Some experience has shown that this front office likes to hire/sign people with whom they have familiarity from previous work stops (eg. Vaughn, Ben Gordon, Willie Green). So let's look at the coaches our front office has come into contact with.
Hennigan worked for the Spurs between 2004-08.
in that span:
HC: Gregg Popovich
Assistants:
P.J. Carlesimo
Mike Budenholzer
Brett Brown
Don Newman
Chip Engelland
Chad Forcier
---(Pre-2004 Popovich Assistants)---
Hank Egan
Paul Pressey
Mike Brown
Mario Elie
---(Post-2008 Popovich Assistants)---
Jacque Vaughn (Spurs player 2006-09)
Ime Udoka (Spurs player 2010-11)
Jim Boylen
Sean Marks (Spurs player 2003-06)
Ettore Messina
Becky Hammon (Stars player 2007-14)
---(Popovich Players-Turned Head Coaches
*)---
Jacque Vaughn (Spurs player 2006-09)
Avery Johnson (Spurs player 1992-93, 1994-01)
Vinny Del Negro (Spurs player 1992-98)
Monty Williams (Spurs player 1996-98)
Scott Perry worked for the Supersonics/Thunder in 2007-08.
HC: P.J. Carlesimo
Assistants:
Scott Brooks
Mark Bryant
Ralph Lewis
Walt Rock
Brian Keefe
Paul Westhead
Hennigan later worked for the Supersonics/Thunder between 2008-12.
HC: P.J. Carlesimo, Scott Brooks
Assistants:
Scott Brooks
Mark Bryant
Ralph Lewis
Ron Adams
Maurice Cheeks
Rex Kalamian
Mark Bryant
Brian Keefe
Maz Trakh
Scott Perry worked for the Pistons between 2000-07, 2008-12
HC: Rick Carlisle, Larry Brown, Flip Saunders, Michael Curry, John Kuester, Lawrence Frank
Assistants:
Kevin O'Neill
Tony Brown
Bob Ociepka
Herb Brown
Dave Hanners
Igor Kokoskov
John Kuester
Mike Woodson
Phil Ford
Garfield Heard
Pat Sullivan
Brendan O'Connor
Sid Lowe
Don Zierden
Ron Harper
Dave Cowens
Terry Porter
Michael Curry (2007-08)
Darrell Walker
Harold Ellis
Bill Pope
Brian Hill
John Loyer
Roy Rogers
Dee Brown
Charles Klask
Matt Lloyd worked with the Chicago Bulls' Basketball operations department (following a longer period as a scout, for which I don't have good data) between 2003-07:
HC: Bill Cartwright, Pete Myers, Scott Skiles
Assistants:
Ron Adams
John Bach
Bob Thornton
Mike Wilhelm
Jim Boylan
Pete Myers
Just observing this from a distance, it seems all roads lead to P.J. Carlesimo.
So to synthesize this with
my study a few pages ago on experienced, winning coaching candidates... of the potential candidates that the Magic front office has some level of familiarity with:
Most Magic FO-familiarity: P.J. Carlesimo (Hennigan, Perry)
Best Win-Loss Record: Mike Brown (.616)
Most Playoff success: Larry Brown (NBA Championship)