Is it fair to say that it’s never too early to start thinking about offseason transactions? Well, when you’re talking about one of the best left-handed starting pitchers to reach the free agent market in the last 10 years, I’d say that, yes, it’s fair.

Cole Hamels is the guy I’m talking about, and, unless the Phillies manage to work out an extension (something they are still working on), he’ll be available for teams to bid on come November. He sports a career 3.38 ERA, 126 ERA+, 1.138 WHIP, and 3.17 FIP over 1187.2 innings. He’s been quite good, and, at 28, there’s still a lot of life left in that arm. Wouldn’t he look pretty nice as an offseason free agent target? Wouldn’t he look even better taking the ball for the Cubs in early April 2013?

Though he’s not ready concede that he’ll test free agency, and the Cubs are unwilling to confirm future plans, Hamels does admit that the possibility of pitching in Chicago intrigues him. From the Sun-Times:

“[If the Phillies] don’t view me or see me in their plans, then obviously I have to go outside to look, and the Cubs would be a team I would be more than happy to [consider],” he told the Sun-Times, “just because of the fact the city hasn’t won, they’re a baseball town, like Philly, and I think seeing Theo there, obviously trying to build a team, that shows they do want to win, which obviously excites anyone.”

The key is that likelihood of winning, which Hamels, the 2008 World Series MVP, said is a priority for him, whether he stays in Philadelphia or becomes a free agent.

“I think they’re starting to get some good young talent, and that’s kind of what we did, and how we won,” he said of a Phillies team that has been to the playoffs for five consecutive years, including the 2008 championship and 2009 NL pennant. “We built around home-grown talent and then got a few good pieces to [add to] it. That’s where you have to start. And if that’s what the Cubs are doing, then they have a good vision.

“And anybody that ever has the opportunity to play for that city and win in that city, they’ll take that memory forever, and a lot of people would be really jealous that they weren’t part of that team.’’

It’s certainly nice that the Cubs have an additional selling point – be a part of history.

Given the Cubs’ organization’s current makeup, however, does signing Hamels make sense? Are they going to be in a position to “go for it” in 2013? Do they have to be ready to “go for it” by 2013 in order to consider signing Hamels?

And, another corollary: does the team’s plan for Matt Garza impact the decision?

It would be easy to say that the Matt Garza story will dovetail with the Cubs’ anticipated pursuit of Hamels. After all, both will be 29 next year, and why would you sign one after trading the other?

I’m not so sure it’s that simple. You can only trade a guy when you have him, and you can only sign a guy when he’s available. The Cubs could believe they can improve the team overall by trading Garza, regardless of what happens to the rest of the team. It’s conceivable that the Cubs could pick up two ML-ready starting pitchers with high upside (plus other prospects) who could help the team in 2013, and, combining that with the $10 million saved, which could go to another free agent, there might be a net improvement on the field in 2013. If that’s true, signing Hamels is a decision to be made completely independently of the Garza decision.

It is superficially attractive to have both pitchers in the rotation going forward, but it might not be best for the organization as a whole, particularly when considering that the offensive core of the team is going to be some six years younger than Garza/Hamels (Starlin Castro and Anthony Rizzo are 22, Brett Jackson is 23, for examples). It might be financially best to have only one of those two starting pitchers signed long-term as a “veteran ace.” If that’s true, then you’ve got a choice: you can have Garza on a long-term deal, or you can have Hamels on a long-term (more expensive) deal PLUS the prospects netted by trading Garza.

I’m not necessarily advocating trading Garza, mind you. I’m simply saying I don’t see a connection between the decision to trade or not trade Garza, and signing Hamels. There are scenarios where trading Garza this Summer and then signing Hamels in the Winter make sense. Indeed, in some of those scenarios, the Cubs come out better than if they’d tried to lock them both up long-term. But, don’t misunderstand me: it would be pretty sweet to have both.

As for Hamels, specifically, I’m very, very hopeful that the Cubs go all out on trying to sign him. With teams increasingly trying to lock up their own players with long-term extensions, there may be fewer and fewer opportunities to acquire ace-caliber pitchers for only money. And, even if the Cubs aren’t ready to compete in 2013, you’ve got to sign these guys when they’re available. Getting Hamels in December is as much about 2014 and beyond as it is about 2013.

Make no mistake, though: the contract would be ugly. Hamels is going to get an absurd contract – 8 to 10 years and more than $200 million isn’t out of the question, given the latest trends. This is the way the business is moving, however, and we’re going to have to adjust to a “new normal.”

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