Having played under Skiles with both the Magic and previously the Milwaukee Bucks, Jennings was perplexed as to why his coach would quit after just one year on the job.
Shortly thereafter, however, Jennings figured it out, although he didn't share his findings.
All signs point to a disconnect between Skiles and general manager Rob Hennigan. Skiles carries a well-earned reputation for being a veteran's coach, while Hennigan put together a young roster, so there were bound to be differences.
For example, the two apparently disagreed on the deployment of Elfrid Payton, according to Josh Robbins of the Orlando Sentinel. Jennings was eventually brought in at the trade deadline to add some stability at backup point guard.
Other issues also cropped up. ESPN's Brian Windhorst reports that Skiles was upset that an option year in his contract wasn't picked up. He led the Magic to a 10-win improvement, but most of that came early on when they were 19-13 to start. They eventually finished with just 35 wins in 2015-16.
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