Toews for his career.
Gretzky played 20 seasons and won 4 Stanley Cups.
That's 16 seasons where he didn't win the Cup.
And he won the Cups on a historically stacked Oilers team.
Toews can give you at least 10 years of great play, he might not be a top 5 player in the league even during his prime but he's demonstrated he can be the 1C on a Cup-winning team.
Yeah. This is pretty much how i look at it. Gretzky, even in his prime is far from a "guarantee" of anything. After which, you're left with nothing no matter what in this hypothetical.
Compared to a guaranteed decade of having a #1C caliber player to build around and try to make something happen. That's 10x the "chances" at making that magical run to the Cup, with a key piece permanently in place. It also doesn't preclude the notion of multiple potential Cups in that span, as the Gretzky option does.
The only way the Gretzky option makes any sense to me, is if you currently have a team that you believe is that 1 piece away from being virtually unstoppable. But even then...your single cup run aspirations could instantly be dashed if a top defenceman, or a starting goaltender goes down in the first round and you completely wash out. Winning a Cup is too fickle and unpredictable to go "all-in" on one singular run like that. I want 10 kicks at the can instead.