He made promises to critical veteran players to keep the team intact if they would take less money, but with Colon scoffing at a reported three-year, $36 million deal, the most important piece of the puzzle is missing.
They got an answer from Frank Thomas on Thursday when the veteran slugger exercised his $6 million option for next season.
Valentin believes that Williams could be gambling with other players, however, and it's a game that Valentin might not want to take part in.
"When we were talking, we weren't too far away [from a deal]," Valentin said. "I agreed to take less money, but now I don't know what's going to happen. What if I would take a little less money, but he doesn't get other players back and I'm stuck with a rebuilding team, on top of signing for less money?
"And I'm not just talking about Bartolo. We can still go far without Bartolo. We might be able to get two decent pitchers with the money they were going to give Bartolo, and our offense can score runs."
On the Sox's side of things, Valentin might not be in their plans at all if they start to see that keeping the team together will not be possible. His batting average has slipped in each of his four seasons on the South Side, going from .273 in 2000 to .258 in '01, .249 in '02 and then .237 this season. But getting 25-plus homers from the shortstop each season is something that can't be ignored, especially in the AL where power-hitting shortstops are the trend.
Valentin's struggles against left-handed pitchers are still a problem, but the leadership and fire he brings to the clubhouse can't be measured in statistics and numbers.
"It will be sad if I have to leave," Valentin said. "My last four years have been the best of my career. To have to learn a new team would be tough. I don't want to start all over again. But it's not about helping the team right now. It's about helping myself. Not money, but being able to play and win.
"I want to win, first of all. I'm sure I could go and just get money, but I want to win. I want to stay in Chicago and go back to a team that's competing. I don't want to go to a team and be a teacher or whatever. This will be my 11th season, and I want a ring on my fingers. To be a teacher, I'll wait to retire to do that.
"I'm not staying with a team that's going young. I talked to Robbie and he's in the same situation ... it has to be the right money and situation."