As a matter of fact, it seems that Belichick was still contacting the former Patriots backup quarterback 49ers last October. According to Sports Illustrated, Belichick sent a congratulatory text to Garoppolo after each one of his starts with the 49ers last season, which means the Patriots coach sent at least five texts to Garoppolo.to the
Although it's certainly possible that Belichick has sent congratulatory texts to multiple former players, Garoppolo and his family seemed to paint a picture this week that Jimmy was actually pretty tight with his former coach. During an interview with Sports Illustrated, Garoppolo's mom Denise said that Belichick "really liked" her son, and that's why he might have traded Jimmy to the 49ers, instead of taking a bigger offer from the Browns.
"Bill really, really liked Jimmy," Denise said. "Not like they were warm and fuzzy -- but they both knew it was there."
In a separate interview with Bleacher Report, Jimmy Garoppolo said that a big reason he was able to relate to Belichick was due to the .
"There was no BS-ing around," Garoppolo said. "I related to him in that way, as crazy as it sounds. He's different than he is with the media. He has dry humor -- he would say some stuff that was borderline mean."
Although there aren't too many people who have insight into Belichick's thought process, 49ers coach Kyle Shanahan did get to talk to the Patriots coach before the Garoppolo trade went down, and Shanahan is convinced that Belichick didn't want to trade his backup quarterback.
"I know New England wanted to keep him there and keep him on ice before Tom eventually retired," Shanahan said. "But what was exciting for me was that New England knew he wasn't going to re-sign there. [Garoppolo] wanted to start and he wanted to play. He forced their hand."
The trade of Garoppolo was definitely the most shocking move of the 2017 NFL season. The trade was shocking for multiple reasons: For one, the Patriots could've gotten more in return (the Browns for Garoppolo's services). Another thing that made the move shocking is the fact that the Patriots basically spent their entire 2017 offseason insisting that they weren't going to trade Garoppolo, only to turn around and trade him one day before the deadline.
Belichick has never explained to anyone why he made the trade, including his own team, and as noted by Sports Illustrated, "even longtime players and staff members have no idea what went into the decision."
According to an ESPN report from January, Belichick was basically forced to trade Garoppolo by team owner Robert Kraft. In that report, ESPN notes that Belichick "was furious and demoralized" after being forced to trade his backup. If Belichick truly viewed Garoppolo as his quarterback of the future while also having a tight relationship with him, it's easy to see why the Patriots coach would've been upset if he was forced to trade him.