More details and sauce on plane deaths. Haven't found as much during Obama era…
Clintons
• 19 Feb 1986
o Barry Seal: Drug running TWA pilot out of Mena AK
o https://en.wikipedia.org/wiki/Barry_Seal
• July 1992,
o C. Victor Raiser, II: major player in Clinton fundraising
o private plane crash
o http://www.nytimes.com/1992/08/02/obituaries/victor-raiser-52-financial-aide-in-clinton-presidential-campaign.html
• 23 Feb 1993
o Major General William Robertson
o Col. William Densberger
o Col. Robert Kelly
o Spec. Gary Rhodes
o Crash of presidential helicopter
o (no news articles could be found)
• 20 May 1993
o Major William S. Barkley, Jr.
o Captain Scott J. Reynolds
o Sergeant Brian Hanley
o Sergeant Tim Sabel
o Crash of presidential helicopter
o http://www.nytimes.com/1993/05/20/us/4-marines-die-in-crash-of-presidential-copter.html
• 10 Sep 1993
o Dr. Stanley Heard: Chairman of National Chiropractic Health Care Advisory Committee, served on Clinton's advisory council and treated his mother, stepfather, and brother
o (small plane crash), small plane crash
o https://www.washingtonpost.com/archive/local/1993/09/11/four-die-in-2-plane-crashes/77a3e9ca-70a9-427e-98a5-3c53ecc35682/
• 01 Mar 1994
o Herschel Friday: Attorney and Clinton fundraiser, private plane exploded
o https://en.wikipedia.org/wiki/Herschel_Friday
• 3 Apr 1996
o Ron Brown, Secretary of Commerce and former DNC chairman, along with 34 other people, including Charles Meissner, Asst. Secretary of Commerce who gave John Huang
o special security clearance, crash of USAF CT-43 (modified Boeing 737)
o https://en.wikipedia.org/wiki/Ron_Brown_(U.S._politician)
• 16 July 1999
o John F Kennedy Jr.: competitor to Hillary for NY seat in the US Senate
o crash of private plane
o https://en.wikipedia.org/wiki/John_F._Kennedy_Jr.#Death
Obama
• 12 Feb 2009
o Beverly Eckert: activist and advocate for 9/11 Commission
o Crash of Colgan Air Flight 3407, just days after meeting with Obama
o https://en.wikipedia.org/wiki/Beverly_Eckert
• 11 Dec 2013
o Loretta Fuddy: approved Obama’s birth certificate
o private plane crash
o https://en.wikipedia.org/wiki/Loretta_Fuddy
• 08 March 2014
o Philip Wood, an IBM employee from TX
o The other Americans aboard were children: Nicole Meng, 4, and Yan Zhang, 2.
o MH370
o https://en.wikipedia.org/wiki/Malaysia_Airlines_Flight_370
• 17 July 2014
o A 19-year old U.S. citizen from Indiana
o MH17: shot down over Ukraine by Russian sympathizers (unrest fomented by inept Obama foreign policy), 283 passengers and 15 crew, 1 U.S. citizen
o https://en.wikipedia.org/wiki/Malaysia_Airlines_Flight_17
• 02 oct 2015
o Capt. Jonathan J. Golden, 33, of Camarillo, California;
o Capt. Jordan B. Pierson, 28, of Abilene, Texas;
o Staff Sgt. Ryan D. Hammond, 26, of Moundsville, West Virginia;
o Senior Airman Quinn L. Johnson-Harris, 21, of Milwaukee;
o Senior Airman Nathan C. Sartain, 29, of Pensacola, Florida;
o Airman 1st Class Kcey E. Ruiz, 21, of McDonough, Georgia
o Killed aboard a military C-130 trasport that crashed in Afghanistan.
o http://www.cnn.com/2016/04/19/politics/us-air-force-plane-crash-afghanistan/index.html