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Insider Cluster (4 insiders) ·Filed Aug 20, 2026

KWY

KINGSWAY Corp
BEARISH
Impact 4/10
Horizondays Processed2mo ago
Insider cluster: 4 insiders, $0.4M total
Actionable Insight ▼ Bearish

The cluster is dominated by a director/10% owner selling $409K — a 23:1 sell-to-buy ratio by value. C-suite buys are token amounts (<$3K each) and do not offset the signal. Monitor for any upcoming 8-K filings (earnings, guidance, or material developments) that may have prompted the sale.

DirectionBearish
Confidencemedium
Horizondays
Latest settled — T+20d
KWY ▼ -6.05% at T+20d
SHORT call ✓ call won +6.05% · α vs SPY +5.52% · entry $10.42 → $9.79
Next anchor: T+60d in 17d
Latest observation: T+44 -3.32% FF3 residual α
Entry = T+0 close
Aug 20, 2026
via day close
T+1d
+2.21%
call -2.21% · α -2.50%
$10.65
settled 2mo ago
T+5d
-1.73%
call +1.73% · α +2.20%
$10.24
settled 2mo ago
T+20d
-6.05%
call +6.05% · α +5.52%
$9.79
settled 6w ago
T+60d
Pending
in 17d

Price Chart

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Executive Summary

KWY insider cluster shows mixed signals: Director/10% owner Stilwell Joseph sold $409K worth of shares at $10.00, while CEO Fitzgerald, CFO Hansen, and Director Horowitz made small open-market purchases totaling ~$18K. The selling by a major holder ($409K = 0.14% of market cap) is modest but notable given the buys are trivial in size. The cluster is dominated by a single large sale from a director/10% owner, with C-suite buys too small to offset the signal.

Key Financial Metrics

Direction
selling
Total Value
$391.0K
Insiders
4

Key Facts

  • Director/10% owner Stilwell Joseph sold 40,900 shares at $10.00 for $409,000 on 2026-08-13
  • CEO Fitzgerald purchased 254 shares at $9.87 for ~$2,507 on 2026-08-17
  • CFO Hansen purchased 158 shares at $9.87 for ~$1,559 on 2026-08-17
  • Director Horowitz purchased 1,300 shares at $9.75 for $12,675 on 2026-08-18
  • Total insider selling of $409K vs. total insider buying of ~$18K — a 23:1 ratio by dollar value
  • Stilwell's sale represents 0.14% of KWY's $286M market cap — modest but the only material trade in the cluster

Financial Impact

$409K in insider selling vs. $18K in insider buying; net selling of ~$391K

insider ownershipmarket sentiment

Risk Factors

  • Stilwell's sale could signal negative non-public information about KWY's insurance operations or reserves
  • Token C-suite buys may be window-dressing or 10b5-1 plan purchases, not conviction signals
  • Insurance sector headwinds (catastrophe losses, reserve adequacy) could be the unstated reason for the sale

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-1787266881623
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%$9.85 (+5.47%)
Aug 18, 2026
9w ago
Insider Cluster
BEARISH ★ 5/10
$9.89 $9.67▲ +2.22%▲ +1.38%$9.85 (+0.40%)
Jul 1, 2026
16w ago
Insider Cluster
NEUTRAL ★ 2/10
$10.50 $8.91▼ −15.14%▼ −15.45%$9.85 (−6.19%)
Jun 15, 2026
19w ago
Insider Cluster
NEUTRAL ★ 2/10
$10.48 $9.76▼ −6.87%▼ −7.07%$9.85 (−6.01%)
Jun 15, 2026
19w ago
Insider Cluster
NEUTRAL ★ 2/10
$10.48 $9.76▼ −6.87%▼ −7.07%$9.85 (−6.01%)
Jun 1, 2026
21w ago
Insider Cluster
NEUTRAL ★ 2/10
$10.17 $10.44▲ +2.65%▲ +4.22%$9.85 (−3.15%)
Jun 1, 2026
21w ago
Insider Cluster
NEUTRAL ★ 2/10
$10.17 $10.44▲ +2.65%▲ +4.22%$9.85 (−3.15%)
May 22, 2026
22w ago
Insider Cluster
NEUTRAL ★ 3/10
$10.02 $10.76▲ +7.34%▲ +9.28%$9.85 (−1.70%)
Showing 8 of 8

US Market Status

Market Closed — Opens Wed (11h 57m)

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Report published Aug 20, 2026