Press Break Mr. March Madness First Four

Eight NCAA Tournament standouts vie for the No. 16 seeds in the inaugural Mr. March Madness bracket.

The inaugural Press Break Mr. March Madness competition begins, as the NCAA Tournament has for a decade-and-a-half, with the First Four.

Each of the bracket’s quartet of opening matchups feature potential Cinderellas, each vying for inclusion as Mr. March Madness 16 seeds.

But don’t let their seeding mislead you: Each of the eight are true legends of the season, each for their own reasons as broken down in the matchups below.

For the complete Mr. March Madness field, please visit the below. To vote on the First Four matchups, click the button at the bottom of this entry.

Matchup 1: Wally Szczerbiak, Miami (OH) vs. Billy Donovan, Providence

Wally Szczerbiak’s Tale of the Tape

• NCAA Tournament Appearances: 2 (1997, 1999); 4 games played

• Furthest Run: 1999 Sweet 16

• Key Tournament Stats: 24.3 points per game, 6.3 rebounds per game, 2 assists per game, 56.5% percent 3-point shooting (

• Postseason Accolades: 1999 All-Regional Team

While the 2025-26 Miami Redhawks vie to make history with a perfect regular season, the standard was set in Oxford over a 15-year stretch from 1983-1999.

Arguably, Miami reached its peak of the run with a crescendo in ‘99, and Wally Szczerbiak played conductor.

Szczerbiak debuted in the NCAA Tournament with a muted performance in 1997, shooting 1-of-6 from 3-point range and scoring just seven points in a 1st Round loss to Clemson.

However, he bounced back two years later with an absolutely monster stretch that sent Miami to the Sweet 16.

Szczerbiak shot 18-of-33 from the floor — 5-of-12 from deep — on the way to 43 points in a 1st Round win over Washington. More than just how impressive this offensive onslaught was on its own is the added context that the Redhawks scored just 59 points in a one-point win.

That means coupled with his two assists, Szczerbiak was responsible for 79.7% of Miami’s points.

For the duration of the 1999 Tournament — which pit the Redhawks against each of the previous season’s two National Championship Game participants, Utah and Kentucky — Szczerbiak scored 24 and 23 points and dished out five and two assists. In total, he was responsible for more than 64 percent of Miami’s offense.

What’s more, he swiped five steals across the three games, grabbed 12 rebounds against Washington for a double-double, and pulled down another eight boards in the 2nd Round win over Utah.

Billy Donovan’s Tale of the Tape

• NCAA Tournament Appearances: 1 (1987); 5 games played

• Furthest Run: 1987 Final Four

• Key Tournament Stats: 22.8 points per game, 8.4 assists per game, 3 rebounds per game 2.4 steals per game, 63.7% 3-point shooting (14-of-22)

• Postseason Accolades: 1987 All-Regional Team

Before coaching Florida to back-to-back national championships in 2006 and 2007, Billy Donovan captained the 1987 Providence Friars to the Final Four. Their national semifinal appearance marked the first Final Four appearance in Rick Pitino’s career, and remains just the second Final Four ever for Providence.

Donovan was electric in all four Friars wins, beginning with a game for the ages in the 1st Round vs. UAB. He went off for 35 points — more than half of which came on 6-of-9 3-point shooting — and dished 12 assists to contribute to two-thirds of Providence’s total scoring in a 90-68 rout.

Donovan followed up with games of 25 points in a 2nd Round, overtime win over Austin Peay — which stunned a third-seeded Illinois team, many of whom were part of the Illini’s 1989 Final Four run — another double-double with 26 points and 10 assists in the Sweet 16 vs. Alabama, and 20 points with six assists, four boards and a steal against Big East rival Georgetown in the Elite Eight.

Donovan would have been a lock for a higher seed with a stronger Final Four performance, having shot just 3-of-12 from the floor for eight points in the loss to another Big East team, Syracuse. Still, he dished seven assists against the Orange to round out a Tournament approaching a double-double in the majority of games.

Matchup 2: Antonio Gates, Kent State vs. Draymond Green, Michigan State

Antonio Gates’ Tale of the Tape

• NCAA Tournament Appearances: 1; 4 games played

• Furthest Run: 2002 Elite Eight

• Key Tournament Stats: 18.8 points per game, 7.3 rebounds per game, 2 assists per game, 52.5% field-goal shooting (31-of-59)

• Postseason Accolades: 2002 All-Regional Team

I dove into Antonio Gates’ basketball career at length last summer, coinciding with the legendary San Diego¹ Chargers tight end being inducted into the Pro Football Hall of Fame. You can check it out below.

But, for a quick refresher, Gates powered his way into the national spotlight long before anyone could have guessed he’d be an NFL star with an impressive 2002 NCAA Tournament.

Gates improved with each Kent State outing, going from a modest 13 and four in the opening-round win over Oklahoma State, to 18 and nine with a pair of assists in the Round of 32 vs. Alabama.

His showing in a Sweet 16 win over Pitt really cemented Gates’ place in the pantheon of memorable March Madness Cinderellas, however. Gates went for 22 points, eight rebounds and four assists against a third-seeded Panthers team that won 27 games ahead of the NCAA Tournament.

Gates was great again in the Elite Eight loss to eventual national runner-up Indiana, finishing with 22 points, eight rebounds and a pair of steals.

Draymond Green’s Tale of the Tape

• NCAA Tournament Appearances: 4 (2009-2012); 15 games played

• Furthest Run: 2009 National Championship Game

• Key Tournament Stats:

• Postseason Accolades: 2010 and 2012 All-Regional Team

Of the Mr. March Madness First Four participants, Draymond Green is the only to play in a National Championship Game and alone in having reached multiple Final Fours. That alone could qualify Green for higher seeding than this play-in round, though his contributions in the 2009 and 2010 postseasons were more filling an important role than shining as a star.

To wit, he scored 16 points in his March Madness debut vs. Robert Morris, but posted single-digit totals the rest of the 2009 Tournament. In 2010, he grabbed a solid 32 rebounds in five games but only scored in double-figures twice.

The next two years, however, he achieved a feat no other NCAA Tournament participant has…at least officially.

Green is the only player ever to produce two triple-doubles since the milestone’s been recorded, going for 23 points, 11 rebounds and 10 assists — as well as four steals — in a 1st Round exit vs. UCLA in 2011.

Michigan State returned to the second weekend in 2012, with Green registering a 24-point, 12-rebound and 10-assist performance against Long Island. He followed up with double-doubles in each of the next two rounds, posting 16 and 13 boards against Saint Louis then 13 points and 16 rebounds in a Sweet 16 loss to Louisville.

Matchup 3: Lamar Butler, George Mason vs. Fennis Dembo, Wyoming

Lamar Butler’s Tale of the Tape

• NCAA Tournament Appearances: 1 (2006); 5 games played

• Furthest Run: 2006 Final Four

• Key Tournament Stats: 14.4 points per game, 6.5 rebounds per game, 2.5 assists per game, 1.5 steals per game, 1.3 blocks per game

• Postseason Accolades: 2006 All-Regional Team

George Mason’s improbable 2006 Final Four appearance is all the more unlikely considering the Patriots didn’t ride the otherworldly play of a single standout. This wasn’t a run akin to Davidson’s Elite Eight stretch two years later, with future NBA Most Valuable Player Steph Curry flashing the transformational scoring that helped reshape basketball for a generation.

In fact, Lamar Butler was not the first Patriot who came to find for inclusion in the Mr. March Madness field. That would be Tony Skinn, the current George Mason head coach whose leadership through the 2006 NCAA Tournament marked a redemptive story for the guard after he’d throwing a punch in the CAA Tournament.

Likewise, Jai Lewis had been the Patriots star during the regular season. But without Lamar Butler’s play, particularly in the Elite Eight win over UConn, George Mason would not have made history.

Butler cemented his place on the All-Regional team with 19 points against the Huskies, shooting 4-of-6 from 3-point range in his fourth consecutive game knocking down multiple triples. He also grabbed four rebounds and swiped a pair of steals, rounding out his second standout performance that Tournament against college basketball royalty.

He previous went for 18 points with a steal in the Round of 32 win over North Carolina.

Fennis Dembo’s Tale of the Tape

• NCAA Tournament Appearances: 2 (1987, 1988); 4 games played

• Furthest Run: 1987 Sweet 16

• Key Tournament Stats: 24.5 points per game, 8.5 rebounds per game, 5.3 assists per game, 45.8% 3-point shooting (11-of-24), 53.6% field-goal shooting (30-of-56)

• Postseason Accolades: 1987 All-Regional Team

The former Sports Illustrated cover athlete — at a time when that marked the apex for being in the athletic world’s public eye — earned his spot with a truly dazzling showing in 1987.

Fennis Dembo shot an eye-popping 7-of-10 from 3-point range, finished 9-of-13 from the floor, and went 16-for-16 at the foul line in a 2nd Round defeat of UCLA. Dembo’s long-range touch outpaced a counterpart who’d later become synonymous with the shot, Reggie Miller. Miller was 2-of-4 from 3-point distance on the way to 24 points.

In addition to his offensive eruption, Dembo grabbed nine rebounds and doled out six assists. He snatched nine rebounds in each of Wyoming’s three games in its Sweet 16 run, including in his 27-point effort in a loss to eventual Final Four participant UNLV.

Wyoming returned to the NCAA Tournament year later and lasted only one round, bowing out to an excellent Loyola Marymount team two years before the Lions’ famed Elite Eight journey.

Dembo nearly posted a triple-double in the 119-115 loss, going for 14 points, eight assists and seven rebounds.

Matchup 4: Casey Calvary, Gonzaga vs. Omar Samhan, Saint Mary’s

Casey Calvary’s Tale of the Tape

NCAA Tournament Appearances: 3; 10 games played

Furthest Run: 1999 Elite Eight

Key Tournament Stats: 13.6 points per game, 8 rebounds per game, 1.9 assists per game, 1.6 blocks per game

Postseason Accolades: 1999 and 2001 All-Regional Team

The foundation for Gonzaga evolving into college basketball’s least likely modern powerhouse was laid in 1999 with Casey Calvary at the forefront.

Gus Johnson’s famed call, “The slipper still fits!”, was born of Gonzaga’s 73-72 defeat of Florida in the 1999 Sweet 16. Calvary was an excellent running mate to Richie Frahm in that game, finishing with 12 points and five rebounds and delivering the most famed dunk in Gonzaga basketball history.

Calvary matured into Gonzaga’s go-to guy for Sweet 16 runs the following two NCAA Tournaments, which included double-doubles against Virginia and Michigan State in 2001.

Omar Samhan’s Tale of the Tape

NCAA Tournament Appearances: 2; 4 games played

Furthest Run: 2010 Sweet 16

Key Tournament Stats: 21 points per game, 8.3 rebounds per game, 1.5 blocks per game, 63% field-goal shooting

Postseason Accolades: 2010 All-Regional Team

At 6-foot-11 and a generously listed 260 pounds, Saint Mary’s big man Omar Samhan was a handful for opponents in the paint. He combined size with deft footwork in the paint to put on a captivating display in Saint Mary’s 2010 Sweet 16 run.

Samhan tipped things off with 29 points and 12 rebounds in a win over Richmond, setting up a Round of 32 Jesuit showdown with Villanova. The Wildcats were coming off of a Final Four run and seeded No. 2 East, but they had no answer for the big man from out West.

Samhan’s 32 points on 13-of-16 shooting from the floor was arguably the performance of the 2010 Tournament, possibly topping even Northern Iowa’s Ali Farokhmanesh².

Saint Mary’s best postseason ended with a loss to Baylor, but Samhan closed out with a solid 15 points, nine rebounds and two blocked shots.

1. It’s still San Diego to me, dammit!

2. I reference Farokhmanesh specifically because he was on the bubble for inclusion in Mr. March Madness. Consider this an opportunity to shout out his nine 3-point weekend against UNLV and Kansas, capped on the most famous shot-fake triple in recent memory.