| Five-time aspirant for Presidency | 33 |
| Five-time also-ran | 18 |
| First American Railway Union president | 38 |
| Eugene who helped start the Industrial Workers of the World | 59 |
| Early U.S. labor leader | 23 |
| Early Socialist presidential candidate Eugene | 45 |
| Debutantes, slangily | 20 |
| Cotillion VIPs | 14 |
| Cotillion presentees | 20 |
| Cotillion newbies | 17 |
| Cotillion honorees | 18 |
| Coming-out party girls | 22 |
| Comers-out | 10 |
| Candidate who lost to McKinley, Roosevelt, Taft, Wilson, and Harding | 68 |
| Candidate of '08 | 20 |
| Balls' belles | 17 |
| Ball V.I.P.'s | 17 |
| Ball throwers | 13 |
| Ball honorees, informally | 25 |
| Ball girls, briefly | 19 |
| American Socialist: 1855-1926 | 29 |
| American Socialist | 18 |
| "Walls and Bars" author | 33 |
| "Unionism and Socialism" author | 41 |
| Obligation | 10 |
| Cause of red ink | 16 |
| Due | 3 |
| Score | 5 |
| Red ink | 7 |
| Borrower's burden | 21 |
| Liability | 9 |
| Something owed | 14 |
| Arrears | 7 |
| Corporate concern | 17 |
| Red-ink amount | 14 |
| Money you owe | 13 |
| It's outstanding | 20 |
| Fiscal shortfall | 16 |
| Owed amount | 11 |
| Bankruptcy cause | 16 |
| Plastic user's concern | 26 |
| Outstanding amount | 18 |
| Financial obligation | 20 |
| Credit card result | 18 |
| Subject of interest | 19 |
| Pound of flesh | 14 |
| Overcharging concern? | 21 |
| National ___ | 12 |
| Charging result | 15 |
| Chapter 11 issue | 16 |
| Cause for Chapter 11 | 20 |
| You may get into it while shopping | 34 |
| What a marker indicates | 23 |
| The red, so to speak | 20 |
| Spendthrift's hangover | 26 |
| Some are up to their ears in this | 33 |
| Net worth factor | 16 |
| Major American export | 21 |
| It might be consolidated | 24 |
| Credit card worry | 17 |
| Credit card balance, e.g. | 25 |
| Credit card balance | 19 |
| Cardholder's woe | 20 |
| Card balance | 12 |
| ___ of gratitude | 16 |
| You may get into it while making purchases | 42 |
| What red ink signifies | 22 |
| Unpaid amount | 13 |
| U.S.A. problem | 14 |
| Suze Orman topic | 16 |
| Something to stay on top of | 27 |
| Reason for imprisonment, once | 29 |
| Problem for the bottom line | 27 |
| Overcharging result | 19 |
| It's tough to be in a lot of it | 35 |
| It's not good when it's outstanding | 43 |
| It's indicated in red | 25 |
| It definitely costs to be in it | 31 |
| I.o.u., e.g. | 12 |
| Gambler's woe | 17 |
| Fiscal concern | 14 |
| Credit report item | 18 |
| Corporate problem | 17 |
| Consumer pitfall | 16 |
| Chapter 11 concern | 18 |
| Cause of bankruptcy | 19 |
| Borrowing consequence | 21 |
| Binge consequence, maybe | 24 |
| Balance sheet minus | 19 |
| 2012 campaign issue | 19 |
| You're strapped when you're in it | 41 |
| You can get it with a credit card | 33 |
| What shoppers may go into | 25 |
| What red ink symbolizes | 23 |
| What bonds represent | 20 |
| What bankruptcy discharges | 26 |
| What an IOU signifies | 21 |
| What a note signifies | 21 |
| What a borrower carries | 23 |
| Unpaid loan, e.g. | 17 |