Kirk rules.

hwm

Star Trek tag team wrestling match
 

Kirk would definitely win. In addition, Picard's too much of a gentleman, he'd let Kirk win thinking that means the Federation wins.

In addition, the Borg could never assimilate Kirk. He would have assimilated them, and made some time with the Borg queen to boot. What can you say, he's a force of nature. I could see Kirk, Q, and the Borg queen all getting together for a friendly game of cards.

You old timers might remember Kirk had a Q like problem by the name of Trelane. Kicked his butt.

Then Kirk will turn it into a game of strip poker, he always has to get the woman, green or otherwise.

Kirk wins.

He had Picard holding logs for him and doing his scrambled eggs in Generations.

That's just hero worship, and Picard needed Kirk.

Picard is smarter and more experienced, but that might be why Kirk shot first and destroyed Picard. Of course, that is silly if only because Picard's starship would easily withstand anything Kirk's could throw at him.