| 1 | Aurora Health Care INC Milwaukee | $7.4B | $7.4B | $8.0B |
| 2 | Security Health Plan of Wisconsin INC Marshfield | $1.6B | $1.5B | $393.6M |
| 3 | Delta Dental of Wisconsin INC Stevens Point | $1.0B | $984.0M | $397.5M |
| 4 | Wisconsin Counties Association Group Health Tr Madison | $681.1M | $331.4M | $139.6M |
| 5 | Quartz Health Plan Corporation Fitchburg | $492.3M | $477.3M | $129.1M |
| 6 | Dairyland Power Cooperative La Crosse | $485.8M | $485.8M | $1.6B |
| 7 | Trusted Fraternal Life Milwaukee | $358.0M | $162.8M | $1.9B |
| 8 | Operating Engineers Local 139 Pewaukee | $348.0M | $196.2M | $529.7M |
| 9 | Wisconsin Laborers Health Fund Deforest | $324.6M | $124.2M | $359.9M |
| 10 | Wea Insurance Corporation Madison | $294.8M | $22.4M | $552.1M |
| 11 | Wisconsin Compensation Rating Bureau as Trustees for Claimants Waukesha | $286.1M | $72.6M | $250.6M |
| 12 | Prohealth Care INC Wauxesna | $193.3M | $181.9M | $2.0B |
| 13 | Wisconsin Public Service Corporation Master Welfare Benefit Milwaukee | $179.5M | $29.7M | $287.3M |
| 14 | Wisconsin Electrical Employees Benefits Funds LLC Madison | $152.3M | $112.2M | $227.4M |
| 15 | Ball State University Health Care Plan Milwaukee | $130.2M | $28.3M | $344.0M |
| 16 | Telephone and Data Systems INC Employees Benefit Trust Madison | $125.7M | $125.5M | $13.1M |
| 17 | St. Marys Hospital of Superior Superior | $123.2M | $113.2M | $211.6M |
| 18 | Wisconsin Pipe Trades Health Fund Milwaukee | $121.9M | $47.6M | $54.5M |
| 19 | International Childrens Fund INC Neenah | $119.0M | $119.0M | $16.5M |
| 20 | Agrace Hospicecare Incorporated Fitchburg | $117.6M | $116.7M | $16.6M |
| 21 | Peoples Energy Corporation Life and Health Benefits Trust Milwaukee | $117.2M | $21.3M | $194.6M |
| 22 | Wisconsin Health Fund Milwaukee | $115.9M | $31.3M | $93.6M |
| 23 | Adams-columbia Electric Co-op Friendship | $89.4M | $85.0M | $261.8M |
| 24 | Medical College of Wisconson Affiliated Hospitals INC Milwaukee | $87.4M | $87.4M | $5.9M |
| 25 | Milwaukee Drivers Health & Welfare Trust Fund Milwaukee | $83.7M | $76.4M | $74.5M |
| 26 | Wisconsin Sheet Metal Health and Benefit Trust Fund Waukesha | $75.3M | $58.6M | $56.8M |
| 27 | Electrical Construction Industry Prefunding Credit Reimbursement Pr Wauwatosa | $75.2M | $5.3M | $69.0M |
| 28 | The Lakes Community Health Center INC Iron River | $72.0M | $67.9M | $48.8M |
| 29 | Wisconsin Lutheran College Milwaukee | $67.1M | $56.3M | $138.0M |
| 30 | Childrens Service Society of Wisconsin Milwaukee | $66.9M | $66.9M | $15.7M |
| 31 | Interstate Power and Light Non-bargaining Employees Health Madison | $66.6M | $11.0M | $59.2M |
| 32 | Rock County Electric Cooperative Association Janesville | $66.4M | $66.3M | $131.5M |
| 33 | Sixteenth Street Community Health Centers INC Milwaukee | $64.5M | $64.3M | $44.2M |
| 34 | Betterlife Madison | $63.5M | $63.5M | $586.6M |
| 35 | Milwaukee Electrical Industry Vacation - Holiday Plan Wauwatosa | $63.1M | $18.9M | $20.7M |
| 36 | Milwaukee Painters Local Union No 781 Welfare Fund Milwaukee | $57.1M | $14.0M | $34.5M |
| 37 | Bader Philanthropies INC Milwaukee | $55.9M | $0 | $27.6M |
| 38 | Mount Mary University INC Milwaukee | $55.4M | $40.5M | $73.3M |
| 39 | Argosy Foundation Milwaukee | $54.1M | $0 | $74.0M |
| 40 | Associated Banc-corp Group Health Employee Benefit Plan and Trust Green Bay | $51.2M | $51.2M | $2.9M |
| 41 | Access Community Health Centers INC Madison | $50.3M | $45.6M | $32.7M |
| 42 | Opportunities INC of Jefferson County Fort Atkinson | $49.3M | $20.9M | $96.8M |
| 43 | Oakdale Electric Cooperative Oakdale | $48.5M | $48.3M | $123.7M |
| 44 | Greater Wisconsin Agency on Aging Resources INC Madison | $47.2M | $47.2M | $13.9M |
| 45 | Theodore W Batterman Family Foundation INC Milwaukee | $47.2M | $0 | $57.2M |
| 46 | Riverland Energy Cooperative Arcadia | $46.5M | $46.5M | $133.7M |
| 47 | William F Vilas Estate Oregon | $45.8M | $8.7M | $135.6M |
| 48 | Sonnentag Foundation Ltd Marathon | $45.4M | $0 | $45.3M |
| 49 | Richard and Ethel Herzfeld Foundation INC Milwaukee | $44.9M | $0 | $81.5M |
| 50 | Bethany Lutheran Homes INC La Crosse | $44.7M | $44.7M | $112.0M |