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In the summer of 2008, Andrej Meszaros was an RFA after three productive seasons in Ottawa. Sens were up against the cap and didn't have the space to meet Meszaros' asking price.
Meanwhile Tampa Bay had new ownership fresh off of drafting Steven Stamkos. After trading away Dan Boyle, they wanted to get a young established defenseman who could be a cornerstone with Stamkos. So they decided to target Meszaros.
The rumor was that Tampa and Meszaros' agent had agreed to terms but they couldn't sign an offer sheet because Tampa had previously traded its 2009 3rd rounder which was a required part of the compensation. Allegedly Tampa tried to get it back from Pittsburgh, but Ray Shero thought he was doing the honorable thing by not trading it back and being an enabler.
Ottawa was a season removed from a SCF appearance so they understandably thought they were still a contender. So instead of just accepting Tampa's 2009 1st and 2nd via trade, they wanted an NHL D to replace Meszaros. Right before training camp started, Ottawa agreed to trade Meszaros to Tampa for Filip Kuba and San Jose's 2009 1st.
Tampa remained in the basement as Meszaros' offense would dry up. After a couple seasons, newly appointed GM Steve Yzerman would trade him to Philadelphia for a 2nd round pick.
Meanwhile Ottawa quickly dropped from contender status and would miss the playoffs. Kuba seemingly played decently but he was already in his early 30's when he was traded. Sens GM Bryan Murray would deal San Jose's 2009 1st for Mike Comrie and Chris Campoli.
Had they accepted Tampa's 2009 1st, Ottawa could have had Victor Hedman. That Tampa ownership lucked out by its own lack of foresight; They'd end up selling the team after just two years. I can't help but notice that bad owners seem to be a common thread in these bad trades.