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Test Your DeStefano Generation IQ

by Paul Bass | Dec 20, 2013 2:30 pm

(4) Comments | Commenting has been closed | E-mail the Author

Posted to: City Hall

Paul Bass Photo A generation of city officials who helped run New Haven for the past two decades reunited in City Hall. How many can you recognize?

The occasion for the reunion Thursday afternoon: the unveiling of a portrait of Mayor John DeStefano, who retires at the end of the month after 20 years in office, the longest tenure of any chief executive in New Haven history.

DeStefano invited the people who helped him rebuild and reimagine the city over those two decades to gather one last time in City Hall. The atrium was filled with warm embraces and nostalgic memories. “You all have given me so very, very much. I thank you,” DeStefano (pictured) told them, choking up. “I feel like the richest and happiest guy in New Haven.” (Click here to read his full remarks, including a reference to the need for City Hall to “attack scumbag landlords.”) Photos of some of the reuniting officials, past and present, follow. See if you can guess their names. Helpful hints are included under their pictures; the answers appear at the bottom of the story.

1. These two men never tried to win popularity contests—whether deciding on your tax bill, or your parking fine.

2. Her portfolio featured the city’s neediest cases.

3. He moved from a bank to City Hall to make sure the money came in.

4. She charted policy from the mayor’s suite before moving to the “Promise” scholarship program and then the state Board of Ed; he went from transportation duties to economic development.

5. She answered reporters’ calls at all hours, even when in labor; he has run the staff for an independent branch of government.

6. He took the politics out of a top City Hall job after a corruption scandal.

7. She ran the shop on the second floor before taking on public housing.

8. One kept tabs on the mayor at home, the other at the office.

9. She negotiated with Big Money; he negotiated with small-business owners and angry parkers.

10. He was the first African American to hold a position that, more than most, affects the daily lives of many African Americans in New Haven.

11. She lives every day the issues she champions.

12. Their job: Tell officials what’s legal.

13. He ran the schools and was perhaps the most trusted political ally of the mayor; she was one of 11 (count ‘em) mayoral spokespeople in addition to serving as spokeswoman for the man beside her in the photo.

14. He spoke for the mayor before becoming a politician himself.

15. His job brought him into contact with factory owners, bankers, factory workers, and people who dreamed of opening their own businesses.

16. She, too, handled the “neediest” portfolio before becoming a deputy at the housing authority.

17. Two of them flew from Austin, Texas, for Thursday’s reunion; the woman on the right has spend decades in local politics, from the mayor’s suite to the state legislature to the Board of Aldermen.

18. In his first years in City Hall, DeStefano tapped this man just out of Yale to craft education policy. He returned to the state last year to run the state’s education policy, and control some of the purse strings for schools money coming to New Haven.


1. Assessor Bill O’Brien (1999-2003; 2008-2011) & traffic and parking czar Brian McGrath (1194-2003).

2. Community Services Administrator Chisara Asoumugha (2010-2012).

3. Tax Collector C.J. Cuticello (1998-2008).

4. Legislative aide Emily Byrne; & traffic and parking czar (2007-2010) and then development deputy (current) Mike Piscitelli.

5. Mayoral spokeswoman Jessica Mayorga (2007 to 2011) and Office of Legislative Services chief Al Lucas (1988-present).

6. Chief of Staff Jim Horan (1998-2000).

7 Chief of Staff (2004-6) and housing authority chief (current) Karen DuBois-Walton.

8. First Lady Kathy DeStefano and Executive Administrative Assistant Rosemarie Lemley.

9. Development Administrator Kelly Murphy (2005-present) & traffic & parking czar (2003-6) and development staffer Paul Wessel.

10. Police Chief Melvin Wearing (1997-2003).

11. Disability services chief Michelle Duprey (1999-present).

12. Corporation Counsels Steven Mednick (1994-6) and Thomas Ude (2001-7).

13. Schools Superintendent Reggie Mayo (1992-2013) and mayoral spokeswoman Catherine Sullivan-DeCarlo (1994-1998).

14. Mayoral spokesman Roland Lemar (2003-4), now a state representative.

15. Business Development Director Sal Brancati (1994-2000).

16. Community Services Administrator Sheila Allen Bell (2001-6).

17. Shonu Gandhi, a DeStefano gubernatorial campaign manager; and former Chiefs of Staff Julio Gonzalez (2001-4) & Andrea Jackson-Brooks (1994-8).

18. Former mayoral policy aide, current state schools chief, Stefan Pryor.

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posted by: anonymous on December 19, 2013  7:53pm

Great quiz.

posted by: Bill Saunders on December 19, 2013  8:05pm

Let’s see the Portrait!!

posted by: Claudia Herrera on December 20, 2013  1:42am

What happen to Sean Matteson?

posted by: Threefifths on December 20, 2013  11:12am

Test Your DeStefano Generation IQ.

All puppets.

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