I would think that wooden would have a lot of trouble competing in the modern era when 100+ programs have the desire and resources to win.
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What Wooden would have trouble with would be the lack of discipline and work ethic in many of todays players who try to get by on superior physical ability. Wooden may have had great players, but his attention to detail and fundamentals made most of those players even better. He was innovative in his approach to practices and what and how he taught the game of basketball. Many coaches followed his ways, but Wooden was so disciplined and patient to let his methods succeed, that many who tried/try to emulate him don't have the patience or discipline to allow those methods to work. Wooden wasn't so rigid as to not be able to adapt to the game, but rigid in that he didn't deviate from his methods.
Wooden could go back to any of his practices in his career and pull out the practice plan and show you what he worked on that day. His practices consisted largely of drills working fundamentals (help and recover, cutting off baseline, boxing out, outlet passess, running the break, v-cut to get open, getting an angle for an entry pass, dribbling, passing etc...) . The fundamentals learned in these specific drills were all parts of the bigger piece, playing the game. His philosophy was that if you didn't learn these basic fundamentals you would have a hard time playing the game. And he was right. The lack of basic fundamentals at the modified level and even much of the high school varsity level is staggering, the fundamentals just aren't getting stressed and the younger levels (its more about physical ability and kids jacking 3's). Watch a modified game and see how many layups get missed with the strong hand, let alone kids even attempting to shoot a layup with their weak hand.
Fortunately I played in a grammar school program in the 70's with a coach that was a Wooden disciple who taught the fundamentals and stressed them in practice with the same kind of drills Wooden used. If you didn't learn how to play fundamentally sound you wouldn't play, let alone make the team. We rarely lost even at the varsity level, and not because we had superior athletes we didn't but we were superior basketball players fundamentally.
The other thing about Wooden was his competitiveness, what alot off people I talk to don't realize was that he was an All-American in college and was a player of the year.
Would Wooden win like he did in the 60's and 70's, probably not but he would still be a successful coach and one of the best in any era.