It’s worth asking, even if the answer seems obvious: at what point will Manny Ramirez realize he finally stepped over the line? Undoubtedly there is considerable sentiment that Ramirez, like most other pampered and spoiled professional athletes, doesn’t even possess the gene necessary to express regret. And that may be true. But you have to think at some point on his trip across country to hook up with Casey Blake and the rest of the L.A. Dodgers that it had to flash at least momentarily in his mind that he may have pushed his clown act a tad too far.

Teams, particularly contending teams and particularly the defending World Series champs, don’t trade a current superstar and lock Hall of Famer in the middle of a pennant race without an awfully good reason. Yet it certainly seemed like the Boston Red Sox had good reason and more to send Ramirez as far away as geographically possible. Now he’s left with the realization, whether he owns up to it or not, that he carries a tarnished image to a city where image is everything.

Ramirez will always be seen as a somewhat beloved overgrown kid to Cleveland Indians fans. Like C.C. Sabathia, Ramirez grew up with the Indians. At every step of his development from the low minors to his pro debut to his last at bat with the Indians, Ramirez possessed one of the sweeter swings ever. He still does. As a neophyte major leaguer, his mostly harmless goofiness gave him the appeal of a golden retriever. The stories about a young Ramirez traipsing around like someone’s kid brother, absentmindedly leaving five-figure uncashed checks lying around in his car, bumming rides off of the clubhouse attendants, grabbing just about any bat in the rack at any moment, only made him endearing.

When Ramirez left Cleveland, he wasn’t excoriated by the fans the way Jim Thome was, even though he made the same unabashed money grab. Sure, there has been the occasional derogatory reference to him as Manny Dinero, but his returns to Cleveland have generated mostly a “wish he was still here” reaction whereas with Thome fans still boo him and consider him to be a traitor.

All of that may be due to the fact that Thome was far more forthcoming and articulate with the media, which ended up costing him dearly with the public. His claims of wanting to remain in Cleveland ultimately rang hollow. Ramirez in contrast never said much of anything to anyone. At the time, he simply let his agent, Jeff Moorad, manipulate the local media as he angled for the best deal for his client. It probably wasn’t a calculated move on Ramirez’s part so much as it was just another example of his seemingly casual indifference toward his career which to most seemed to consist of the beautiful simplicity of “see ball, hit ball, occasionally cash a check.”