Last summer, I was somewhat opposed to the rumored Heatley deal, though not as strenuously as some. This season, all considered, I think I would tend to be more in favour of a similar deal involving Spezza.
If the trade package rumoured in the Heatley deal summer were enough to land Spezza this summer, the Oilers would be giving up a little bit less value now than they would have been then. Yes, Penner had a very good season last year, but he's only got 2 years left instead of 3. Cogliano's ELC is over(and he didn't appear to take any huge steps forward in development), leaving him an RFA under team control for 4 years instead of 5. Smid is signed for one more year, after which he'll be a UFA in the summer of 2013. In exchange, the Oilers would get a 27 year old C at a 7.0 mil cap hit vs. a 28 year old LW at a 7.5 mil cap hit, both signed for 5 years at the time of the deal. Pretty similar players that way, but I like watching Spezza more. Very informed and educational, I know.
If you could get him with Souray in the deal and keep Penner, that would be even better, but I'm not sure there's a deal to be made with Ottawa in that case. At least, not one that doesn't keep all the players Edmonton would presumably want to keep. I don't know that OTT goes for a Souray, Nash, Cogliano, choice of O'Sullivan/Nilsson, EDM 2010 2nd (31 OV) for Spezza and Cheechoo deal, and I'm not sure if EDM can do any better without giving up players they'd prefer not to give up in a rebuild.
An additional reason that I potentially like the timing of such a deal more with Spezza than I did with Heatley is the prospective outlook of the team in a year or two. Even though the team was significantly worse in the 2009/10 season than in 2008/9, I believe an argument that the team is in better shape looking forward than it was one year ago is fair, if you feel particularly confident in Eberle, Paajarvi, and Hall/Seguin as prospects. At this time last year Eberle looked like a good prospect, but since then has had as good an individual season as one could have been hoped. Paajarvi slipped in the draft to #10, EDM picked him up, and he had a great 18 year old. I don't know what the expectations were for EDM's 2010 1st round pick a year ago, but I doubt if it was the #1 overall pick. If someone tried to sell me that Edmonton's best opportunity to compete over the next 5 seasons would be the 2011/12 season, with Eberle, Paajarvi, Hall, Gagner, Penner*, Hemsky all still potentially in Edmonton on relatively cheap contracts and, barring buyouts, Edmonton will open up 7 million dollars in cap room between Nilsson, O'Sullivan, and Moreau, none of whom figure to be deals at their current cap hits.
Ok, upon further review, maybe these arguments are a bit tenuous. I can see why the team both would, and wouldn't, want to make a "win now", "whale hunting"** move, and certainly concede it could blow up in Edmonton's face, especially if Spezza can't stay healthy going forward**. All that said, mark me down as philosophically in favour of trading for Spezza, given a deal that doesn't get rid of any players the team is planning to build around.
* assuming you can trade for Spezza while keeping Penner.
** I don't know that I like terming a potential trade for Spezza as a "whale hunt", I think that worked better for the Heatley situation than this. It seems far less likely that there would be ano indefinite timeline to this like the Heatley situation; if he's going to be traded it would probably happen at or before the draft and should be done with by the time free agency starts at the latest given Spezza's impending NTC/NMC.
I'm not sure what counts as "whale hunting" these days for the Oilers. Is it acquiring any big name player making big name money? Obviously no one's going to be saying the Oilers shouldn't trade 31 and 48 OV for Crosby given the opportunity, even though that doesn't count as building through the draft the traditional way.
*** This is an issue I should have touched on earlier. Any acquiring team would want to take a pretty good look at his injury history, I don't know much about it offhand but he's missed 10+ games in half his full NHL seasons.