| 1 | Ascension Welfare Benefits Trust Saint Louis | $915.1M | $191.4M | $172.4M |
| 2 | Ascension Health Professional and General Liability Self-insurance Saint Louis | $335.9M | $335.9M | $821.7M |
| 3 | Missouri Chamber Federation Benefit Plan Trust Jefferson Cty | $228.5M | $228.5M | $24.5M |
| 4 | Ameren Active Employee Healthcare Tr Saint Louis | $164.6M | $164.6M | $15.4M |
| 5 | Ozark Schools Benefits Association Bolivar | $123.9M | $123.9M | $25.9M |
| 6 | Ssmhcs Liability Trust Mercantile Bank Ttee Saint Louis | $51.4M | $51.4M | $205.1M |
| 7 | Learfield Communications Group Benefit Trust INC Jefferson Cty | $24.8M | $24.8M | $2.1M |
| 8 | St. Louis Labor Healthcare Network Saint Louis | $17.9M | $14.6M | $51.0M |
| 9 | Ufcw Union Local No 88 Employers Health & Welfare Fund St. Louis | $17.1M | $17.1M | $21.5M |
| 10 | Government Employees Health Association INC Voluntary Welfare Lees Summit | $13.8M | $13.8M | $2.9M |
| 11 | Alton Ibew-neca Health & Welfare Pl Saint Louis | $6.5M | $6.5M | $7.5M |
| 12 | Moneta Group Employee Benefit Plan Tr Saint Louis | $6.3M | $6.3M | $4.0M |
| 13 | Unite Here Local 74 Welfare and Dental Trust St. Louis | $3.6M | $3.2M | $1.1M |
| 14 | Boilermakers Local 83 Supplemental Health and Welfare Fund Kansas City | $3.4M | $917K | $13.7M |
| 15 | Hallmark Retiree Veba Tr Kansas City | $2.7M | $2.7M | $5.9M |
| 16 | National Agricultural Genotyping Center INC Saint Louis | $2.3M | $2.3M | $1.7M |
| 17 | Fraternal Order of Eagles Poplar Bluff | $1.9M | $1.9M | $61K |
| 18 | Carrollton Oak Hill Cemetery Association Carrollton | $1.9M | $872K | $2.3M |
| 19 | Orscheln Industries Health Plan Moberly | $1.5M | $1.5M | $1.3M |
| 20 | Cottleville Fire Protection District Veba Health Savings Trust Saint Charles | $1.1M | $1.1M | $6.0M |
| 21 | Meramec Valley Aerie 3781 Fraternal Order of Eagles Sullivan | $1.0M | $803K | $581K |
| 22 | Phi Mu Fraternity Columbia | $979K | $979K | $2.4M |
| 23 | Benevolent & Protective Order of Elks of the USA Farmington | $899K | $677K | $592K |
| 24 | Peabody Investments Corp Non-represented Retiree Veba Tr Saint Louis | $891K | $891K | $11.3M |
| 25 | Benevolent & Protective Order of Elks of the USA Gladstone | $861K | $281K | $519K |
| 26 | Midwest Multistate Division Service Corporation Jefferson Cty | $809K | $809K | $339K |
| 27 | Delta XI Bldg Corp of Delta Delta Delta Columbia | $798K | $798K | $5.4M |
| 28 | Fraternal Order of Eagles Poplar Bluff | $746K | $53K | $85K |
| 29 | Missouri Water Association Camdenton | $724K | $724K | $1.6M |
| 30 | Blue Springs Cemetery Association INC Blue Springs | $676K | $675K | $3.4M |
| 31 | Board of Police Commissioners of Kansas City Missouri Post Emplo Tr Kansas City | $662K | $662K | $2.7M |
| 32 | Theta Chi Fraternity University of Missouri Iota Mu Chapter Columbia | $609K | $609K | $25K |
| 33 | Benevolent and Protective Order of Elks of the USA Sikeston | $577K | $459K | $920K |
| 34 | Local 649 Sub and Welfare Fund Saint Louis | $534K | $534K | $8.9M |
| 35 | James C Stewart Charitable Foundation Saint Louis | $496K | $0 | $1.4M |
| 36 | Fraternal Order of Eagles Saint Joseph | $474K | $273K | $1.1M |
| 37 | Robertson Fire Protection District Veba Health Savings Trust Hazelwood | $449K | $348K | $985K |
| 38 | Ibew-neca Income Security Fund Saint Louis | $431K | $431K | $4.2M |
| 39 | Queen City Roofing & Contracting Co Veba Springfield | $409K | $409K | $526K |
| 40 | Osage County Mutual Aid Association Koeltztown | $392K | $392K | $2.2M |
| 41 | River Hills Aerie No 4034 Fraternal Order of Eagles Perryville | $386K | $211K | $785K |
| 42 | Ypo Pacific Star INC Springfield | $385K | $385K | $137K |
| 43 | Masonic Temple Charitable Trust Saint Louis | $374K | $0 | $675K |
| 44 | Mount Hope Cemetery Webb City | $369K | $369K | $301K |
| 45 | Iota Mu Chapter of Theta Chi Fraternity Alumni Corporation Saint Charles | $352K | $114K | $3.7M |
| 46 | Vikings USA Boothel Mo Poplar Bluff | $337K | $183K | $60K |
| 47 | Delta Chi Fraternity Columbia | $336K | $336K | $22 |
| 48 | Fraternal Order of Police Independence | $312K | $304K | $468K |
| 49 | Maple Park Cemetery Association Springfield | $312K | $252K | $316K |
| 50 | United Cemetery Association INC Saint Louis | $303K | $303K | $33K |