Charles Brent Jr. Winn

CFO Charles Brent Jr. Winn buys 1,640 shares of MDRR at $10.42; stock down 29.6% from 52-week high, prior MDRR buys all negative at 90 days.

Charles Brent Jr. Winn, Chief Financial Officer, purchased 1,640 shares at $10.42, bringing his holdings to 62,585 shares from 60,945 shares. This transaction occurs while the stock trades at $10.23, down 29.6% from its 52-week high of $14.52 and down 8.7% over 30 days and 13.0% over 90 days. His prior trading history at MDRR reveals a consistent pattern: all 5 of his preceding buys at this ticker recorded negative 90-day returns, ranging from -0.9% to -14.4%, indicating none were well-timed at the 90-day mark. The current purchase aligns with this pattern of activity in a declining security, warranting close monitoring of whether this transaction proves a departure from his recent execution outcomes at this specific holding.

CFO Winn Charles Brent Jr. buys 1,188 shares at $11.46 avg as MDRR stock down 21.0% from 52-week high.

CFO Winn Charles Brent Jr. executed 3 separate purchases totaling 1,188 shares for $13,613.20 on 2026-03-05 and 2026-03-06, expanding his holdings by 2.0% to 60,390 shares. The transaction occurred at $11.46 blended average price, near current levels of $11.42 but representing accumulation during a period of weakness: the stock is -21.0% from its 52-week high of $14.45 and down 12.8% over the trailing 90 days. However, his prior 5 trades at MDRR show a concerning pattern—0 of 4 measurable prior buys were well-timed at the 90-day mark, with outcomes ranging from -0.5% to -14.4% returns, suggesting systematic misalignment between purchase timing and subsequent price direction at this ticker. Against that backdrop, Medalist Diversified posted negative net income of $-395,948.00 in the latest quarter despite 6.8% annual revenue growth, indicating ongoing profitability challenges that warrant scrutiny of the decision to accumulate shares at current levels.

CFO Winn Charles Brent Jr. buys 400 shares of MDRR at $12.66; third consecutive buy in 7 days amid -5.2% annual revenue decline and -$395.9K net loss.

Winn Charles Brent Jr., Chief Financial Officer of Medalist Diversified REIT, Inc., purchased 400 shares at $12.66 on 2025-12-10, bringing his holdings to 55,202 shares. This is the third buy transaction in seven days (following purchases on 2025-12-04, 2025-12-03, and 2025-12-02), suggesting sustained accumulation despite challenging fundamentals: the company reported Revenue $2,786,241.00 with Net income $-395,948.00 in the latest quarter, and Annual revenue growth (FY vs prior FY) of -5.2%. Across his prior trades at MDRR, the insider's timing has been mixed—1 of 2 measurable prior buys achieved positive 90-day returns (the 2025-08-13 purchase returned +15.4% over 90 days), while the 2025-09-05 buy returned -0.5% over 90 days. The stock currently trades at $13.03, up 4.2% over the past 30 days but down 6.1% over 90 days, positioning the recent purchase price near the mid-range of the 52-week span ($10.09–$14.48).

CFO Winn Charles Brent Jr. buys 252 shares at blended average $13.42 over 2 trades

Winn Charles Brent Jr., CFO of Medalist Diversified REIT, executed 2 separate open-market purchases totaling 252 shares for $3,382.54 on 2025-12-03 and 2025-12-04, bringing his holdings to 54,802 shares. The blended average purchase price of $13.42 sits above the current price of $13.10, representing a modest near-term unrealized loss. Reviewing his same-ticker history at MDRR, 3 of 4 prior measurable trades showed positive 90-day returns, though the most recent purchase on 2025-09-05 posted -0.5% at the 90-day mark. The company faces fundamental headwinds: latest quarterly revenue of $2,786,241.00 with a net loss of $-395,948.00, annual revenue decline of -5.2%, and a highly elevated P/E of 545.83 driven by minimal profitability. The transaction is modest in size relative to the CFO's existing position and does not constitute a significant portfolio shift.

CFO Winn Charles Brent Jr. buys 59 shares of MDRR at $13.35; holdings now 54,550 shares. Stock -7.2% from 52-week high on negative revenue trend.

CFO Winn Charles Brent Jr. purchased 59 shares of Medalist Diversified REIT at $13.35 on 2025-12-02, increasing holdings from 54,491 to 54,550 shares. While his cross-ticker track record shows an 83.33% win rate on prior buys with avg 90d return +9.4%, his prior trades at MDRR present mixed results: 3 of 3 measurable 90-day outcomes were positive (90d returns of +15.4%, +18.2%, +1.1%), but the company faces headwinds — revenue declined -5.2% year-over-year and latest quarter net income was -$395.9K. The stock trades at -7.2% from its 52-week high of $14.48, and this buy follows a -8.5% 30-day loss on his prior MDRR purchase (2025-05-28). The small share increment (+0.1% vs existing holdings) suggests a modest position adjustment rather than aggressive conviction in a fundamentally deteriorating business.

CFO buys 117 MDRR shares at $13.50; holds 54,491 shares post-transaction. 3 of 3 prior buys at ticker well-timed on 90d basis.

Winn Charles Brent Jr., Chief Financial Officer of Medalist Diversified REIT, Inc., purchased 117 shares at $13.50 on 2025-09-05, expanding his holdings to 54,491 shares. This represents a modest acquisition in absolute terms ($1,579.50), but the timing context is notable: his prior trades at MDRR show a clean pattern—3 of 3 prior buys were well-timed at the 90-day mark, with recent August purchases showing 30d returns of +28.0% and +28.1%. The stock has risen 31.4% over the past 90 days and currently trades at $13.99, -3.4% from its 52-week high of $14.48. However, the company's fundamentals present headwinds: negative net income of $-456,444.00 in the latest quarter, annual revenue declining 5.2% year-over-year, and an extremely elevated P/E ratio of 582.92, reflecting distorted earnings metrics. The buy occurs after strong near-term price momentum but in the context of operational strain and deteriorating revenue trends.

CFO Winn Charles Brent Jr. bought 1,115 shares at avg $10.79 (Aug 12-13); prior MDRR trades underwater, cross-ticker record strong but irrelevant here.

Winn Charles Brent Jr., CFO of MDRR, executed 2 separate purchases totaling 1,115 shares for $12,025.44 at blended average price of $10.79, representing a 2.1% increase to his holdings of 54.4K shares. The current price of $10.85 is only marginally above the transaction average, and the stock is down 25.1% from its 52-week high. However, his prior open-market trading record at this same ticker shows consistent negative returns: all 5 prior MDRR buys recorded 30-day losses ranging from -1.7% to -8.5%, with 90-day outcomes not yet measurable. While his cross-ticker track record shows an 85.71% 90-day win rate with average 90-day returns of 38.9%, that track record is not predictive of his MDRR-specific outcomes, which have been consistently underwater. The company's fundamentals are weak: quarterly revenue is $2.5M with a net loss of $-456.4K, and the valuation is stretched at a P/E of 452.08.

CFO Winn Charles Brent Jr. bought 54 shares of MDRR at $11.75; stock down 9.0% in 90 days despite his strong cross-ticker track record.

CFO Winn Charles Brent Jr. purchased 54 shares of Medalist Diversified REIT, Inc. (MDRR) at $11.75 on 2025-05-28, adding to a position that now stands at 53,259 shares. While his cross-ticker track record shows 20 prior buys with an average 90-day return of +47.1% and a win rate of 92.86%, this ticker-specific context is notably different: MDRR itself has declined 9.0% over the past 90 days and currently trades 18.8% below its 52-week high of $14.48. The company faces headwinds, with net income of $-1.0M against quarterly revenue of $2.3M and annual revenue contraction of 5.2%. The CFO's repeated purchases—this is his fifth buy at MDRR in just six trading days (2025-05-16 through 2025-05-28)—occur against deteriorating fundamentals and a stock in decline, and none of his prior same-ticker purchases have yet reached measurable outcomes. This pattern warrants attention to whether the accumulation reflects contrarian conviction or other motivations.

CFO Winn Charles Brent Jr. buys 63 shares of MDRR at $11.75 (2 transactions totaling $740.25)

Winn Charles Brent Jr., Chief Financial Officer of Medalist Diversified REIT, Inc., executed 2 separate purchases totaling 63 shares for $740.25 on 2025-05-27, increasing his holdings from 53.1K to 53.2K shares (+0.1% net change). The transaction occurred at $11.75 per share, which is 18.8% below the 52-week high of $14.48 and represents a 1.2% decline over the preceding 30 days. The company faces material headwinds: net income was negative $-1.0M in the latest quarter despite revenue of $2.3M, annual revenue contracted 5.2%, and the stock trades at a P/E of 489.58 with a market cap of $15.9M. While the CFO's cross-ticker track record shows strong timing metrics (20 prior buys averaging +50.8% return at 30 days and +51.2% at 90 days, with a 93.33% win rate), his 5 prior purchases at MDRR have not yet reached measurable outcome windows. The modest share addition relative to existing holdings, combined with deteriorating fundamentals, offers limited insight into management's forward assessment of company prospects.

CFO Winn Charles Brent Jr. purchased 97 shares at $11.75 across 2 transactions at MDRR amid negative fundamentals.

Winn Charles Brent Jr., CFO of Medalist Diversified REIT, made 2 separate purchases totaling 97 shares for $1,139.75 on 2025-05-23 at a blended average price of $11.75. His holdings grew modestly from 53,045 to 53,142 shares (+0.2%). The company is displaying material financial stress: latest quarterly revenue of $2.3M contracted 5.2% year-over-year, and net income stands at $-1.0M (negative), yielding an extreme P/E of 498.75 on a $16.2M market cap. The current share price of $11.97 sits 17.3% below the 52-week high, though the stock has recovered 6.7% over the past 30 days. His prior MDRR purchases from December 2024 and May 2025 remain early in their outcome windows; same-ticker timing data is not yet measurable for recent trades. Cross-ticker, his broader track record shows strong historical returns (average 90-day return +53.4%, 93.75% win rate), but this isolated REIT trade against deteriorating company financials suggests a small, incremental position addition with limited conviction signals.