5.2%. The stock is currently 21.0% below its 52-week high at $15.92, and her cross-ticker track record shows a 0.00% 90-day win rate across 6 prior buys. The weak historical timing pattern and depressed price relative to the 52-week range should be weighed against the multi-insider cluster buy signal.

Director Phyllis R Caldwell bought 1,000 shares at $16.01 on 2024-09-20; stock now -25.6% from 52-week high and -5.9% over 30 days.

Director Phyllis R Caldwell executed 3 separate purchases totaling 1,000 shares for $16,009.49 on 2024-09-20, raising her holdings to 13,500 shares (an 8.0% increase). The purchases occurred at $16.01 blended average, near the current price of $16.02, but the stock has declined -25.6% from its 52-week high of $21.54 and fallen -5.9% over the past 30 days. Her prior same-ticker trades at OCSL show mixed timing: two August 2024 buys posted modest short-term gains (+0.8% and +0.7% at 30 days), while a February 2024 buy yielded -1.8% and -3.7% returns at the 30- and 90-day marks respectively. Across her cross-ticker trading history, she has achieved a 0.00% 90-day win rate on 3 prior buys. The transaction reflects continued accumulation at a depressed price, though the insider's broader pattern offers limited evidence of reliable buy timing.

Director Phyllis R Caldwell purchased 1,334 shares for $21,725.86 at OCSL; stock is -23.4% from 52-week high, -10.9% over 30 days.

Director Caldwell made two separate purchases totaling 1,334 shares on 2024-08-13 at a blended average price of $16.29, bringing her holdings to 12,500 shares post-transaction. The transaction occurred when Oaktree Specialty Lending Corp (OCSL) is down 23.4% from its 52-week high of $21.54 and has declined 10.9% over the prior 30 days, suggesting the purchase followed recent weakness in the stock price. However, Caldwell's prior buy at this ticker on 2024-02-12 produced a 90-day return of -3.7%, indicating a pattern where her past open-market purchases at OCSL have not preceded near-term recovery. The current stock price of $16.49 is only marginally higher than her transaction prices of $16.28 and $16.29, leaving limited upside realized to date.