[Six Degrees of Separation]

Picard met the X-men in a Star Trek/X-Men crossover written by Scott Lobdell. Storm met Iron man during the last part of the onslaught saga.

The Lobdell crossover was the one I had in mind, but either way seems quite valid.

Phazer

[Six Degrees of Separation]

Spiderman guest starred in the US Transformers #3, fighting alongside Gears, though he also said hello to Prime, so I guess you could just connect it that way.

Spiderman to Gambit can be done at least a half dozen times over the years.

To say there's a connection is one thing, to show it is another. Please show/layout the connection from Prime to Gambit.

Fair enough. Spiderman team up #5 features Gambit. Or Adventures of Spiderman #3.

You could also use Circuit Breaker, who I believe turned up in Secret Wars II (not X-Men, as I first said).

Mine is Jean Luc Picard to Iron Man.

Phazer

[Six Degrees of Separation]

Spiderman guest starred in the US Transformers #3, fighting alongside Gears, though he also said hello to Prime, so I guess you could just connect it that way.

Spiderman to Gambit can be done at least a half dozen times over the years.

Phazer

[Penny Arcade]

Hmm... penny arcadey....

Phazer