NCAA Basketball: NCAA Tournament-South Regional-Purdue vs Virginia
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Looking at the list of active college basketball coaches with the most wins, it's pretty easy to predict that at least a few will reach the exclusive 800-victory club inhabited by the game's legends.

John Calipari and Bill Self already have more than 700 wins apiece, and it's not hard to see guys like Tom Izzo, Jay Wright and Rick Barnes reaching the milestone as well, depending on how long they want to coach. Gonzaga's Mark Few will also cruise to 800 wins, assuming he coaches another eight years.

But who among the sport's younger crop of coaches has the staying power to reach the 800-win club?

For this week's dribble handoff, Matt Norlander conjured up an interesting prompt: Which coach with fewer than 400 wins is our best pick to have a chance at 800 wins?

It's tricky, because most coaches with 300-400 wins are going to need close to 20 more years of success to reach 800, and any number of factors could derail their pursuit. Elite coaches are poached by the NBA, they get hit with sanctions for breaking rules, they plateau and fizzle out. Sometimes, they retire just short of 800 — looking at you, Lute Olson.

Here are our predictions for which coaches in the sub-400 win category will avoid enough of those pitfalls to reach the 800-win category.

Tony Bennett, Virginia

This is something I'd never spent one second thinking about before the question was posed. But now that I've spent 15 seconds thinking about it, I'll go with the obvious answer.

Virginia's Tony Bennett.

Bennett is 51 years-old with 346 career victories. He's averaged 29 wins per season over the past seven years (even with last season getting cut short because of the COVID-19 pandemic). So if he continues to average 29 wins per season for the next 16 seasons, he'd hit 800 victories at the age of 67. And considering Bennett coaches in a league where men are routinely coaching into their 70s — Syracuse Hall of Fame coach Jim Boeheim is 75, Duke Hall of Fame coach Mike Krzyzewski is 73, Florida State coach Leonard Hamilton is 72, North Carolina Hall of Fame coach Roy Williams is 70, Miami coach Jim Larranaga is 70 — there's no reason to eliminate the possibility of Bennett doing the same. So the only thing between Bennett and 800 victories is … the NBA. Put another way, as long as Virginia can keep Bennett from someday moving to professional basketball, he'll eventually retire very high on the all-time wins list and join Boeheim, Krzyzewski and Williams in the Naismith Memorial Hall of Fame. -- Gary Parrish

Mick Cronin, UCLA

So, the Tony Bennett nomination from GP is a good one. I think he's the strongest candidate -- but I also think there is a real chance Bennett goes to the NBA in the next five years if he gets to another Final Four with Virginia. That's obviously no given, but UVA has a top-10 team for sure next season, so keep an eye out. I'd love to believe Bennett's a college hoops lifer, but I think we need to see him make it to 2025 in college hoops to be sure he takes the Jay Wright path. 

Now, some irony. Because those who listen to the Eye on College Basketball podcast know there is one coach my colleague Gary Parrish holds in higher esteem than all others: Michael Walter Cronin. And so here I find myself with a gift. Cronin is absolutely on the short list of candidates for this specific question. He's 49 years old, he has 17 years of head-coaching experience and he's tallied 384 wins. The man has made the NCAAs in 12 seasons and it would've been 13 with a 2020 tournament. 

Cronin's career wins average per season is 22.6. Let's round that up to 23 in a normal year, as UCLA probably would've had two or three more wins minimum last season. Cronin's definitely a college hoops lifer and I don't see him retiring for at least 17 more seasons. So we double his win total on average, putting him at 768 — and then you factor in that he's coaching a traditional blueblood in a talent-rich area. Cronin got the UCLA job in part because he took Cincinnati to nine straight tournaments, which amounted to the sixth-longest tournament streak in the sport at the time of his departure. 

And even if things ultimately go sideways and Cronin doesn't stick around at UCLA for a decade, his next job will still be a head-coaching one. He's the best blend of relative youth, good win total already, proven track record and being well-positioned at a high-level job. -- Matt Norlander

Scott Drew, Baylor

This shocked me to my core: Scott Drew is just 49 years young and already has 364 career wins. Then this shocked me even more: That tracks on a similar pace at a similar age with the likes of Eddie Sutton, Bill Self and Rick Pitino -- three Naismith Hall of Famers who are hailed as some of the best and brightest tacticians and motivators in the game.

Scott Drew is absolutely in the same tier. He revived a near-dead Baylor program from the doldrums of disaster nearly two decades ago and turned it into a force not only in the Big 12, but nationally. And, if not for a pandemic, it's possible we could be addressing Drew as national championship-winning coach Scott Drew.

Drew has the returning core of a preseason No. 1 team in 2020, too, and his 10-year outlook is as bright as any coach with fewer than 400 wins. Between what he has returning, the recruits he has on the way and the obvious ability he's shown of sustaining greatness, he's perhaps the safest and most obvious pick in this category who can easily get to 800 career wins. -- Kyle Boone

Matt Painter, Purdue

My comrades selected the three trendiest picks for this prompt, but I took Matt Painter because of his staying power at a school that produces consistent winners while avoiding NCAA scrutiny. If Painter coaches Purdue for another 20 years -- and he very well could -- the Boilermakers will have had two head coaches during a 60-year span between 1980 and 2040.

Painter, 49, is chugging along at 22.5 wins per season in the 15 years since he took over for his mentor Gene Keady. If he keeps that pace up, Painter will reach 800 wins around age 69 or 70. But he'll likely get there even sooner. Before a 16-win campaign last season, the Boilermakers averaged 27.3 wins per season over their previous four seasons. 

Purdue is the perfect place for Painter to quietly climb the all-time wins list. There are expectations and resources, but they come without the intense pressure of a blue-blood program. It's also Painter's alma mater, so it's easy to see him sticking it out long enough to reach 800 wins. -- David Cobb