WTFC WINTRUST FINANCIAL CORP Insider Trading

WTFC C-suite insider sells ~$1.4M in stock near recent highs

A Wintrust Financial executive sold approximately 9,600 shares in a transaction totaling $1.43 million, representing a meaningful reduction of their holdings. The sale occurred when the stock was trading near its recent highs and has recently recovered well from earlier lows, suggesting the insider chose to liquidate during a strong price period. The company itself shows solid financial health with profitable operations, modest revenue growth, and a reasonable valuation multiple—fundamentals are stable rather than alarming. Without visibility into the insider's broader trading history or personal liquidity needs, this appears to be a routine portfolio rebalancing rather than a red-flag confidence signal, though the timing during strength warrants monitoring as a potential profit-taking moment.

WTFC EVP/Chief Legal Officer sells 5,000 shares at $159.61; post-sale holdings 16,883 shares (-22.8%)

Kathleen M Boege, Chief Legal Officer, sold 5,000 shares at $159.61 on 2026-02-04 for $798,050.00, reducing her stake by 22.8% to 16,883 shares. The transaction occurred near the company's 52-week high of $161.35, just 7.5% below the peak. Prior trades at WTFC on 2026-01-29 have not yet accumulated measurable 30- or 90-day outcomes to assess execution timing, and her limited cross-ticker track record (2 prior sells) provides no clear pattern of predictive timing accuracy. WTFC fundamentals remain solid with $615.7M quarterly revenue, $216.3M net income, and 13.7% annual revenue growth at a 12.72 P/E, suggesting no obvious operational concern underlying the sale.

EVP & Chief Legal Officer Kathleen Boege sells 5,000 shares at $146.38 blended average for $731.9K at WTFC

Kathleen Boege, EVP and Chief Legal Officer at Wintrust Financial, executed 2 separate sales totaling 5,000 shares for $731,908.68 on January 29, 2026, reducing her holdings by 17.9% to 22,883 shares post-transaction. The sales occurred at a blended average price of $146.38, near the current price of $147.49, with the company trading near 52-week highs and posting strong recent fundamentals including 13.7% annual revenue growth and a P/E of 12.56. The sale represents a material reduction in insider equity holdings during a period of positive price momentum (30-day +5.5%, 90-day +13.4%), though the proximity of execution price to current price limits temporal inference about execution timing.

WTFC Vice Chairman David Dykstra sold 14,942 shares at $131.53 (total $1,965,321.26) on 2025-07-29; retains 182,208 shares.

David Dykstra, Vice Chairman and COO of WTFC, sold 14,942 shares representing a -7.6% reduction of his prior holdings. The sale occurred at $131.53, modestly above the current price of $130.51 and within recent trading range context. Reviewing his track record at WTFC specifically, prior sales have shown mixed timing: two of four prior sales at this ticker achieved negative 90-day returns (-9.3% and -14.6% in Feb and Jan 2025; +19.9% and +8.7% in Oct 2024 and Feb 2024). The company shows solid fundamentals with revenue of $615,730,000.00, net income of $189,039,000.00, and annual revenue growth of +13.7%, trading at a P/E of 12.54. This sale follows a pattern of periodic liquidation activity rather than a single concentrated position exit, and occurs in a period of near-term stock strength (+5.3% over 30 days).

WTFC Vice Chairman sold 9,480 shares at $123.64; stock down 6.3% in 30 days, 9.8% in 90 days.

David A. Dykstra, Vice Chairman and COO of Wintrust Financial, sold 9,480 shares (9.5K shares) at $123.64 on 2025-02-27 for $1,172,107.20 ($1.2M), reducing his holdings from 206,455 to 196,975 shares (-4.6%). The sale occurred as WTFC stock has declined 6.3% over 30 days and 9.8% over 90 days from the transaction date, versus a 52-week range of $91.95–$138.50. Dykstra's prior trades at WTFC show mixed timing: his 2024-10-29 and 2024-02-29 sales were followed by gains (90d +12.5% and +0.2% respectively), while his most recent 2025-01-28 sale preceded a 6.5% 30-day decline. His cross-ticker sell track record (3 prior sales, avg 90d return +6.3%, 0.00% well-timed rate) reflects a pattern of selling before or coincident with upside moves, not downside—whereas this transaction has occurred during evident near-term weakness. The fundamentals remain solid (P/E 11.76, revenue +13.7% YoY, $8.3B market cap), so the sale appears discretionary rather than driven by operational concerns.

CFO David Stoehr sells 5,316 shares of WTFC for $657.1K at $123.61; stock down 6.3% in 30 days.

David Stoehr, CFO of Wintrust Financial, sold 5,316 shares (26.8% of his holdings) on 2025-02-27 at $123.61, reducing his position from 19,858 to 14,542 shares. The sale occurred as the stock declined 6.3% over the prior 30 days and 9.8% over 90 days, currently trading 10.1% below its 52-week high of $138.50. His cross-ticker track record shows 1 prior sell with an average 90-day return of 0.1% (poorly timed: the stock rose after the sale), and his single prior trade at WTFC on 2024-02-29 similarly yielded a 0.1% return over 90 days. The company fundamentals remain solid—revenue of $615.7M and net income of $170.0M in the latest quarter, with annual revenue growth of 13.7% and a P/E of 11.76—but the transaction provides no clear signal of conviction timing or concern given the insider's historical outcomes and the absence of material context.

WTFC Vice Chairman/COO David Dykstra sells 4,213 shares at $131.31; retains 206,294 post-transaction.

David A. Dykstra sold 4,213 shares (4.2K shares) of WTFC at $131.31 on 2025-01-28, reducing his holding by 2.0% to 206,294 shares. This represents his third open-market sale at WTFC; his two prior sales at this ticker (2024-10-29 and 2024-02-29) both posted positive 90-day returns of +19.9% and +8.7% respectively, indicating the stock rose after those sales—neither trade was well-timed in the directional sense. The current stock price of $132.83 is 4.1% below the 52-week high, while the broader context shows the stock has gained +6.8% over the past 30 days and +14.6% over 90 days. Dykstra's cross-ticker track record across two prior sells shows an average 90-day well-timed rate of 0.00%, meaning none of his recent open-market sales preceded declines. The transaction is modest in scale relative to his holdings and does not signal a material reduction in position conviction.

WTFC Vice Chairman Dykstra sells 15,492 shares at $115.48; retains 197,591 shares post-trade

David Dykstra, Vice Chairman and COO of Wintrust Financial, sold 15,492 shares on 2024-10-29 for $1,789,016.16, reducing his holdings by 7.3% to 197,591 shares. The sale occurred at $115.48, near the stock's 52-week high of $117.01 and ahead of recent price momentum (+8.6% over 30 days). Notably, Dykstra's only prior WTFC sale (2024-02-29) was followed by a 90-day return of +0.2%, indicating the stock rose after his last sale; his cross-ticker track record shows 0.00% well-timed rate for all sells, meaning prior sales were not preceded market declines. The fundamentals remain solid with a P/E of 12.27, annual revenue growth of +1.2%, and $152.4M quarterly net income, suggesting no distress signal. The transaction itself is open-market and relatively modest in scope given his remaining 197.6K share position.