When Is The Last Time The Light Side Of The Force Made A Big Time Free Agency Signing?
Don't get me wrong--the front office for the Light Side can identify talent better than anybody. When it comes to the draft, they've hit on so many big time players. Obi-Wan had a great career. Luke Skywalker had a great career. Rey's career is young but seems promising. Yoda is obviously the greatest to ever do it. Anakin Skywalker had a chance to be even better but that's where the Dark Side comes in. Because as great as the Light Side is at drafting, the Dark Side is almost even better when it comes to free agency.
Think about it. The front office for the Dark Side is so much better at looking at their roster, assessing their team needs and acquiring assets. They were able to sign Count Dooku in free agency from the Jedi Order. They made the biggest splash in free agency history when they signed Anakin Skywalker to a long-term deal during the peak of his career. And most recently they were able to sign Ben Solo in free agency, which hasn't been working out as well as they'd like up to this point but who knows what type of season Kylo Ren is about to have in Rise of Skywalker. The fact of the matter is that the Dark Side is constantly going out there and signing the biggest names on the free agency market, meanwhile the Light Side hasn't been able to do shit besides draft.
Now I know what some of you might be thinking to yourselves right now. "But what about when Darth Vader ends up saving Luke and killing Palpatine?". But that wasn't as much of a free agency signing as it was a deal at the trade deadline. The Light Side picked up Vader at the deadline on an expiring contract and then that was the end of it. Great trade, for sure, but that is like the same thing when a player decides to sign a 1-day contract with his original team just because he wants to retire with that organization. Vader wanted to retire on the Light Side.
I'd say the one thing that is really holding back the Dark Side is their coaching. Palpatine killed Plagueis. Vader killed Palpatine (or at least we thought). Kylo Ren killed Snoke. All these dudes are out here killing their coaches. But as far as the front office goes? The Dark Side should win GM of the Year every single season.