SECURITIES AND EXCHANGE COMMISSION

Washington, D.C. 20549

x

Rule 13d-1(b)

o

Rule 13d-1(c)

o

Rule 13d-1(d)

CUSIP No. 690370101

13G

1

Names of Reporting Person/I.R.S. Identification Nos. of Above Persons (Entities Only)
V. PREM WATSA

2

Check the Appropriate Box if a Member of a Group

(a)

o

(b)

x

3

SEC Use Only

4

Citizenship or Place of Organization
CANADIAN

Number of
Shares
Beneficially
Owned by
Each
Reporting
Person With

5

Sole Voting Power

6

Shared Voting Power
3,184,677

7

Sole Dispositive Power

8

Shared Dispositive Power
3,184,677

9

Aggregate Amount Beneficially Owned by Each Reporting Person
3,184,677

10

Check Box if the Aggregate Amount in Row (9) Excludes Certain Shares  o

11

Percent of Class Represented by Amount in Row 9
12.6%

12

Type of Reporting Person
IN

CUSIP No. 690370101

13G

1

Names of Reporting Person/I.R.S. Identification Nos. of Above Persons (Entities Only)
1109519 ONTARIO LIMITED

2

Check the Appropriate Box if a Member of a Group

(a)

o

(b)

x

3

SEC Use Only

4

Citizenship or Place of Organization
ONTARIO, CANADA

Number of
Shares
Beneficially
Owned by
Each
Reporting
Person With

5

Sole Voting Power

6

Shared Voting Power
3,184,677

7

Sole Dispositive Power

8

Shared Dispositive Power
3,184,677

9

Aggregate Amount Beneficially Owned by Each Reporting Person
3,184,677

10

Check Box if the Aggregate Amount in Row (9) Excludes Certain Shares  o

11

Percent of Class Represented by Amount in Row 9
12.6%

12

Type of Reporting Person
CO

CUSIP No. 690370101

13G

1

Names of Reporting Person/I.R.S. Identification Nos. of Above Persons (Entities Only)
THE SIXTY TWO INVESTMENT COMPANY LIMITED

2

Check the Appropriate Box if a Member of a Group

(a)

o

(b)

x

3

SEC Use Only

4

Citizenship or Place of Organization
BRITISH COLUMBIA, CANADA

Number of
Shares
Beneficially
Owned by
Each
Reporting
Person With

5

Sole Voting Power

6

Shared Voting Power
3,184,677

7

Sole Dispositive Power

8

Shared Dispositive Power
3,184,677

9

Aggregate Amount Beneficially Owned by Each Reporting Person
3,184,677

10

Check Box if the Aggregate Amount in Row (9) Excludes Certain Shares  o

11

Percent of Class Represented by Amount in Row 9
12.6%

12

Type of Reporting Person
CO

CUSIP No. 690370101

13G

1

Names of Reporting Person/I.R.S. Identification Nos. of Above Persons (Entities Only)
810679 ONTARIO LIMITED

2

Check the Appropriate Box if a Member of a Group

(a)

o

(b)

x

3

SEC Use Only

4

Citizenship or Place of Organization
ONTARIO, CANADA

Number of
Shares
Beneficially
Owned by
Each
Reporting
Person With

5

Sole Voting Power

6

Shared Voting Power
3,184,677

7

Sole Dispositive Power

8

Shared Dispositive Power
3,184,677

9

Aggregate Amount Beneficially Owned by Each Reporting Person
3,184,677

10

Check Box if the Aggregate Amount in Row (9) Excludes Certain Shares  o

11

Percent of Class Represented by Amount in Row 9
12.6%

12

Type of Reporting Person
CO

CUSIP No. 690370101

13G

1

Names of Reporting Person/I.R.S. Identification Nos. of Above Persons (Entities Only)
FAIRFAX FINANCIAL HOLDINGS LIMITED

2

Check the Appropriate Box if a Member of a Group

(a)

o

(b)

x

3

SEC Use Only

4

Citizenship or Place of Organization
CANADA

Number of
Shares
Beneficially
Owned by
Each
Reporting
Person With

5

Sole Voting Power

6

Shared Voting Power
3,184,677

7

Sole Dispositive Power

8

Shared Dispositive Power
3,184,677

9

Aggregate Amount Beneficially Owned by Each Reporting Person
3,184,677

10

Check Box if the Aggregate Amount in Row (9) Excludes Certain Shares  o

11

Percent of Class Represented by Amount in Row 9
12.6%

12

Type of Reporting Person
CO

CUSIP No. 690370101

13G

1

Names of Reporting Person/I.R.S. Identification Nos. of Above Persons (Entities Only)
FFHL GROUP LTD.

2

Check the Appropriate Box if a Member of a Group

(a)

o

(b)

x

3

SEC Use Only

4

Citizenship or Place of Organization
CANADA

Number of
Shares
Beneficially
Owned by
Each
Reporting
Person With

5

Sole Voting Power

6

Shared Voting Power
2,930,858

7

Sole Dispositive Power

8

Shared Dispositive Power
2,930,858

9

Aggregate Amount Beneficially Owned by Each Reporting Person
2,930,858

10

Check Box if the Aggregate Amount in Row (9) Excludes Certain Shares  o

11

Percent of Class Represented by Amount in Row 9
11.6%

12

Type of Reporting Person
CO

CUSIP No. 690370101

13G

1

Names of Reporting Person/I.R.S. Identification Nos. of Above Persons (Entities Only)
FAIRFAX (US) INC.

2

Check the Appropriate Box if a Member of a Group

(a)

o

(b)

x

3

SEC Use Only

4

Citizenship or Place of Organization
DELAWARE

Number of
Shares
Beneficially
Owned by
Each
Reporting
Person With

5

Sole Voting Power

6

Shared Voting Power
3,184,677

7

Sole Dispositive Power

8

Shared Dispositive Power
3,184,677

9

Aggregate Amount Beneficially Owned by Each Reporting Person
3,184,677

10

Check Box if the Aggregate Amount in Row (9) Excludes Certain Shares  o

11

Percent of Class Represented by Amount in Row 9
12.6%

12

Type of Reporting Person
CO

CUSIP No. 690370101

13G

1

Names of Reporting Person/I.R.S. Identification Nos. of Above Persons (Entities Only)
ODYSSEY US HOLDINGS INC.

2

Check the Appropriate Box if a Member of a Group

(a)

o

(b)

x

3

SEC Use Only

4

Citizenship or Place of Organization
DELAWARE

Number of
Shares
Beneficially
Owned by
Each
Reporting
Person With

5

Sole Voting Power

6

Shared Voting Power
981,300

7

Sole Dispositive Power

8

Shared Dispositive Power
981,300

9

Aggregate Amount Beneficially Owned by Each Reporting Person
981,300

10

Check Box if the Aggregate Amount in Row (9) Excludes Certain Shares  o

11

Percent of Class Represented by Amount in Row 9
3.9%

12

Type of Reporting Person
CO

CUSIP No. 690370101

13G

1

Names of Reporting Person/I.R.S. Identification Nos. of Above Persons (Entities Only)
ODYSSEY RE HOLDINGS CORP.

2

Check the Appropriate Box if a Member of a Group

(a)

o

(b)

x

3

SEC Use Only

4

Citizenship or Place of Organization
DELAWARE

Number of
Shares
Beneficially
Owned by
Each
Reporting
Person With

5

Sole Voting Power

6

Shared Voting Power
981,300

7

Sole Dispositive Power

8

Shared Dispositive Power
981,300

9

Aggregate Amount Beneficially Owned by Each Reporting Person
981,300

10

Check Box if the Aggregate Amount in Row (9) Excludes Certain Shares  o

11

Percent of Class Represented by Amount in Row 9
3.9%

12

Type of Reporting Person
CO

CUSIP No. 690370101

13G

1

Names of Reporting Person/I.R.S. Identification Nos. of Above Persons (Entities Only)
ODYSSEY REINSURANCE COMPANY

2

Check the Appropriate Box if a Member of a Group

(a)

o

(b)

x

3

SEC Use Only

4

Citizenship or Place of Organization
CONNECTICUT

Number of
Shares
Beneficially
Owned by
Each
Reporting
Person With

5

Sole Voting Power

6

Shared Voting Power
981,300

7

Sole Dispositive Power

8

Shared Dispositive Power
981,300

9

Aggregate Amount Beneficially Owned by Each Reporting Person
981,300

10

Check Box if the Aggregate Amount in Row (9) Excludes Certain Shares  o

11

Percent of Class Represented by Amount in Row 9
3.9%

12

Type of Reporting Person
CO

CUSIP No. 690370101

13G

1

Names of Reporting Person/I.R.S. Identification Nos. of Above Persons (Entities Only)
CLEARWATER SELECT INSURANCE COMPANY

2

Check the Appropriate Box if a Member of a Group

(a)

o

(b)

x

3

SEC Use Only

4

Citizenship or Place of Organization
CONNECTICUT

Number of
Shares
Beneficially
Owned by
Each
Reporting
Person With

5

Sole Voting Power

6

Shared Voting Power
981,300

7

Sole Dispositive Power

8

Shared Dispositive Power
981,300

9

Aggregate Amount Beneficially Owned by Each Reporting Person
981,300

10

Check Box if the Aggregate Amount in Row (9) Excludes Certain Shares  o

11

Percent of Class Represented by Amount in Row 9
3.9%

12

Type of Reporting Person
CO

CUSIP No. 690370101

13G

1

Names of Reporting Person/I.R.S. Identification Nos. of Above Persons (Entities Only)
CRUM & FORSTER HOLDINGS CORP.

2

Check the Appropriate Box if a Member of a Group

(a)

o

(b)

x

3

SEC Use Only

4

Citizenship or Place of Organization
DELAWARE

Number of
Shares
Beneficially
Owned by
Each
Reporting
Person With

5

Sole Voting Power

6

Shared Voting Power
1,730,524

7

Sole Dispositive Power

8

Shared Dispositive Power
1,730,524

9

Aggregate Amount Beneficially Owned by Each Reporting Person
1,730,524

10

Check Box if the Aggregate Amount in Row (9) Excludes Certain Shares  o

11

Percent of Class Represented by Amount in Row 9
6.8%

12

Type of Reporting Person
CO

CUSIP No. 690370101

13G

1

Names of Reporting Person/I.R.S. Identification Nos. of Above Persons (Entities Only)
UNITED STATES FIRE INSURANCE COMPANY

2

Check the Appropriate Box if a Member of a Group

(a)

o

(b)

x

3

SEC Use Only

4

Citizenship or Place of Organization
DELAWARE

Number of
Shares
Beneficially
Owned by
Each
Reporting
Person With

5

Sole Voting Power

6

Shared Voting Power
1,730,524

7

Sole Dispositive Power

8

Shared Dispositive Power
1,730,524

9

Aggregate Amount Beneficially Owned by Each Reporting Person
1,730,524

10

Check Box if the Aggregate Amount in Row (9) Excludes Certain Shares  o

11

Percent of Class Represented by Amount in Row 9
6.8%

12

Type of Reporting Person
CO

CUSIP No. 690370101

13G

1

Names of Reporting Person/I.R.S. Identification Nos. of Above Persons (Entities Only)
TIG HOLDINGS, INC.

2

Check the Appropriate Box if a Member of a Group

(a)

o

(b)

x

3

SEC Use Only

4

Citizenship or Place of Organization
DELAWARE

Number of
Shares
Beneficially
Owned by
Each
Reporting
Person With

5

Sole Voting Power

6

Shared Voting Power
472,853

7

Sole Dispositive Power

8

Shared Dispositive Power
472,853

9

Aggregate Amount Beneficially Owned by Each Reporting Person
472,853

10

Check Box if the Aggregate Amount in Row (9) Excludes Certain Shares  o

11

Percent of Class Represented by Amount in Row 9
1.9%

12

Type of Reporting Person
CO

CUSIP No. 690370101

13G

1

Names of Reporting Person/I.R.S. Identification Nos. of Above Persons (Entities Only)
TIG INSURANCE COMPANY

2

Check the Appropriate Box if a Member of a Group

(a)

o

(b)

x

3

SEC Use Only

4

Citizenship or Place of Organization
CALIFORNIA

Number of
Shares
Beneficially
Owned by
Each
Reporting
Person With

5

Sole Voting Power

6

Shared Voting Power
472,853

7

Sole Dispositive Power

8

Shared Dispositive Power
472,853

9

Aggregate Amount Beneficially Owned by Each Reporting Person
472,853

10

Check Box if the Aggregate Amount in Row (9) Excludes Certain Shares  o

11

Percent of Class Represented by Amount in Row 9
1.9%

12

Type of Reporting Person
CO

Item 1. (a)

Name of Issuer:
Overstock.com, Inc.

Item 1(b)

Address of Issuer’s Principal Executive Offices:
6350 South 3000 East, Salt Lake City, Utah, 84121

Item 2. (a)

Name of Person Filing:
This statement is being jointly filed by the following persons (collectively, the “Reporting Persons”):

1.     V. Prem Watsa, an individual;

2.     1109519 Ontario Limited (“1109519”), a corporation incorporated under the laws of Ontario;

3.     The Sixty Two Investment Company Limited (“Sixty Two”), a corporation incorporated under the laws of British Columbia;

4.     810679 Ontario Limited (“810679”), a corporation incorporated under the laws of Ontario;

5.     Fairfax Financial Holdings Limited (“Fairfax”), a corporation incorporated under the laws of Canada;

6.     FFHL Group Ltd. (“FFHL”), a corporation incorporated under the laws of Canada;

7.     Fairfax (US) Inc. (“Fairfax US”), a corporation incorporated under the laws of Delaware;

8.     Odyssey US Holdings Inc. (“Odyssey US”), a corporation incorporated under the laws of Delaware;

9.     Odyssey Re Holdings Corp. (“Odyssey Re”), a corporation incorporated under the laws of Delaware;

10.  Odyssey Reinsurance Company (“Odyssey”), a corporation incorporated under the laws of Connecticut;

11.  Clearwater Select Insurance Company (“Clearwater”), a corporation incorporated under the laws of Connecticut;

12.  Crum & Forster Holdings Corp. (“Crum & Forster”), a corporation incorporated under the laws of Delaware;

13.  United States Fire Insurance Company (“US Fire”), a corporation incorporated under the laws of Delaware;

14.  TIG Holdings, Inc. (“TIGH”), a corporation incorporated under the laws of Delaware; and

15.  TIG Insurance Company (“TIG”), a corporation incorporated under the laws of California.

Item 2(b)

Address of Principal Business Office:
The addresses of the Reporting Persons are as follows:

1.     Mr. Watsa’s business address is 95 Wellington Street West, Suite 800, Toronto, Ontario M5J 2N7;

2.     The principal business address and principal office address of 1109519 is 95 Wellington Street West, Suite 800, Toronto, Ontario M5J 2N7;

3.     The principal business address and principal office address of Sixty Two is 1600 Cathedral Place, 925 West Georgia Street, Vancouver, British Columbia V6C 3L3;

4.     The principal business address and principal office address of 810679 is 95 Wellington Street West, Suite 800, Toronto, Ontario M5J 2N7;

5.     The principal business address and principal office address of Fairfax is 95 Wellington Street West, Suite 800, Toronto, Ontario M5J 2N7;

6.     The principal business address and principal office address of FFHL is 95 Wellington Street West, Suite 800, Toronto, Ontario M5J 2N7;

7.     The principal business address and principal office address of Fairfax US is 2850 Lake Vista Drive, Suite 150, Lewisville, Texas 75067;

8.     The principal business address and principal office address of Odyssey US is 300 First Stamford Place, Stamford, Connecticut 06902;

9.     The principal business address and principal office address of Odyssey Re is 300 First Stamford Place, Stamford, Connecticut 06902;

10.  The principal business address and principal office address of Odyssey is 300 First Stamford Place, Stamford, Connecticut 06902;

11.  The principal business address and principal office address of Clearwater is 300 First Stamford Place, Stamford, Connecticut 06902;

12.  The principal business address and principal office address of Crum & Forster is 305 Madison Avenue, Morristown, New Jersey 07962;

13.  The principal business address and principal office address of US Fire is 305 Madison Avenue, Morristown, New Jersey 07962;

14.  The principal business address and principal office address of TIGH is 250 Commercial Street, Suite 5000, Manchester, New Hampshire 03101; and

15.  The principal business address and principal office address of TIG is 250 Commercial Street, Suite 5000, Manchester, New Hampshire 03101.

Item 2(c)

Citizenship:
V. Prem Watsa is a citizen of Canada.

Item 2(d)

Title of Class of Securities:
Common Stock

Item 2(e)

CUSIP Number:
690370101

Item 3.

If this statement is filed pursuant to Rule 13d-1(b) or 13d-2(b) or (c), check whether the person filing is a:

(a)

o

Broker or dealer registered under section 15 of the Act (15 U.S.C. 78o);

(b)

o

Bank as defined in section 3(a)(6) of the Act (15 U.S.C. 78c);

(c)

o

Insurance company as defined in section 3(a)(19) of the Act (15 U.S.C. 78c);

(d)

o

Investment company registered under section 8 of the Investment Company Act of 1940 (15 U.S.C. 80a-8);

(e)

o

An investment adviser in accordance with §240.13d-1(b)(1)(ii)(E);

(f)

o

An employee benefit plan or endowment fund in accordance with §240.13d-1(b)(1)(ii)(F);

(g)

o

A parent holding company or control person, in accordance with §240.13d-1(b)(1)(ii)(G);

(h)

o

A savings association as defined in Section 3(b) of the Federal Deposit Insurance Act (12 U.S.C. 1813);

(i)

o

A church plan that is excluded from the definition of an investment company under section 3(c)(14) of the Investment Company Act of 1940 (15 U.S.C. 80a-3);

(j)

o

A non-US institution in accordance with §240.13d-1(b)(1)(ii)(J);

(k)

x

Group, in accordance with §240.13d-1(b)(1)(ii)(K).

Item 4.

Ownership.

Based on the most recent information available, the aggregate number and percentage of the shares of common stock (the “Shares”) of Overstock.com, Inc. (“Overstock”) that are beneficially owned by each of the Reporting Persons is set forth in boxes 9 and 11 of the second part of the cover page to this Schedule 13G/A, and such information is incorporated herein by reference.

The number of Shares as to which each of the Reporting Persons has sole voting power, shared voting power, sole dispositive power and shared dispositive power is set forth in boxes 5, 6, 7 and 8, respectively, on the second part of the cover page to this Schedule 13G/A, and such information is incorporated herein by reference.

Neither the filing of this Schedule 13G/A nor the information contained herein shall be deemed to constitute an affirmation by V. Prem Watsa, 1109519, Sixty Two, 810679, Fairfax, FFHL, Fairfax US, Odyssey US, Odyssey Re, Odyssey, Clearwater, Crum & Forster, US Fire, TIGH or TIG that such person is the beneficial owner of the Shares referred to

herein for purposes of Section 13(d) or 13(g) of the Securities Exchange Act of 1934, as amended, or for any other purpose, and such beneficial ownership is expressly disclaimed.

Item 5.

Ownership of Five Percent or Less of a Class.

Not applicable.

Item 6.

Ownership of More than Five Percent on Behalf of Another Person.

Not applicable.

Item 7.

Identification and Classification of the Subsidiary Which Acquired the Security Being Reported on By the Parent Holding Company.

Not applicable.

Item 8.

Identification and Classification of Members of the Group.

See attached Exhibit No. 1.

Item 9.

Notice of Dissolution of Group.

Not applicable.

Item 10.

Certification.

By signing below I certify that, to the best of my knowledge and belief, the securities referred to above were acquired and are held in the ordinary course of business and were not acquired and are not held for the purpose of or with the effect of changing or influencing control of the issuer of the securities and were not acquired and are not held in connection with or as a participant in any transaction having that purpose or effect.

Dated: May 19, 2016

V. Prem Watsa

/s/ V. Prem Watsa

Dated: May 19, 2016

1109519 Ontario Limited

By:

/s/ V. Prem Watsa

Name: V. Prem Watsa

Title: President

Dated: May 19, 2016

The Sixty Two Investment Company Limited

By:

/s/ V. Prem Watsa

Name: V. Prem Watsa

Title: President

Dated: May 19, 2016

810679 Ontario Limited

By:

/s/ V. Prem Watsa

Name: V. Prem Watsa

Title: President

Dated: May 19, 2016

Fairfax Financial Holdings Limited

By:

/s/ Paul Rivett

Name: Paul Rivett

Title: President

Dated: May 19, 2016

FFHL Group Ltd.

By:

/s/ Paul Rivett

Name: Paul Rivett

Title: Director

Dated: May 19, 2016

Fairfax (US) Inc.

By:

/s/ Dorothy D. Whitaker

Name: Dorothy D. Whitaker

Title: Vice President, Treasurer, Secretary and Director

Dated: May 19, 2016

Odyssey US Holdings Inc.

By:

/s/ Jan Christiansen

Name: Jan Christiansen

Title: Executive Vice President

Dated: May 19, 2016

Odyssey Re Holdings Corp.

By:

/s/ Jan Christiansen

Name: Jan Christiansen

Title: Executive Vice President

Dated: May 19, 2016

Odyssey Reinsurance Company

By:

/s/ Kirk M. Reische

Name: Kirk M. Reische

Title: Vice President

Dated: May 19, 2016

Clearwater Select Insurance Company

By:

/s/ Kirk M. Reische

Name:

Kirk M. Reische

Title:

Vice President

Dated: May 19, 2016

Crum & Forster Holdings Corp.

By:

/s/ Paul W. Bassaline

Name:

Paul W. Bassaline

Title:

Senior Vice President, Chief Financial Officer, Treasurer and Director

Dated: May 19, 2016

United States Fire Insurance Company

By:

/s/ Paul W. Bassaline

Name:

Paul W. Bassaline

Title:

Senior Vice President, Chief Financial Officer and Director

Dated: May 19, 2016

TIG Holdings, Inc.

By:

/s/ Dorothy D. Whitaker

Name:

Dorothy D. Whitaker

Title:

Chairman, President, Secretary and Director

Dated: May 19, 2016

TIG Insurance Company

By:

/s/ Deborah A. Irving

Name:

Deborah A. Irving

Title:

Director, Senior Vice President, Chief Financial Officer and Treasurer

Exhibit No.

Description

1

Members of filing group.

2

Joint Filing Agreement dated as of May 19, 2016 among V. Prem Watsa, 1109519 Ontario Limited, The Sixty Two Investment Company Limited, 810679 Ontario Limited, Fairfax Financial Holdings Limited, FFHL Group Ltd., Fairfax (US) Inc., Odyssey US Holdings Inc., Odyssey Re Holdings Corp., Odyssey Reinsurance Company, Clearwater Select Insurance Company, Crum & Forster Holdings Corp., United States Fire Insurance Company, TIG Holdings, Inc. and TIG Insurance Company.