Have you ever made a decision that made sense at the time? However, two hours, days, weeks, or months later, the logic nor emotion seem particularly astute. What was supposed to happen didn't, and the best-laid plans are far from that.
Similarly, baseball moves that seem sound can become less so with the passage of time, and a few unexpected surprises. That's how I see the Gray Fenter Rule 5 claiming in early December from the Orioles, as of now.
Many baseball fans are understandably "give me results now" types. I tend to have a bit of a longer view, which normally ranges me from "unpopular" to "counter-intuitive." The December Rule 5 Draft is normally a scouting call, often looking for a down-the-line payoff. For instance, Hector Rendon was a borderline train wreck as a rookie in 2013, but had several good years for the Cubs and claimed the save when the Cubs eliminated the Cardinals in the 2015 postseason. To say the Rule 5 Draft can't help long-term for success is absurd.
With the selection of a Rule 5 player comes a few understandings. He might be initially ill-equipped for MLB success. He might get returned to his prior team for half the purchase cost. In the case of Gray Fenter, though, he must receive a "valid look" in spring training. As the Cubs look to create roster space for Jake Marisnick and Brandon Workman, designating Fenter for assignment isn't an option. He’s on the 40-man roster until mid-March, like it or not.
For Cubs President of Baseball Operations Jed Hoyer, slow-playing a long-term relief piece might have made sense two months ago. However, with Workman needing a roster spot to begin ramping up with the team, Fenter likely seems extraneous for the next month. It's unlikely he can get in enough good outings in a condensed pre-season schedule (by innings, if not games) to be blocking Workman or Marisnick this weekend.
As such, look for a DFA of a reliever or infielder soon. The other conceivable (though not desirable) option would be to parcel Fenter to a team with a more available 40-man spot, sending a fringe prospect to get the team to bite. Perhaps Hoyer mis-estimated the Reds or Brewers commitment to the season. Or, the pro scouting department is particularly bullish on Fenter.