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A few weeks ago, when Chicago Cubs Chairman and Owner Tom Ricketts took the bold step of extending VP of Player Personnel/International Scouting Director Oneri Fleita before a new general manager was in place, people called Ricketts naive. Foolish. Risky.

I didn’t share those sentiments, but it did get me wondering what was coming next. If Ricketts was comfortable making a decision on Fleita without the input from the next GM, perhaps he’d be comfortable doing the same with respect to Scouting Director Tim Wilken. So, when word broke a couple weeks ago that Ricketts would be meeting with Wilken this past weekend, it was fair to assume that an extension was forthcoming for Wilken, as well. After all, like Fleita, Wilken is universally respected, is considered a crucial part of the Cubs’ growing farm system, is under contract for one more year, and has already received a public endorsement from Ricketts.

Well, the two met this weekend, and sure enough, Wilken … didn’t get an extension.

Um, ok.

Don’t get me wrong, I don’t have a particularly strong reaction to Wilken not being extended. He remains under contract for 2012, and, even if I were convinced that Wilken can help this organization, I like the idea of leaving open the possibility that the next GM may want to bring in a number of “his guys,” which could include a new scouting director.

But, given the parralels of Fleita and Wilken, I remain surprised that the extension didn’t come down for Wilken. And, despite what he says, I would imagine Wilken was surprised, too.

“We knew it as far as the contract, but we talked for an hour and a half, had a real good meeting,” Wilken said of the meeting. “Just like he did in the draft, he was very supportive. He’s a good man.”

Bruce Levine’s source says Wilken was told he was a valuable part of the organization, but that Ricketts did not want to make any additional executive decisions until the new GM is in place.

But, if that’s the case, why did Ricketts extend Fleita?

The difference in the two situations, as near as I can figure, is either that Wilken is not considered as valuable to the Cubs in this transition period, or, more likely, the Cubs aren’t being pushed by another suitor in the same way that they were with Fleita. Recall, the Detroit Tigers were offering Fleita a multiple-year deal to jump ship before Ricketts locked him down. In other words, Ricketts did not want to make a decision about any of the team’s executives – be it Fleita, Wilken, or someone else – but his hand was forced with respect to Fleita. So Ricketts made a single exception.

So, what does this mean for Wilken’s future? As I said, he remains under contract, and we’ve not yet heard of any overtures from other organizations. It’s entirely possible that there’s nothing to glean from this meeting, and it only seems that there should be something because we’re viewing it through the lens of the Fleita extension. If so, the new GM will review the organization and will make a decision about allowing Wilken to fulfill his contract (and perhaps then make his own decision about an extension).

It is, however, also possible – if, perhaps, unlikely – that this is one of those “votes of no confidence.” By extending Fleita, effectively telling the next GM, “I don’t care what you do with anyone else, but we’re keeping this guy,” and then not extending Wilken under very similar circumstances, Ricketts could be communicating two things: (1) he likes Wilken, but doesn’t “like him, like him,” and is unwilling to go to bat for him in the same way as he was for Fleita; and (2) he will not stand in the way of the next GM if that guy wants to replace Wilken.

Whatever the explanation, I’m pretty ambivalent about the outcome. If Wilken stays, great. If Wilken is replaced by the new GM’s guy (assuming I am happy with the GM hire), great. I just hope that this isn’t a matter of Ricketts¬†kowtowing¬†to the hataz who said he’d overstepped his bounds by extending Fleita.

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