| Date | Grid | Clue | Author | Editor |
| Wed, Aug 14, 2019 | 1D | Wall St. pro | David J. Kahn | Shortz |
| Sun, Mar 31, 2019 | 38D | Wall St. professional | Andrew J. Ries | Shortz |
| Sun, Apr 22, 2018 | 91D | Wall St. worker | Ross Trudeau | Shortz |
| Wed, Oct 11, 2017 | 26D | Wall St. trader | David J. Kahn | Shortz |
| Sun, Jan 01, 2017 | 101A | Hedge fund pro | Matthew Sewell | Shortz |
| Sun, Apr 19, 2015 | 24D | Hedge fund pro | Don Gagliardo and Zhouqin Burnikel | Shortz |
| Thu, Aug 28, 2014 | 8A | Wall St. operator | Ned White | Shortz |
| Tue, Feb 04, 2014 | 30A | Wall St. operator | David Steinberg | Shortz |
| Tue, Jul 30, 2013 | 35D | Wall St. trader | Peter A. Collins | Shortz |
| Thu, Feb 14, 2013 | 51A | Wall St. insider, maybe | Jules P. Markey | Shortz |
| Sun, Dec 05, 2010 | 11D | Wall St. worker | Ben Pall | Shortz |
| Mon, Jul 06, 2009 | 7D | Wall St. whiz | Fred Piscop | Shortz |
| Sat, Aug 02, 2008 | 10D | Trading specialist, briefly | Karen M. Tracey | Shortz |
| Fri, May 09, 2008 | 18A | Market figure, briefly | Jim Page | Shortz |
| Tue, Nov 21, 2006 | 49A | One working on the margin, briefly? | Stella Daily and Bruce Venzke | Shortz |
| Sun, Apr 23, 2006 | 10D | Hedge fund whiz, for short | Joe DiPietro | Shortz |
| Sat, Jul 23, 2005 | 61D | Wall St. type | Joe DiPietro | Shortz |
| Wed, Jan 12, 2005 | 7D | Wall St. worker | Alan Arbesfeld | Shortz |
| Sun, Apr 06, 2003 | 12D | Financial speculator, for short | Joe DiPietro | Shortz |
| Sun, Apr 14, 2002 | 33D | Wall St. type | David J. Kahn | Shortz |
| Sun, Aug 05, 2001 | 102A | Wall St. worker | Peter Gordon | Shortz |
| Sat, Apr 28, 2001 | 52A | Wall St. figure | Rich Norris | Shortz |
| Thu, Nov 30, 2000 | 7D | Wall St. maven | Manny Nosowsky | Shortz |
| Wed, May 03, 2000 | 30D | Wall Street wheeler-dealer, briefly | Nancy Salomon | Shortz |
| Tue, Mar 28, 2000 | 59D | Wall St. whiz | Fred Piscop | Shortz |
| Sat, Jan 29, 2000 | 34D | Short trader? | Rich Norris | Shortz |
| Thu, Dec 23, 1999 | 26D | Certain Wall Streeter, briefly | Joe DiPietro | Shortz |
| Wed, Oct 06, 1999 | 40D | Wall St. figure | Fred Piscop | Shortz |
| Sun, Apr 18, 1999 | 12D | Sophisticated trader, for short | Frank Longo | Shortz |
| Sat, Oct 24, 1998 | 19A | Short trader? | Rich Norris | Shortz |
| Sun, Jun 21, 1998 | 93A | Wall Street whiz | Jim Page | Shortz |
| Tue, Jun 18, 1996 | 34A | Mediator: Abbr. | E. C. Gorski | Shortz |
| Mon, Jun 17, 1996 | 47A | Wall Street operator, for short | S. L. Robbins | Shortz |
| Sun, Dec 10, 1995 | 2D | Wall St. dealer | Jim Page | Shortz |
| Sun, Feb 19, 1995 | 34A | Wall Street worker, for short | Alfio Micci | Shortz |
| Sat, Apr 16, 1994 | 50D | Wall Street wheeler-dealer | Rand H. Burns | Shortz |
| Thu, Mar 17, 1994 | 35D | Wall Street operator, for short | Jim Page | Shortz |