| Haddow Communications | MD | 20021016 | $1.1M | Media Fees |
| Malchow, Schlackman, Hoppey & Cooper | DC | 20041013 | $853K | Direct Mail, Canvass Brochure |
| Haddow Communications | MD | 20020930 | $703K | Media Fees |
| FieldWorks | DC | 20041013 | $591K | Fees & Concessions |
| FieldWorks | DC | 20040930 | $528K | Printing |
| Winning Connections | DC | 20041013 | $459K | Telephone |
| Mack-Sumner Communications, LLC | VA | 20141023 | $412K | Direct Mailers |
| FieldWorks | DC | 20040831 | $407K | Fees & Concessions |
| Virginia Chapter Sierra Club PAC | VA | 20130821 | $400K | Direct Contribution |
| Mack-Sumner Communications, LLC | VA | 20140930 | $397K | Direct Mail GOTV |
| Waterfront Strategies | DC | 20141024 | $366K | Radio Buy |
| Mack-Sumner Communications, LLC | VA | 20141007 | $323K | Direct Mailers |
| The New Media Firm, Inc. | DC | 20141015 | $291K | GOTV Media Placement |
| GRS Consulting, LLC | MN | 20080325 | $263K | Fees & Concessions |
| Winning Connections, Inc. | DC | 20020930 | $260K | Fees & Concessions |
| Sierra Club Nevada PAC | NV | 20181018 | $250K | Contribution |
| Sierra Club PAC Michigan Chapter | MI | 20060814 | $225K | Contribution |
| The New Media Firm, Inc. | DC | 20141001 | $199K | GOTV Media Placement |
| Crounse, Malchow, Schlackman & Hoppey | DC | 20020930 | $180K | Fees & Concessions, Media Fees |
| Winning Connections | DC | 20040930 | $162K | Fees & Concessions |
| America Votes | DC | 20060726 | $150K | Membership dues |
| Haddow Communications | MD | 20041231 | $149K | Media Fees |
| Mack-Sumner Communications, LLC | VA | 20141020 | $149K | Direct Mailers |
| FieldWorks | DC | 20040731 | $145K | Fees & Concessions |
| Malchow, Schlackman, Hoppey & Cooper Inc. | DC | 20040930 | $142K | Fees & Concessions |
| Crounse, Malchow, Schlackman & Hoppey | DC | 20021016 | $121K | Fees & Concessions, Printing |
| Grassroots Enterprise | CA | 20041013 | $120K | Fees & Concessions |
| Nevada State Democratic Party | NV | 20200929 | $115K | Direct Contribution |
| MBNA | DE | 20041231 | $111K | Fees & Concessions, Printing & Meetings |
| Virginia Chapter Sierra Club PAC | VA | 20130730 | $100K | Direct Contribution |
| America Votes | DC | 20071231 | $100K | Annual Dues |
| America Coming Together | DC | 20041031 | $100K | Contribution |
| Virginia Chapter Sierra Club PAC | VA | 20171012 | $100K | Direct Contribution |
| Great American Media, Inc. | PA | 20080430 | $94K | Fees & Concessions |
| Lake, Snell, Perry & Associates Inc., | DC | 20040930 | $92K | Consultant Fees, Fees & Concessions |
| Crounse, Malchow, Schlackman & Hoppey | DC | 20030731 | $89K | Printing and copying |
| Sierra Club Nevada PAC | NV | 20180530 | $87K | Contribution |
| Virginia Sierra Club PAC | VA | 20091007 | $80K | political program expenses |
| Sierra Club Nevada PAC | CA | 20161017 | $80K | Direct Contribution |
| Malchow, Schlackman, Hoppey & Cooper Inc. | DC | 20041231 | $78K | Fees & Concessions |
| America Votes, Inc. | DC | 20070420 | $75K | Annual Dues |
| Lake, Snell, Perry & Associates | DC | 20041013 | $67K | Polling, Focus Groups |
| Winning Connections | DC | 20041031 | $67K | Fees & Consessions |
| Winning Connections | DC | 20060809 | $61K | Fees & Concessions |
| Haddow Communications | MD | 20041031 | $57K | Media fees |
| Malchow, Schlackman, Hoppey & Cooper | DC | 20040731 | $52K | Fees & Concessions |
| SWAY LLC | MD | 20160210 | $50K | Media Ad Buy for South Carolina and Nevada |
| AFL-CIO | DC | 20080801 | $50K | Polling Consortium Cost Share |
| Democratic Governors Association | DC | 20200110 | $50K | Direct Contribution |
| Democratic Governors Association | DC | 20240205 | $50K | Direct Contribution |
| America Votes | DC | 20090723 | $50K | Dues |
| America Votes | DC | 20031231 | $50K | Contribution |
| Colorado for All | CO | 20181220 | $50K | Contribution |
| Haddow Communications | MD | 20041013 | $49K | Media Fees |
| Winning Connections | DC | 20041231 | $46K | Fees & Concessions |
| BattleAxe Digital | VA | 20260723 | $46K | Advertising |
| Great America Media, Inc. | DC | 20051031 | $42K | Fees & Concession, Fees - Media |
| America Votes | DC | 20061220 | $42K | Contribution |
| MBNA | DE | 20041031 | $42K | Fees and concessions, printing, travel, meetings |
| Virginia Sierra Club PAC | VA | 20091018 | $40K | political program expenses |
| Dewey Hub | NY | 20041013 | $40K | Telephone |
| Virginia Chapter Sierra Club PAC | VA | 20170919 | $37K | Direct Contribution |
| Feit Electric Company | CA | 20080430 | $36K | Supplies expense |
| Burnside and Associates | CA | 20041013 | $35K | Mail and Auto Dial to new registrations |
| Lichtman, Trister & Ross | DC | 20041231 | $35K | Legal Fees |
| Winning Connections, Inc. | DC | 20021016 | $34K | Fees & Concessions |
| Facebook | CA | 20181106 | $34K | Facebook Ad Buy (amended to reflect actual cost) |
| Sierra Club VA Political Action Committee | VA | 20071031 | $32K | Contribution |
| Varadero Communications | DC | 20080430 | $32K | Fees & Concessions |
| Malchow, Schlackman, Hoppey & Cooper, Inc. | DC | 20061231 | $31K | Mailer design and production |
| Chromista | CA | 20181017 | $31K | Film Production Costs (amended to reflect actual cost) |
| Malchow, Schlackman, Hoppey & Cooper, Inc. | DC | 20060810 | $30K | Fees & Concessions |
| Chromista | CA | 20181017 | $30K | Film Production Costs |
| Twitter | CA | 20181106 | $29K | Twitter Ad Buy |
| Balcony Films | CA | 20041013 | $29K | Production & Distribution Consultation |
| Sierra Club VA Political Action Committee | VA | 20071019 | $28K | Contribution |
| US Treasury | DC | 20061130 | $28K | Taxes, permits, and license |
| Malchow, Schlackman, Hoppey & Cooper Inc. | DC | 20051031 | $28K | Fees & Concessions |
| Tracey Buckman | DC | 20031231 | $28K | Consulting fees |
| Facebook | CA | 20181016 | $26K | Facebook Ad Buy |
| Public Interest Projects | NY | 20021016 | $26K | Fees & Concessions |
| Lake, Snell, Perry & Associates Inc., | DC | 20040831 | $26K | Consultants |
| SWAY LLC | MD | 20160210 | $25K | Production cost for ad ran in South Carolina Nevada |
| America Votes | DC | 20100308 | $25K | Dues |
| Sierra Club PAC Washington State | WA | 20170911 | $25K | Direct Contribution |
| Democratic Governors Association | DC | 20201016 | $25K | Direct Contribution |
| Democratic Governors Association | DC | 20210907 | $25K | Direct Contribution |
| Blaemire Communications | VA | 20041013 | $25K | Fees & Concessions |
| Democratic Legislative Campaign Committee | DC | 20180105 | $25K | Direct contribution to support electoral and legislative work in the state of Nevada only. |
| Democratic Governors Association | DC | 20230310 | $25K | Direct Contribution |
| Clean Water Fund | MI | 20061027 | $25K | Fees and Consessions |
| DDB Bass & Howes | WA | 20041013 | $25K | Consultant Fees |