20He’s Always Hated Tony Stark
However, while Winter Soldier wasn’t thinking straight (he was brainwashed at the time) when he eliminated the Starks, he’s certainly no fan of Tony’s.
Tony Stark and Winter Soldier always seem to find themselves on opposite sides. They face off in Captain America: Civil War when they fall on opposite sides of the inter-Avengers conflict, and they come to blows in the comic book universe as well.
Tony Stark certainly has a very valid reason
for hating Winter Soldier. After all, it was the brainwashed fighter that made him an orphan all those years ago.
In the comic book canon, Bucky Barnes takes up the mantel of Captain America after Steve Rodgers’ supposed passing, but he blames Stark for Rodgers’ demise in the first place because Rodgers was in S.H.E.I.L.D custody when the Red Skull orchestrates his assassination.