| 1 | The Commonwealth of Massachusetts · Boston | State and local governments | 590 | $78 billion |
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| 2 | Massachusetts Department of Elementary & Secondary Education · Everett | State and local governments | 180 | $9.1 billion |
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| 3 | Massachusetts Department of Transportation · Boston | State and local governments | 1,670 | $4.8 billion |
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| 4 | Massachusetts Bay Transportation Authority · Boston | State and local governments | 61 | $4.0 billion |
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| 5 | Emergency Management Agency Massachusetts · Framingham | State and local governments | 60 | $3.6 billion |
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| 6 | Department of Transitional Assistan · Boston | State and local governments | 24 | $3.2 billion |
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| 7 | The General Hospital Corporation · Boston | Nonprofits | 2,205 | $3.0 billion |
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| 8 | Massachusetts Department of Public Health · Boston | State and local governments | 261 | $2.5 billion |
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| 9 | Brigham & Womens Hospital Inc · Boston | Nonprofits | 1,359 | $2.0 billion |
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| 10 | Massachusetts Institute of Technology · Cambridge | Colleges and universities | 2,000 | $2.0 billion |
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| 11 | Executive Office of Housing and Livable Communities · Boston | State and local governments | 313 | $1.8 billion |
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| 12 | Massachusetts Department of Early Education & Care · Boston | State and local governments | 18 | $1.6 billion |
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| 13 | The Children's Hospital Corporation · Boston | Nonprofits | 877 | $1.3 billion |
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| 14 | Commonwealth of Massachusetts Dept of Children & Families · Boston | State and local governments | 75 | $1.1 billion |
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| 15 | University of Massachusetts Medical School · Worcester | Colleges and universities | 792 | $1.1 billion |
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| 16 | Massachusetts Clean Water Trust · Boston | State and local governments | 34 | $1.0 billion |
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| 17 | Woods Hole Oceanographic Institution · Woods Hole | Colleges and universities | 606 | $962 million |
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| 18 | Trustees of Boston University · Boston | Colleges and universities | 644 | $922 million |
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| 19 | Dana-Farber Cancer Institute, Inc. · Boston | Nonprofits | 544 | $908 million |
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| 20 | President and Fellows of Harvard College · Cambridge | Colleges and universities | 953 | $899 million |
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| 21 | President and Fellows of Harvard College · Boston | Colleges and universities | 777 | $890 million |
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| 22 | Executive Office of Labor & Wo · Boston | State and local governments | 90 | $860 million |
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| 23 | Jsi Research & Training Institute Inc · Boston | Nonprofits | 63 | $855 million |
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| 24 | Massachusetts Department of Energy Resources · Boston | State and local governments | 19 | $797 million |
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| 25 | Trustees of Boston University · Boston | Colleges and universities | 993 | $756 million |
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| 26 | Northeastern University · Boston | Colleges and universities | 909 | $729 million |
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| 27 | President and Fellows of Harvard College · Boston | Colleges and universities | 352 | $711 million |
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| 28 | University of Massachusetts Lowell · Amherst | Colleges and universities | 984 | $709 million |
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| 29 | Beth Israel Deaconess Medical Center, Inc. · Boston | Nonprofits | 486 | $702 million |
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| 30 | The Broad Institute, Inc · Cambridge | Nonprofits | 226 | $589 million |
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| 31 | Boston Housing Authority · Boston | State and local governments | 413 | $568 million |
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| 32 | Massachusetts Port Authority · East Boston | State and local governments | 60 | $535 million |
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| 33 | Trustees of Tufts College · Boston | Colleges and universities | 355 | $466 million |
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| 34 | Boston, City of · Boston | State and local governments | 230 | $391 million |
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| 35 | Global Life Sciences Solutions USA LLC · Marlborough | Businesses | 2 | $328 million |
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| 36 | Ascend Elements, Inc. · Westborough | Small businesses | 2 | $319 million |
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| 37 | Education Development Center, Inc. · Waltham | Nonprofits | 70 | $314 million |
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| 38 | Commonwealth of Massachusetts Military Division · Hanscom Afb | State and local governments | 80 | $293 million |
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| 39 | Massability · Boston | State and local governments | 39 | $270 million |
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| 40 | Department of Public Safety · Boston | State and local governments | 119 | $260 million |
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| 41 | Veterans' Home in Holyoke · Holyoke | State and local governments | 6 | $251 million |
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| 42 | Massachusetts Executive Office of Aging and Independence · Boston | State and local governments | 83 | $239 million |
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| 43 | University of Massachusetts Lowell · Lowell | Colleges and universities | 298 | $216 million |
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| 44 | University of Mass at Boston · Dorchester | Colleges and universities | 214 | $214 million |
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| 45 | Trustees of Boston College · Chestnut Hill | Colleges and universities | 288 | $213 million |
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| 46 | Brandeis University · Waltham | Colleges and universities | 213 | $210 million |
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| 47 | Trustees of Tufts College · Somerville | Colleges and universities | 328 | $209 million |
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| 48 | Massachusetts Department of Environmental Protection · Boston | State and local governments | 50 | $206 million |
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| 49 | Boston Medical Center Corporation · Boston | Nonprofits | 167 | $202 million |
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| 50 | Action for Boston Community Development, Inc · Boston | Nonprofits | 11 | $200 million |
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| 51 | The McLean Hospital Corporation · Belmont | Nonprofits | 140 | $193 million |
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| 52 | Massachusetts Eye and Ear Infirmary · Boston | Nonprofits | 115 | $189 million |
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| 53 | Massachusetts Cultural Council · Boston | State and local governments | 7 | $182 million |
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| 54 | Cape Cod Regional Transit Auth · Hyannis | Other | 13 | $178 million |
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| 55 | Boston, City of · Boston | State and local governments | 61 | $158 million |
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| 56 | Worcester Polytechnic Institute · Worcester | Colleges and universities | 260 | $151 million |
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| 57 | Form Factory 1, LLC · Somerville | Businesses | 1 | $150 million |
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| 58 | Pioneer Valley Transit Authority · Springfield | Other | 16 | $147 million |
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| 59 | Boston Public Health Commission · Boston | State and local governments | 25 | $140 million |
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| 60 | Massachusetts Department of Mental Health · Boston | State and local governments | 24 | $131 million |
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| 61 | Tufts Medical Center Parent, Inc. · Boston | Nonprofits | 89 | $126 million |
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| 62 | Highland CSB 1, LLC · Beverly | Businesses | 5 | $124 million |
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| 63 | Commonwealth of Massachusetts · Boston | State and local governments | 7 | $124 million |
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| 64 | Worcester Housing Authority · Worcester | Tribal governments and organizations | 105 | $123 million |
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| 65 | Worcester Regional Transit Authority · Worcester | Other | 10 | $116 million |
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| 66 | National Bureau of Economic Research Inc · Cambridge | Nonprofits | 123 | $111 million |
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| 67 | Joslin Diabetes Center, Inc. · Boston | Nonprofits | 62 | $104 million |
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| 68 | Harvard Pilgrim Health Care, Inc. · Canton | Nonprofits | 63 | $104 million |
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| 69 | Orsted Star P2X LLC · Boston | Businesses | 1 | $99.0 million |
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| 70 | Sublime Systems, Inc. · Somerville | Small businesses | 4 | $97.7 million |
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| 71 | Smithsonian Institution · Cambridge | Nonprofits | 193 | $96.8 million |
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| 72 | New England Interstate Water Pollution Control Commission · Lowell | Nonprofits | 30 | $96.3 million |
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| 73 | Commonwealth of Massachusetts Executive Office of Health and Human Services · Boston | State and local governments | 7 | $95.1 million |
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| 74 | City of Worcester · Worcester | State and local governments | 47 | $92.4 million |
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| 75 | Mineral Basin Solar Power, LLC · Boston | Businesses | 1 | $90.0 million |
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| 76 | City Year, Inc. · Boston | Nonprofits | 2 | $87.1 million |
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| 77 | Springfield Housing Authority · Springfield | State and local governments | 74 | $86.6 million |
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| 78 | Massachusetts Service Alliance, Inc · Boston | State and local governments | 20 | $86.5 million |
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| 79 | Holyoke.chicopee.springfield Head Start, Inc. · Springfield | Nonprofits | 6 | $86.0 million |
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| 80 | The Schepens Eye Research Institute, Inc. · Boston | Nonprofits | 76 | $85.4 million |
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| 81 | University of Massachusetts Dartmouth · North Dartmouth | Colleges and universities | 116 | $84.8 million |
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| 82 | New Bedford Housing Authority · New Bedford | State and local governments | 64 | $82.6 million |
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| 83 | City of Springfield · Springfield | State and local governments | 37 | $82.2 million |
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| 84 | Fall River Housing Authority · Fall River | State and local governments | 78 | $81.8 million |
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| 85 | Soldier on, Inc · Pittsfield | Nonprofits | 13 | $79.2 million |
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| 86 | Lowell Housing Authority · Lowell | State and local governments | 39 | $77.5 million |
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| 87 | Brockton Housing Authority · Brockton | Tribal governments and organizations | 22 | $74.6 million |
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| 88 | Massachusetts Office of Executive Education · Boston | State and local governments | 3 | $71.7 million |
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| 89 | Health Resources in Action, Inc. · Boston | Nonprofits | 16 | $70.8 million |
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| 90 | The Marine Biological Laboratory · Woods Hole | Nonprofits | 82 | $69.9 million |
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| 91 | Commonwealth of Massachusetts Dept. of Conservation & Recreation · Boston | State and local governments | 75 | $69.5 million |
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| 92 | Jobs for the Future, Inc · Boston | Nonprofits | 11 | $69.0 million |
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| 93 | Southeastern Regional Transit Authority · New Bedford | Other | 20 | $67.3 million |
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| 94 | Neighborhealth Corporation · East Boston | Nonprofits | 12 | $65.1 million |
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| 95 | Bunker Hill Community College · Charlestown | Colleges and universities | 10 | $65.0 million |
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| 96 | State Police Department · Framingham | State and local governments | 37 | $64.2 million |
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| 97 | Community Action Pioneer Valley, Inc. · Greenfield | Nonprofits | 91 | $64.1 million |
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| 98 | Merrimack Valley Regional Transit Authority · Haverhill | Other | 15 | $63.3 million |
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| 99 | Lawrence F Quigley Memorial Hospital Inc · Chelsea | State and local governments | 5 | $62.2 million |
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| 100 | City of Cambridge · Cambridge | State and local governments | 109 | $60.8 million |
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