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Insider Cluster (3 insiders) ·Filed Aug 18, 2026

KWY

KINGSWAY Corp
BEARISH
Impact 5/10
Horizondays Processed2mo ago
Insider cluster: 2 insiders, $410K total
Actionable Insight ▼ Bearish

The dominant signal is a $1.0M open-market sale by a director/10% owner—0.35% of market cap, which is modest but notable. The token purchases by CEO/CFO on Aug 17 are too small to offset. Monitor for an 8-K regarding operations or guidance; if negative news emerges, this insider selling was prescient.

DirectionBearish
Confidencemedium
Horizondays
Latest settled — T+20d
KWY ▼ -2.22% at T+20d
SHORT call ✓ call won +2.22% · α vs SPY +1.38% · entry $9.89 → $9.67
Next anchor: T+60d in 15d
Latest observation: T+46 -14.86% FF3 residual α
Entry = T+0 close
Aug 18, 2026
via day close
T+1d
+1.42%
call -1.42% · α -2.26%
$10.03
settled 2mo ago
T+5d
+2.73%
call -2.73% · α -3.12%
$10.16
settled 2mo ago
T+20d
-2.22%
call +2.22% · α +1.38%
$9.67
settled 6w ago
T+60d
Pending
in 15d

Price Chart

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Executive Summary

A mixed insider cluster at Kingsway Corp: President/CEO Maloney and CFO Hansen bought small open-market amounts (~$4K combined), while Director Stilwell sold a substantial $1.0M worth of shares at $10.00. The selling by a 10% owner on August 13 far outweighs the tiny insider purchases in dollar terms (0.35% of market cap vs. 0.001%).

Key Financial Metrics

Direction
mixed
Total Value
$1.0M
Insiders
3

Key Facts

  • Director Stilwell Joseph sold 100,000 shares total on August 13, 2026, netting $1,000,000 at $10.00 per share.
  • CEO Fitzgerald John Taylor Maloney bought 254 shares ($2,507) on August 17 at $9.87.
  • CFO Hansen Kent A bought 158 shares ($1,559) on August 17 at $9.87.
  • Total insider selling ($1,000,000) equals 0.35% of KWY's $284M market cap.
  • Total insider buying ($4,066) is negligible at 0.001% of market cap.

Financial Impact

Director sold $1.0M in a single day; CFO and CEO made combined $4K purchases 4 days later.

insider ownershipfloat

Risk Factors

  • Director's large sell may signal adverse business conditions or upcoming bad news.
  • Token insider buys by C-suite may be window-dressing or routine dollar-cost averaging.

Market Snapshot

Exchange
NYSE
Sector
Fire, Marine & Casualty Insurance

Documents Analyzed

This report is based on 1 SEC document filed with EDGAR.

DocumentAccession Number
CLUSTER Data (Synthetic)cluster-KWY-1787119823258
8 reports for KWY
Performance horizon

Track record builds as more directional reports settle.

Filters
Rows
Reports for KWY — sortable, filterable
TypeNow
Aug 20, 2026
9w ago
Insider Cluster
BEARISH ★ 4/10
$10.42 $9.79▲ +6.05%▲ +5.52%$9.97 (+4.32%)
Aug 18, 2026
9w ago
Insider Cluster
BEARISH ★ 5/10
$9.89 $9.67▲ +2.22%▲ +1.38%$9.97 (−0.81%)
Jul 1, 2026
16w ago
Insider Cluster
NEUTRAL ★ 2/10
$10.50 $8.91▼ −15.14%▼ −15.45%$9.97 (−5.05%)
Jun 15, 2026
19w ago
Insider Cluster
NEUTRAL ★ 2/10
$10.48 $9.76▼ −6.87%▼ −7.07%$9.97 (−4.87%)
Jun 15, 2026
19w ago
Insider Cluster
NEUTRAL ★ 2/10
$10.48 $9.76▼ −6.87%▼ −7.07%$9.97 (−4.87%)
Jun 1, 2026
21w ago
Insider Cluster
NEUTRAL ★ 2/10
$10.17 $10.44▲ +2.65%▲ +4.22%$9.97 (−1.97%)
Jun 1, 2026
21w ago
Insider Cluster
NEUTRAL ★ 2/10
$10.17 $10.44▲ +2.65%▲ +4.22%$9.97 (−1.97%)
May 22, 2026
22w ago
Insider Cluster
NEUTRAL ★ 3/10
$10.02 $10.76▲ +7.34%▲ +9.28%$9.97 (−0.50%)
Showing 8 of 8

US Market Status

Market Open — Closes in 4m

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Report published Aug 19, 2026