From what I remember, I think a Richter-for-Joseph swap was also a part of the trade. If it was just Kovalev for Shanahan, then I agree he should've done it.
Richter for Joseph was something he tried to do, but failed.
Kovalev for Shanny could've been done had he thrown in Matteau, but no, he held on to Matteau until dealing him for 4th liner Ian Laperriere who spent his career getting a consistent 18-23 points per season.
The worst part of it was that Shanny desperately wanted to play for the Rangers his whole career. He would've been among the all-time great Rangers had he come to the Rangers 10 years before he did.
Richter for Joseph?!! If Smith ever though about that, then he must've been put of his mind. Yeah I agree he should've gotten Shanahan when he had the chance. He probably would've helped them a lot in the conference finals vs. the Flyers.
Neil - like almost all GMs - had both his ups and downs. He had one smashingly successful draft, several decent ones, and several miserable ones. He made several good deals, a number average ones, and several disastrous ones. He made a couple of good coaching decisions and a couple of poor ones.
As a manager of talent - trades, drafts - an adequate GM, nothing more. Delivering the hardware elevates his career.
Ironically, the current Rangers still owe Neil Smith one great debt of gratitude, that being hiring Martin Madden and promoting him to Director of Scouting. Why does that matter? Because Madden ran the 2000 draft, the one that yielded us the goalie who limited Ovechkin and Co. to two goals tonight.