OCSL Oaktree Specialty Lending Corp Insider Trading

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 Gero buys 2,000 shares of OCSL at $10.78; stock now at $11.26, down 28.6% from 52-week high

Director Deborah Ann Gero purchased 2,000 shares at $10.78 on 2026-03-16, increasing her holdings by 8.9% to 24,411 shares. The purchase occurred near the 52-week low ($10.78), with the stock currently trading at $11.26—still 28.6% below its 52-week high of $15.78 and down 12.2% over 90 days. Gero's prior buy at OCSL on 2025-06-30 resulted in a negative 90-day return (-4.7%), and her cross-ticker track record shows zero wins in limited transaction history (0.00% 90-day win rate). The timing coincides with price weakness rather than recovery momentum.

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 Deborah Ann Gero buys 2,500 shares of OCSL at $13.70; holds 22,411 shares post-transaction.

Director Deborah Ann Gero purchased 2,500 shares at $13.70 on 2025-06-30, increasing her holdings to 22,411 shares—a 12.6% net increase from her prior position of 19,911 shares. The purchase occurred as the stock traded 26.9% below its 52-week high of $18.82 and had declined 10.2% over the prior 90 days. However, context for interpreting this buy is limited: the company reported net income of -$36,249,000.00 and has a P/E ratio of 137.50, indicating deep losses. Without visibility into whether this purchase was discretionary or scheduled under a trading plan, and without prior trading history to establish Gero's typical behavior, the isolated transaction provides insufficient signal regarding her conviction or the stock's outlook. The acquisition warrants attention primarily as a data point for tracking this director's ongoing commitment to the company.

Panossian buys 8,000 OCSL shares at $14.13; 3-insider cluster buy in 14 days despite -$36.2M net income

Panossian Armen purchased 8,000 shares of Oaktree Specialty Lending Corp at $14.13, representing a 62.6% increase in his holdings. This transaction occurs within a cluster pattern: 2 other insiders also bought within the past 14 days. The company reported net income of -$36,249,000.00 and trades at 144.50 P/E, with the stock currently 26.8% below its 52-week high. The coordinated buying by multiple insiders during a period of negative earnings and depressed valuation relative to recent highs warrants investor attention as a potential signal of insider perspective on intrinsic value.

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 Jacobson purchases 14,910 shares of OCSL at $13.41; holdings rise 26.3% to 71,667 shares amid negative earnings environment.

Jacobson Craig A, as a Director, acquired 14,910 shares at $13.41 on 2025-05-06, representing a 26.3% increase in his holdings. The purchase occurs in a context of material headwinds: the company reported net income of $-36,249,000.00, and the current stock price of $13.34 sits 32.5% below the 52-week high, having declined 14.2% over the past 90 days. The timing and magnitude of the buy—growing holdings by more than a quarter—warrants attention as a data point on insider perspective, particularly given the recent downward price momentum and negative earnings backdrop. Investors should track whether this transaction signals management confidence in recovery or represents an isolated portfolio decision.

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.

Pendo Mathew (President) bought 6,260 shares of OCSL at $15.92; 2 other insiders also bought within 14 days

Pendo Mathew, as President of Oaktree Specialty Lending Corp, purchased 6,260 shares at $15.92, expanding his holdings by 13.5% to 52,596 shares total. This transaction carries elevated significance due to a cluster pattern: 2 other insiders also initiated buys within the past 14 days, indicating coordinated accumulation at a price 21.0% below the 52-week high of $20.15. The concurrent buying by multiple executives at this price level suggests internal appetite for ownership at valuations near recent lows, though the company maintains a P/E of 24.12 against $7.2M in net income. The clustering warrants monitoring to determine whether this reflects opportunistic accumulation or a broader management assessment of intrinsic value.

Co-CIO Khanna Raghav bought 6,000 shares of OCSL at $15.95; cluster of 2 other insiders also purchased within 14 days

Raghav's purchase of 6,000 shares at $15.95 on 2025-02-24 represents his first holding position in OCSL, and arrives as part of a cluster pattern with 2 other insiders buying within the past 14 days. The stock is currently trading at $15.92, only marginally below the transaction price, and remains -21.0% from its 52-week high of $20.15. The concurrent insider activity suggests aligned interest at current valuation levels. With OCSL trading at a P/E of 24.12 and a market cap of $1,309,345,478.48, this filing warrants examination of whether the cluster pattern reflects substantive capital allocation or routine portfolio positioning.