I would like to tell you a true betting story — one with many ups and downs that takes place over the course of 10-plus years. It all started in 2007 when I was still in college. I met a friend for drinks and some April baseball degenerate weekday action at a bar (McFadden’s) in Washington, D.C. With March having recently ended, the topic of conversation turned to the idea of a No. 16 seed winning a game in the NCAA Tournament.

The Setup

Our mental state: Trending away from sober

The bar argument: If/when a No. 16 seed would ever beat a No. 1 seed

My position: At least one No. 16 seed would win before 2020

His position: No. 1 seeds would go 52-0 between 2008 and 2020

The stakes: $10,000 at even money

Additional Background

A $10,000 bet might seem aggressive for college kids, but remember this spans the course of 13 years.

For a few years we stayed in touch after graduation, texting more often during March when the 1-vs.-16 matchups tipped. Those conversations usually involved him gloating and telling me about what he was going to spend his $10,000 on (all in good fun).

 

However, over time, the bet lost its luster in regards to our banter, as we both knew how much longer we still had before we could settle anything. Our friendship eventually faded completely away, as college connections tend to do over time. We even stopped sharing superficial texts during the tournament and actually haven’t talked since around 2011. More on that later.

I still always got excited every year when the 1-vs.-16 matchups would be revealed, anxiously waiting for that one potential matchup that could give me a glimmer of hope. That hope always turned to despair by the end of March, although there were some close calls along the way. Let’s take a closer look at the ride since 2009.

2008-11: Bet Regret

Over the course of the first four tournaments after we locked in our wager, not a single No. 16 seed lost by even single digits. The No. 1 seeds went 16-0 with an average margin of victory of 29.25 points. In fact, only one of the 16 games was decided by fewer than 16 points: Pittsburgh vs. East Tennessee State in 2009. That Pitt team, led by center DeJuan Blair, held only a 59-57 lead with 4:28 left before pulling away late. If only ETSU didn’t miss 12 free throws.

After the 2011 tourney, No. 1 seeds were 108-0 since the tourney expanded to 64 teams in 1985. Even with the Pitt scare, I started to question whether I had made the right bet. I started to think that maybe the talent gap between the top and bottom teams in the tournament was growing. There hadn’t really been a true scare since Purdue’s two-point win over Western Carolina in 1996.

2012: Glimmer of Hope

I’m back, baby! My faith was restored after watching No. 16 seed North Carolina-Asheville lose by just seven points to No. 1 seed Syracuse in the very first 1-vs.-16 matchup of the 2012 tournament. UNCA led that game at the half and kept it close throughout despite some egregious officiating mistakes in both halves. The two that stick out the most are the shot-clock violation at the end of the first half and an uncalled five-second violation in the final minutes.

 

2013: ONLY A MATTER OF TIME

Now we’re talking! Two separate 1-vs.-16 matchups were decided by single digits in the same year. Those included:

  • No. 1 Kansas vs. No. 16 Western Kentucky: Another No. 16 seed held a halftime lead, and this was on the same day that No. 15 seed Florida Gulf Coast upset No. 2 seed Georgetown. Kansas, led by guard Ben McLemore, eventually pulled away for a 64-57 win despite not making any 3-pointers (0-6).
  • No. 1 Gonzaga vs. No. 16 Southern: This one felt close. Southern, which trailed by three points at the half, cut the Zags’ lead to 54-52 with just over five minutes remaining. Gonzaga, led by Kelly Olynyk, would eventually hold on for a 64-58 win.

No. 1 seeds did ultimately improve to 116-0 all-time against No. 16 seeds, and I still didn’t have a winner after six tournaments, but I now believed more than ever that a No. 16 seed would win at least once in the next seven tournaments.

 

2014: More Momentum

More promising signs in the 2014 tournament. Three of the four 1-vs.-16 matchups were decided by no more than 12 points, including Weber State’s single-digit loss to Arizona. (Albany lost by 12 to Florida, and Coastal Carolina lost by 11 to Virginia).

2015-17: Uh Oh

Not a single 1-vs.-16 matchup was decided by fewer than 14 points over these three seasons. No. 1 seeds now sat at 132-0 against No. 16 seeds in the history of the tournament, and their margins of victory had grown over the past few seasons. I had only three tournaments left to get a win. What a stupid bet!

(Still no communication with my friend in over five years.)

2018: I Got a Feeling

I had a more optimistic feeling heading into this year’s tournament mainly because I thought Penn had a shot against Kansas. The Quakers were under-seeded at No. 16, and one could also argue that Kansas graded out closer to a No. 2 seed. (Although the Jayhawks certainly deserved a No. 1 seed.) I always envisioned the first potential No. 16 seed win occurring in a matchup between an under-seeded dog and an over-seeded favorite, so that on paper it would be a No. 16 beating a No. 1 but in reality it would feel more like a No. 15 beating a No. 2, which we’ve seen happen four times since 2012.

Penn came out in that game and built a double-digit lead.

HERE WE GO!

THIS IS IT!

(false alarm)

Kansas went on a patented No. 1 seed type of run to take a seven-point lead into the half. The Quakers would hang around in the second half, but Kansas eventually pulled away late for a win and cover. Those free throws. (Penn shot 5-for-14 from the stripe.)

At that point, I thought there might not be another No. 16 seed with as good of a chance of winning as Penn, which was listed as only a 14-point underdog. That was the shortest spread in a 1-vs.-16 matchup since 2005 (Oral Roberts vs. Memphis -10.5). Would another 13 years go by before we get a spread that short?

Later that night, No. 1 seed Villanova destroyed No. 16 seed Radford by 26 points. I had only 10 games remaining through the end of the 2020 NCAA tournament to get this done.

Last Shot of 2018

First up was No. 1 seed Xavier against No. 16 Texas Southern: X won fairly comfortably (by 19 points), which meant that No. 1 seeds had improved to 135-0 all-time against No. 16 seeds.

The last chance in 2018 came on Friday night between No. 1 overall seed Virginia and No. 16 Maryland-Baltimore County.

Let’s rewind a few hours to earlier in the day Friday afternoon. I did start to get an odd feeling about this this game the more I looked at it.

 

I bet the Retrievers +21.5 and started to think they could make this a game.

Okay, back to the game. UMBC came out with confidence, but the first half ended with an ugly 21-all score. Regardless, I believed midway through the half.

 

I still don’t believe what happened next. UMBC came out and ran the No. 1 overall seed out of the gym. The Wahoos never really made a run. The 21-point underdog had made history with a 20-point win. The No. 16 seed put up 53 points in the second half against a team that led the nation in scoring defense, allowing just over 53 points PER GAME.

10 GRAND!

No more nightmares about a No. 16 seed finally winning in 2021. Absolute euphoria. I was on cloud nine watching the Retrievers pull off something I had wanted to see my whole life, especially since 2008.

But, wait. 10 GRAND?

The Dilemma

The main problem I now face is retrieving my money (pun intended). I do have some reservations about reaching out to an ex-friend I haven’t talked to in six or seven years just to ask for $10,000 on a bet we made over 10 years ago. I first need to find out how to get in touch with him, as I have no idea where he lives or what he is up to. (I don’t do the whole non-Twitter social media thing.) What kind of financial shape is he in? There are many questions.

I ultimately need to determine if he would have made me pay in 2020 if he had won, which I will never be able to know for sure. A bet is a bet, and I always pay mine, but this seems a little more complicated. Whether I ever get part or all of the money, it was still an enjoyable ride and I’m glad I got to witness history. I will always be part Retriever.

Photo credit: Peter Casey-USA TODAY Sports

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