Joseph Stilwell Biography and Net Worth

Director of Kingsway Financial Services

Joseph D. Stilwell is the owner and managing member of Stilwell Value LLC, the General Partner of a group of funds known as The Stilwell Group. He graduated in 1983 from the Wharton School at the University of Pennsylvania with a Bachelor of Science in Economics.

What is Joseph Stilwell's net worth?: The estimated net worth of Joseph Stilwell is at least $3.83 million as of March 26th, 2025. Mr. Stilwell owns 498,937 shares of Kingsway Financial Services stock worth more than $3,832,834 as of April 3rd. This net worth approximation does not reflect any other assets that Mr. Stilwell may own. Learn More about Joseph Stilwell's net worth.
How do I contact Joseph Stilwell?: The corporate mailing address for Mr. Stilwell and other Kingsway Financial Services executives is 150 E. Pierce Road, Itasca IL, 60143. Kingsway Financial Services can also be reached via phone at (312) 766-2144 and via email at aprior@equityny.com. Learn More on Joseph Stilwell's contact information.
Has Joseph Stilwell been buying or selling shares of Kingsway Financial Services?: Joseph Stilwell has not been actively trading shares of Kingsway Financial Services within the last three months. Most recently, Joseph Stilwell sold 1,000,000 shares of the business's stock in a transaction on Wednesday, March 26th. The shares were sold at an average price of $8.00, for a transaction totalling $8,000,000.00. Following the completion of the sale, the director now directly owns 498,937 shares of the company's stock, valued at $3,991,496. Learn More on Joseph Stilwell's trading history.
Who are Kingsway Financial Services' active insiders?: Kingsway Financial Services' insider roster includes John Fitzgerald (CEO), Kent Hansen (CFO), and Joseph Stilwell (Director). Learn More on Kingsway Financial Services' active insiders.
Are insiders buying or selling shares of Kingsway Financial Services?: During the last twelve months, Kingsway Financial Services insiders bought shares 23 times. They purchased a total of 5,927 shares worth more than $50,010.37. During the last twelve months, insiders at the insurance provider sold shares 4 times. They sold a total of 1,490,000 shares worth more than $12,109,450.00. The most recent insider tranaction occured on March, 28th when CEO John Taylor Maloney Fitzgerald bought 305 shares worth more than $2,501.00. Insiders at Kingsway Financial Services own 54.8% of the company. Learn More about insider trades at Kingsway Financial Services.
Information on this page was last updated on 3/28/2025.

Joseph Stilwell Insider Trading History at Kingsway Financial Services

Transaction Date	Buy/Sell	Number of Shares	Average Share Price	Total Transaction	Shares Held After Transaction
3/26/2025	Sell	1,000,000	$8.00	$8,000,000.00	498,937
12/18/2024	Sell	365,000	$8.43	$3,076,950.00	593,743
11/19/2024	Sell	25,000	$8.78	$219,500.00	636,159
6/28/2024	Sell	100,000	$8.13	$813,000.00	640,108
3/11/2024	Sell	7,300	$8.76	$63,948.00	648,797
3/8/2024	Sell	13,095	$8.84	$115,759.80	649,432
3/13/2023	Sell	65,000	$9.03	$586,950.00	659,454
6/21/2022	Buy	15,000	$5.32	$79,800.00	5,047,525
6/16/2022	Buy	8,724	$5.30	$46,237.20	5,037,473
6/14/2022	Buy	10,000	$5.30	$53,000.00	5,027,523
6/6/2022	Buy	10,000	$5.40	$54,000.00	4,992,648
3/30/2022	Buy	10,000	$5.50	$55,000.00
3/28/2022	Buy	10,000	$5.50	$55,000.00
3/25/2022	Buy	10,000	$5.50	$55,000.00
3/23/2022	Buy	10,000	$5.50	$55,000.00
3/21/2022	Buy	2,795	$5.50	$15,372.50
3/18/2022	Buy	10,000	$5.50	$55,000.00
3/16/2022	Buy	10,000	$5.50	$55,000.00
3/14/2022	Buy	500	$5.54	$2,770.00
3/10/2022	Buy	1,212	$5.50	$6,666.00
3/8/2022	Buy	10,000	$5.39	$53,900.00
12/29/2021	Buy	10,000	$5.49	$54,900.00
12/27/2021	Buy	9,083	$5.50	$49,956.50
12/22/2021	Buy	10,000	$5.50	$55,000.00
12/20/2021	Buy	10,000	$5.47	$54,700.00
12/17/2021	Buy	10,000	$5.50	$55,000.00
12/15/2021	Buy	300	$5.44	$1,632.00
12/13/2021	Buy	10,000	$5.50	$55,000.00
12/8/2021	Buy	10	$5.18	$51.80
12/6/2021	Buy	2,698	$5.04	$13,597.92
12/2/2021	Buy	10,000	$5.34	$53,400.00
11/30/2021	Buy	5,178	$5.40	$27,961.20
11/26/2021	Buy	10,000	$5.47	$54,700.00
11/24/2021	Buy	10,000	$5.45	$54,500.00
11/22/2021	Buy	10,000	$5.50	$55,000.00
11/18/2021	Buy	10,000	$5.50	$55,000.00
11/15/2021	Buy	8,733	$5.40	$47,158.20
11/12/2021	Buy	9,115	$5.40	$49,221.00
9/22/2021	Buy	19,127	$5.25	$100,416.75
9/16/2021	Buy	10,000	$5.35	$53,500.00
9/8/2021	Buy	10,000	$5.35	$53,500.00
8/26/2021	Buy	5,000	$5.35	$26,750.00
8/20/2021	Buy	11,425	$5.27	$60,209.75
8/18/2021	Buy	8,517	$5.36	$45,651.12
12/28/2020	Buy	10,000	$4.62	$46,200.00
12/23/2020	Buy	5,400	$4.61	$24,894.00
12/21/2020	Buy	5,000	$4.58	$22,900.00
12/18/2020	Buy	5,000	$4.50	$22,500.00
12/16/2020	Buy	5,000	$4.35	$21,750.00
12/14/2020	Buy	9,701	$4.30	$41,714.30
12/11/2020	Buy	10,000	$4.30	$43,000.00
9/18/2020	Buy	190,000	$3.10	$589,000.00
9/16/2020	Buy	35,000	$3.03	$106,050.00
9/14/2020	Buy	36,307	$2.96	$107,468.72
9/10/2020	Buy	25,412	$2.96	$75,219.52
9/8/2020	Buy	25,000	$2.95	$73,750.00
9/3/2020	Buy	25,000	$2.90	$72,500.00
8/27/2020	Buy	86,574	$2.79	$241,541.46
8/24/2020	Buy	13,000	$2.72	$35,360.00
3/29/2019	Buy	135,341	$3.01	$407,376.41
3/27/2019	Buy	24,400	$2.78	$67,832.00
3/25/2019	Buy	189,144	$2.41	$455,837.04
3/21/2019	Buy	74,213	$2.30	$170,689.90
12/31/2018	Buy	445,919	$2.70	$1,203,981.30
12/31/2018	Buy	563,614	$2.57	$1,448,487.98
12/28/2018	Buy	117,695	$2.09	$245,982.55
11/15/2018	Buy	20,000	$2.72	$54,400.00
9/24/2018	Buy	27,900	$2.95	$82,305.00
9/20/2018	Buy	9,100	$2.96	$26,936.00
9/14/2018	Buy	75,000	$2.85	$213,750.00
9/12/2018	Buy	343,101	$2.72	$933,234.72
12/28/2017	Buy	2,566	$5.05	$12,958.30
12/28/2017	Buy	2,566	$5.05	$12,958.30
12/26/2017	Buy	2,500	$5.05	$12,625.00
12/21/2017	Buy	5,000	$5.18	$25,900.00
12/19/2017	Buy	2,500	$5.39	$13,475.00
12/14/2017	Buy	10,000	$5.02	$50,200.00
12/12/2017	Sell	60,000	$5.04	$302,400.00
9/29/2017	Buy	10,100	$6.10	$61,610.00
9/28/2017	Buy	2,500	$6.10	$15,250.00
9/27/2017	Buy	2,500	$6.01	$15,025.00
9/26/2017	Buy	2,500	$6.05	$15,125.00
9/25/2017	Buy	2,500	$5.96	$14,900.00
9/22/2017	Buy	2,500	$5.86	$14,650.00
9/21/2017	Buy	5,000	$5.81	$29,050.00
9/20/2017	Buy	5,000	$5.90	$29,500.00
9/19/2017	Buy	1,794	$5.95	$10,674.30
9/18/2017	Buy	2,500	$5.95	$14,875.00
9/15/2017	Buy	2,586	$5.95	$15,386.70
9/14/2017	Buy	3,520	$5.95	$20,944.00
9/13/2017	Buy	2,500	$5.95	$14,875.00
9/12/2017	Buy	2,500	$5.90	$14,750.00
9/8/2017	Buy	2,500	$5.65	$14,125.00
9/6/2017	Buy	7,500	$5.78	$43,350.00
9/1/2017	Buy	2,500	$6.00	$15,000.00
8/31/2017	Buy	1,000	$5.95	$5,950.00
8/30/2017	Buy	2,500	$5.90	$14,750.00
8/29/2017	Buy	1,400	$5.80	$8,120.00
8/21/2017	Buy	2,500	$5.95	$14,875.00
8/18/2017	Buy	400	$5.95	$2,380.00
8/17/2017	Buy	800	$5.85	$4,680.00
8/16/2017	Buy	2,500	$5.90	$14,750.00
8/15/2017	Buy	1,700	$5.90	$10,030.00
6/30/2017	Buy	5,000	$6.10	$30,500.00
6/29/2017	Buy	800	$6.05	$4,840.00
6/28/2017	Buy	4,200	$6.06	$25,452.00
6/27/2017	Buy	200	$6.05	$1,210.00
6/26/2017	Buy	10,000	$6.08	$60,800.00
5/9/2017	Buy	2,000	$6.00	$12,000.00
5/5/2017	Buy	2,000	$5.90	$11,800.00
5/4/2017	Buy	2,000	$5.85	$11,700.00
5/3/2017	Buy	2,000	$5.95	$11,900.00
5/2/2017	Buy	1,000	$5.90	$5,900.00
5/1/2017	Buy	1,077	$5.65	$6,085.05
4/28/2017	Buy	2,000	$5.50	$11,000.00
3/31/2017	Buy	10,400	$5.84	$60,736.00
3/30/2017	Buy	10,000	$5.88	$58,800.00
3/28/2017	Buy	5,038	$5.80	$29,220.40
3/27/2017	Buy	6,200	$5.80	$35,960.00
3/22/2017	Buy	10,000	$5.82	$58,200.00
3/21/2017	Buy	5,000	$5.90	$29,500.00
3/17/2017	Buy	4,700	$5.70	$26,790.00
3/16/2017	Buy	16,100	$5.71	$91,931.00
9/30/2016	Buy	1,148,263	$5.74	$6,591,029.62
6/1/2016	Buy	96,737	$4.97	$480,782.89	3,772,218
1/14/2016	Buy	6,892	$3.99	$27,499.08	3,772,218
8/20/2013	Buy	10,000	$3.03	$30,300.00
8/15/2013	Buy	5,400	$3.12	$16,848.00
8/14/2013	Buy	24,600	$3.11	$76,506.00
6/14/2013	Buy	1,356	$3.40	$4,610.40
6/11/2013	Buy	335,000	$3.64	$1,219,400.00
11/29/2012	Buy	1,265	$2.41	$3,048.65
11/27/2012	Buy	25,000	$2.30	$57,500.00
11/23/2012	Buy	1,600	$2.30	$3,680.00
10/15/2012	Buy	13,116	$4.12	$54,037.92
10/11/2012	Buy	4,890	$3.95	$19,315.50
10/10/2012	Buy	10,000	$3.61	$36,100.00
10/8/2012	Buy	10,500	$3.05	$32,025.00
10/3/2012	Buy	9,372	$2.82	$26,429.04
10/2/2012	Buy	10,600	$2.24	$23,744.00
9/28/2012	Buy	14,000	$2.14	$29,960.00
9/27/2012	Buy	5,200	$2.09	$10,868.00
9/26/2012	Buy	20,336	$2.05	$41,688.80
9/25/2012	Buy	4,100	$2.01	$8,241.00
9/21/2012	Buy	1,190	$2.05	$2,439.50
9/20/2012	Buy	16,900	$2.10	$35,490.00
9/19/2012	Buy	78,200	$2.03	$158,746.00
8/15/2012	Buy	3,700	$2.07	$7,659.00

See Full Table

Joseph Stilwell Buying and Selling Activity at Kingsway Financial Services

Kingsway Financial Services Company Overview

Kingsway Financial Services Inc., through its subsidiaries, engages in the extended warranty and business services in the United States. The company operates through two segments, Extended Warranty and Kingsway Search Xcelerator. The Extended Warranty segment markets, sells, and administers vehicle service agreements and related products for new and used automobiles, motorcycles, and ATVs. This segment also markets and distributes warranty products to manufacturers, distributors, and installers of heating, ventilation and air conditioning, standby generator, commercial LED lighting, and commercial refrigeration equipment; and provides equipment breakdown and maintenance support services to companies, as well as after-market vehicle protection services. The Kingsway Search Xcelerator offers outsourced finance and human resources consulting services, including operational accounting, such as bookkeeping, accounting, financial reporting, and analysis and strategic finance services; technical accounting comprising initial public offerings, Securities and Exchange Commission reporting, and international consolidation services; human resources, workforce management, and compliance support services; and advisory services. This segment also provides financial executive services for project and interim staffing engagements; search services for permanent placements; healthcare staffing services to acute healthcare facilities for short-term and day-to-day needs of hospitals; software products for the management needs of all types of shared-ownership properties; and fully managed outsourced cardiac telemetry services, as well as provides mobile monitors to the hospitals. The company offers its products and services through credit unions and dealers. Kingsway Financial Services Inc. was incorporated in 1989 and is headquartered in Chicago, Illinois.

Today's Range

Now: $7.76

$7.64

$7.82

50 Day Range

MA: $7.83

$7.27

$8.27

2 Week Range

Now: $7.76

$7.06

$9.58

Volume

34,292 shs

Average Volume

53,457 shs

Market Capitalization

$213.55 million

P/E Ratio

N/A

Dividend Yield

N/A

Beta

N/A

Joseph Stilwell Biography and Net Worth

What is Joseph Stilwell's net worth?

How do I contact Joseph Stilwell?

Has Joseph Stilwell been buying or selling shares of Kingsway Financial Services?

Who are Kingsway Financial Services' active insiders?

Are insiders buying or selling shares of Kingsway Financial Services?

Joseph Stilwell Insider Trading History at Kingsway Financial Services

Joseph Stilwell Buying and Selling Activity at Kingsway Financial Services

Kingsway Financial Services Company Overview

Today's Range

50 Day Range

2 Week Range

Volume

Average Volume

Market Capitalization

P/E Ratio

Dividend Yield

Beta