The front office rejects all of my pleas to trade the players on the roster; it's not easy to get what you want like it was in 2k13. Also, is there ever a moment where the GM asks you what player you want on the team?
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There are two times where the GM will ask you who you want on the team.
1. If you lose a lot of games, you will get a "tired of losing option" when sitting down with the GM where you can pick 5 players on other teams and the CPU will choose who will get traded for one of the players you have selected.
2. Right before the trade deadline. Works just like tired of losing option without the need of losing games.
To have a player traded on your team, you need to play well and show that you have all-star potential. Usually after cracking the starting lineup and having a few good games, the option to have a player traded will come up. Sit down with your GM and they will ask you who you want on your team to be traded away (you may only select one player of course).