She once promised to Eleanor Waldorf to give Blair her Cornelius Vanderbilt engagement ring should Nate and Blair ever be engaged but when Blair witnesses Nate's troubles with his father she ends the relationship.By the second season, Nate's mother whose financial assets have been frozen since her husband's guilty departure have caught up with her and their house in Manhattan is seized, leaving Nate to lodge in temporarily with the Humphreys.Bart complimented Chuck on his speech, and said he was proud of his commitment to Blair.In season 2, with Dan's help, he and Chuck try to mend their relationship, but he suddenly dies in a limo accident.As Chuck and Blair keep digging for dirt on Bart, He gets Nate into prison and tries to kill his own son in a flight to Moscow as a deal to Chuck to keep everyone he loves safe.
He was controlling with his family, ruthless in business and demonstrated little affection for Chuck, and it's revealed that this is because he holds his son responsible for his late wife's death (Chuck's mother died while giving birth to him.) At times Bart appears to care about his son, and asked him to be his best man at the wedding.
When looking for Diana's secret, he is discovered alive.
As Life on the Upper East Side goes on with its gossip and rage of others, Chuck finds out something he was not supposed to about his father and how he pays people off to "accidentally" kill people who are after him and with information that could destroy his reputation.
He leaves to escape arrest, still addicted to cocaine and Nate punches his father before the Captain could get into his limo and fled to Dominica.
In the second season, when he returned to New York, to take Nate and his mother with him, Nate gave him a choice.