3C. All the good teams in the East have tremendous center depth.

Why even bother trading at the deadline this year? Washington, Tampa and Toronto are stacked and to get to the cup you will have to beat 2 of them. You have 1 player that matters becoming a UFA and Chara isn't going to any other team. I'd play it smart and save your pick and prospects for next years TDL. Unless you get a chance to get a really good player and not someone to just fill a hole. Then be aggressive in free agency. The teams I mentioned above will all look different next year especially if one wins a cup all their UFAs offers will rise 10%-15% because they've won a cup.

This is your best ACGM yet

While I don’t think anyone beats Tampa, unless they add a d man, I don’t think the leafs can beat the bruins in a series

I agree with that completely. Tampa has even said publicly how different their team will look next year. I watched Montreal v Boston tonight and every time I watch Pastrnak he impresses me going in 1 on 2 and he splits the D and makes it look easy.

To answer the question. The 2RW. You can play that second line 20+ minutes a night in the playoffs. The 3rd line probably 14-15.

TB is over rated. Those little wingers get put into the boards and they are done. Just like washington did to them. Every year "oh tb is the best team" and like every year it's a metro team playing for the cup. I don't see it changing this year. Leafs don't have the goal tending with anderson. Boston has no secondary scoring. TB is soft when people are trying to make you not want to play.
While the Atlantic will be having track meets, the metro will be trying to kill each other in the boards. I don't think there are any teams in the Atlantic that can enter the thunder dome and leave alive.

Second line winger.

That balances your scoring and increases the impact of both top two lines. Boston can make a trade for a skilled winger without decreasing the quality of this year's team AND without creating a prospect deficit.

You're assuming this Tampa team is the same team health wise and performance wise as the one that will be in the playoffs. It's extremely hard to go wire to wire and win the Cup. Since '85, 8 teams have won a President's Cup and a Stanley Cup. You have a 19% of getting knocked out in the first round vs. 25% a chance of winning a Stanley Cup.