David Ross is in a weird position as manager of the Chicago Cubs. He catches a lot of flack from fans about his managerial decisions, but he's quite literally managing a team that is built to fail. In most professions, it is hard to do a good job when you aren't given the tools to succeed. It's kind of like being told to become fluent in French and being given 26 guys who have been to France once as your language teachers.
As such, when the trade deadline came and Jed Hoyer essentially traded away Ross's entire bullpen, it's fair that the Cubs' skipper felt some joy when Willson Contreras and Ian Happ remained on the North Side. He said as much.
I Mean... Yeah
Outside of the "duh" thought going through your head right now, keep in mind that Ross is here to do the job expected of him by management. This season, the Cubs aren't supposed to be competitive. Ross is supposed to keep the clubhouse steady and get looks for his younger players. Contreras and Happ are All-Stars, but management made it pretty clear they were interested in moving on from them. Ross's job would have been to maximize opportunities for other players, and you have to imagine he was preparing for that.
Still, you're talking about a former professional athlete and a two-time World Series champion. It's incredibly hard to be a competitive person and be content losing. If the Cubs traded Contreras and Happ, it may have fit with Hoyer's vision better. However, Ross clearly still wants to try to win as a manager. He still wants his players to experience winning. Simply put, Willson Contreras and Ian Happ sticking around gives the Cubs a much higher chance of winning.
Yes, the Chicago Cubs would love to get a better chance at the first overall pick. However, David Ross is cool with trying to win more games right now. It's better for his track record as a manager. Having two All-Stars in your lineup every day has to give Ross a jolt of energy he was preparing to, well, not have.