Have to agree with Iggy on all counts. Connolly was signed for only 2 years. If he plays like expected, that's great. If he plays better, that's fantastic. If he struggles or gets injured, so be it.
I would't exactly refer to Lupul as being fragile. He had back surgery (which is now somewhat of a common thing) and wound up getting a blood infection due to the surgery that cost him an entire season. Anyone can get an infection.
The Leafs badly needed a center to play pivot between Kessel & Lupul. They went after Brad Richards, but the Rangers overpaid for him & Toronto went at what was available next. They got their man & didn't overpay to get him.
And now we have Steven Stamkos & the big contract he just signed. Tampa wanted to sign him for more years in order to lessen his cap value. Stamkos balked at their offer & settled for five years, which was a bit too much than what he wanted to sign for, but the $$ they threw at him made him accept their proposal. There are rumblings around the league as i'm writing this that there's a good chance he might get traded away. Personally, i don't think it's going to happen. However, the Bolts are just under the cap & they will have to clear up some salaries in order not to go under. A team like Tampa with no corporate backing & no fans going to the games cannot operate at the cap ceiling, or else they'll go under.
As for Andrei Markov, i might have liked to see him with the Leafs, but at much less money than Mtl is giving him & for less years. Maybe two, max. If he remains healthy & productive, the Habs will have got their money's worth. However, if he spends a good part of the season on the injury list once again, they'll be asking for Mini-Bob's head.