This ain't football. It's also his brother and Dennis Wyrick who are handling Shane. Not Drew.
Shane has no leverage. Unlike NFL players, holdouts don't work as a form of leverage to get your contract demands met in baseball.
Rosenhaus Sports is also trying to make in-roads in the world of baseball, as they only entered baseball agency 4 years ago. They only represent 2 players currently. They aren't going to take the same approach the football side of things takes, they are trying to build a brand in the baseball world. And yes, I understand as a sports agency you grow your business by taking care of your clients, the players, but you also can't burn bridges with front offices in your infancy.
It all depends on if Shane/RSR are hellbent on making it to free agency, which wouldn't match their actual actions with regards to their relationship with Cleveland or any message sent from either party.
Lindor and Bauer made it clear years before they were set to be free agents that they were going to hit the open market and wouldn't even entertain an extension. Obviously Lindor never did, but he also got paid everything him and his group wanted and then some by making the Mets bend over and take it.
That hasn't happened with Shane.
It's not wishful thinking. It's reality. There is absolutely a chance they can get something done.