MaxUFC
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He will lead Caps to Stanley Cup. No Question about that.
Maybe he finally win it at near end career of his playing in 2028 (his contract signed for next 20 years) like my idol, Ray Boruque won at his final year with Colorado.
Since Ovechkin will have to get thur bright future team Pittsburgh Penguins's corps : Sidney Crosby, Evgeni Malkin and Marc-Andre Fleury.
Crosby would win more Cup than Ovechkin.
One problem : not easy to win Stanley Cup at all and tough playoff any sport's playoffs.
BTW, I am big fan of Crosby and Ovechkin and gotta see them for next 15 years.