As the MLB trade deadline looms, the Cleveland Guardians are facing a difficult but familiar dilemma: hold on to beloved stars and hope for a postseason run, or make the painful decision to pivot toward the future.

The most pressing name in the conversation is former Cy Young winner Shane Bieber, whose return to the mound could double as his final appearance in a Cleveland uniform.

“If there’s an ounce of juice in that puppy at Canal Park,” Jack O'Rourke said bluntly, “Shane Bieber is not going to be on the roster in a couple of days.”

It’s not just about performance — Bieber has been incredible when healthy — but about philosophy. In a small-market system like Cleveland's, the margin for error is razor-thin, especially with injury-prone veterans.

“The production’s there. He’s been so consistent whenever he’s out there,” O'Rourke acknowledged. “But with an organization like ours where you don’t spend money, it’s really tough to… justify going out there and giving that next contract to guys who are injury-prone.”

The comparison to Michael Brantley’s exit was not made lightly. “It reminds me of Michael Brantley a lot in a way… I think it’s going to be sadly a situation like Brantley where he’s just going to walk at the end if they don’t move on from him this week.”

Still, Bieber’s value on the market isn’t what it once was. “What are you going to get for Bieber though? That’s the thing,” Jack said. “He does have the opt-out clause at the end of the year… so I don’t even know how much you’re going to get for Shane Bieber at this point.”

That uncertainty could extend to more than just Bieber. The Guardians are rumored to be receiving significant trade interest in outfielder Steven Kwan, and there's a growing sentiment that Cleveland may explore a broader reset.

“I think it’s time to say goodbye, to be honest. And not in a way of giving up on this season,” Jack noted. “I think that last wild card spot is going to be within reach… but again, I’m at the point where it’s like José Ramírez is 32 years old, about to be 33. I’m thinking of how can we optimize him best.”

The logic is cold but calculated. “There’s nothing you could do in the next week… that’s going to win the World Series this year,” Jack said. “So, I think if that’s the case, you got to do whatever you can to start moving towards next year.”

That means hard decisions — and likely emotional ones. “I don’t think they’re going to hand Steven Kwan the golden contract in the offseason,” O'Rourke added. “So, I think the best thing you can do probably is move on from him.”

According to Ken Rosenthal, “Steven Kwan is generating ‘a ton of trade interest.’” Teams like the Dodgers, Blue Jays, Phillies, and Padres are reportedly in the mix. 

Some even suggested the team consider dealing reliever Cade Smith. “If I’m looking at purely like trying to get better while José Ramírez is still here… factoring in that Kwan and Bieber are probably not going to be around much longer… I think you have to mini sell.”

Beyond the roster decisions, there was even some commentary on long-time pitching coach Carl Willis, whose persistence — and patience — has become both a badge of honor and a running joke.

“Carl Willis every single year runs his ass back out there thinking, you know what, maybe if I speak enough sweet nothings… they’re going to look so good that the batters are like, hey, maybe this year we have to start hitting the ball,” one panelist joked. “Carl, it’s not going to happen. Move on. Go into retirement. Go hang out with Tito or something.”

For a team that’s hovered near contention despite injuries and inconsistency, the temptation to stand pat is understandable. But the growing chorus suggests Cleveland should act now — not to tank the season, but to thread the needle between competing today and preparing for tomorrow.

“It sucks to say—the best thing to do is move on and get whatever you can,” Jack said. “Because this team’s not going to win the World Series this year.”