GOF GUGGENHEIM STRATEGIC OPPORTUNITIES FUND Insider Trading

CEO Brian E. Binder purchases 4,704 shares of GOF for $50,000.00 at $10.63; stock down 30.3% from 52-week high

Brian E. Binder, President and CEO, executed 3 purchases totaling 4,704 shares for $50,000.00 at a blended average price of $10.63 on 2026-06-23. The current price of $10.60 is -30.3% from the 52-week high of $15.20, and the stock has declined -4.4% over the past 30 days and -3.0% over 90 days. As an insider officer with direct responsibility for fund direction, Binder's acquisition of a new position (moving from 0 to 4,704 shares post-transaction) represents a material commitment by management at a depressed price level relative to recent trading history.

Director of Guggenheim Strategic Opportunities Fund purchases shares in open market amid recent pullback

Thomas F Lydon Jr, a director of GOF, purchased a meaningful stake in the fund through an open-market transaction, deploying nearly $100,000 at current market levels. The purchase comes after a significant pullback from recent highs, suggesting Lydon sees value at these depressed price points despite the recent weakness. Director buying—particularly in a closed-end fund focused on strategic opportunities—typically reflects confidence in underlying management and strategy, though the transaction size is modest relative to fund operations and warrants context about Lydon's overall portfolio activity and track record. The timing during a period of downward pressure rather than at fund peaks makes this a constructive signal worth monitoring, though a single director purchase alone is insufficient to validate investment conviction without corroborating evidence from earnings, peer performance, or broader insider activity.

Director Barnes Randall C buys 220 GOF shares at $11.39; stock down 30.3% from 52-week high.

Barnes Randall C purchased 220 shares of Guggenheim Strategic Opportunities Fund at $11.39 on 2026-03-12, increasing his holdings to 6,451 shares. This transaction is modest in absolute value ($2,505.80) and represents a 3.5% increase to his existing position. The stock's current price of $11.08 is -30.3% from its 52-week high of $15.90, and GOF has declined 8.9% over the past 30 days and 9.6% over 90 days. His prior trades at GOF show mixed results: his two earlier buys (on 2025-10-30 and 2025-11-04) produced negative 90-day returns of -1.8% and -5.6% respectively, and 0 of his 2 measurable GOF buys were well-timed at the 90-day mark. While his cross-ticker track record shows a 66.67% 90-day win rate with +2.2% average 90-day return across 20 prior buys, this ticker-specific pattern does not support the same predictive confidence.

Director Barnes Randall C purchases 220 GOF shares at $11.39; holdings now 6,451 shares. Stock down 30.7% from 52-week high.

Barnes Randall C, a Director, purchased 220 shares of Guggenheim Strategic Opportunities Fund (GOF) at $11.39 on 2026-03-12, increasing holdings to 6,451 shares. The transaction represents a 3.5% increase in his position. At his prior 4 trades at GOF, measurable outcomes show 30-day and 90-day returns of -7.8% and -5.6% (2025-11-04 buy) and -4.5% and -1.8% (2025-10-30 buy), with 0 of 2 prior buys showing positive 90-day returns. The current market price of $11.02 is 30.7% below the 52-week high of $15.90, and the stock has declined 12.0% over 30 days and 9.7% over 90 days. The purchase occurs during a period of sustained weakness.

Director Randall C. Barnes bought 4,180 shares of GOF at $11.59; position now 6,231 shares (+203.8%). Stock down 29.0% from 52-week high.

Director Randall C. Barnes increased his GOF holdings by 4,180 shares (203.8%) through a $48,446.20 purchase at $11.59 per share on 2026-03-06. The stock is currently trading at $11.30, down 29.0% from its 52-week high of $15.91, and has declined 8.7% over the past 30 days. Notably, Barnes' two prior purchases at GOF in late 2025 (on 2025-11-04 and 2025-10-30) both posted negative 90-day returns of -5.6% and -1.8% respectively, indicating poor timing on those transactions. While his cross-ticker track record shows a 70.00% win rate on prior buys with an average 90-day return of +2.0%, his same-ticker history at GOF shows 0 of 2 prior buys were well-timed, suggesting the stock may not have been a favorable entry point for his recent purchases.

Director Nyberg buys 412 GOF shares at $12.13; holdings rise to 5,010 shares (+9.0%), stock now 23.0% below 52-week high

Ronald Nyberg, a director of Guggenheim Strategic Opportunities Fund, purchased 412 shares at $12.13 on 2025-12-18, increasing his position by 9.0% to 5,010 shares. The purchase occurred while the stock trades 23.0% below its 52-week high of $15.91, though recent momentum remains positive with a 30-day gain of 2.2%. Nyberg's cross-ticker track record shows 3 prior open-market buys with a 100.00% 90-day win rate and average 90-day return of +3.6%, though this cross-ticker performance does not establish a track record specifically at GOF. The timing and magnitude of this discretionary purchase merit investor attention given the fund's recent correction.

Director Randall C Barnes purchases 380 shares of GOF at $13.08; holdings increase to 1,960 shares (+24.1%)

Randall C Barnes, a Director, purchased 380 shares of GUGGENHEIM STRATEGIC OPPORTUNITIES FUND (GOF) at $13.08 on 2025-11-04, expanding his holdings from 1,580 to 1,960 shares. The stock is currently trading at $13.03, down 18.7% from its 52-week high and off 13.1% over the last 30 days. This purchase follows another GOF acquisition just four days prior (2025-10-30), suggesting sustained engagement with the fund despite recent price weakness. Across his open-market trade history, Barnes maintains a 77.78% 90-day win rate with an average 90-day return of +2.7%, though that cross-ticker track record cannot be assumed to predict outcomes at GOF, where measurable history remains limited.

Director Barnes Randall C purchases 1,580 (1.6K shares) of GOF at $13.02; stock down 17.3% from 52-week high.

Barnes Randall C, a director of Guggenheim Strategic Opportunities Fund, made his first purchase in this security, acquiring 1,580 shares at $13.02 on 2025-10-30 for a total value of $20,571.60 ($20.6K). The purchase occurs while GOF trades 17.3% below its 52-week high of $16.03 and has declined 11.6% over the past 30 days. Across his cross-ticker track record, the insider has executed 18 prior buys with an average 90-day return of +2.7% and a 90d win rate of 77.78%, though this metric reflects performance across multiple securities and provides limited insight into his prior accuracy specifically at closed-end funds or this particular holding.

Director Brock-Kyle Angela purchases 943 shares at $15.36 for $14,500.00, increasing holdings 63.4%

Brock-Kyle Angela, a Director at Guggenheim Strategic Opportunities Fund, executed 3 separate purchases totaling 943 shares for $14,500.00 on 2024-09-03 at a blended average price of $15.36. This increases her holdings from 1,488 shares to 2,431 shares, a 63.4% increase in position size. The transaction occurred at prices slightly above the current price of $15.29 and near the stock's 52-week high of $15.96 (only 4.2% below). Her prior open-market buy at this ticker on 2023-09-28 saw a -14.4% return over 90 days, suggesting timing challenges in past purchases at this fund. The cross-ticker track record shows 5 prior buys with a 50.00% win rate and average 90-day return of -1.9%, indicating mixed historical performance on timing purchases generally.