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Worst bets of 2020: Reliving our biggest regrets

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There are bad beats and then there are bad bets.

The former leaves you angry and bewildered. It makes you want to rip off your shirt and strangle the TV with it, but the feeling is fleeting and life goes on.

Bad bets run deeper. They are humiliating and humbling, and leave you flustered and insecure. You don't feel wronged, but rather just wrong. They have you second-guessing everything and doubting your every move.

Here are the bets we made this year that had us re-evaluating what we thought we knew about sports.

Arizona Diamondbacks, everything

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Imagine looking at the Los Angeles Dodgers and San Diego Padres and thinking, "Nah, I prefer the Diamondbacks."

It's unbelievable how wrapped up in this garbage team I was. I bought National League West, NLCS, and World Series futures. I had their win total over and bet them to make the playoffs. MLB expanded its postseason field to 16 teams and they still couldn't make it.

I was convinced Madison Bumgarner and Starling Marte would push an already strong roster over the top. Bumgarner finished the year 1-4 with a 6.48 ERA and the club traded Marte when it realized the season was lost. From Aug. 19 to Sept. 9, the Diamondbacks went 2-18.

As a glutton for punishment, I also bet Ketel Marte to win the NL MVP and drafted him in all of my fantasy leagues. He smacked two home runs and batted in a measly 17 runs in 45 games.

Never trust a snake.

- Alex Moretto

Carolina Hurricanes to win the Stanley Cup

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I loved everything about the Hurricanes: the young talent up front, the defensive depth, the swagger, the coaching ... the fact they beat the Toronto Maple Leafs with a Zamboni driver as their goalie.

Carolina was excellent at generating offense - second in expected goals for and high-danger scoring chances per 60 minutes - and controlling the balance of play, sitting first in Corsi for percentage.

I bought in February (40-1), again after the trade deadline (20-1), and then again before the start of the playoffs (40-1).

Then, Andrei Svechnikov got hurt and they were bounced by the Boston Bruins in the first round.

- Moretto

Dallas Cowboys over 9.5 wins

Kevork Djansezian / Getty Images Sport / Getty

This was my favorite win total. Most respected bettors I talked to were on board, too.

The Cowboys lost seven games before their bye week. Only Mike McCarthy could take a Super Bowl contender and ground them into the dirt.

- Alex Kolodziej

Matthew Wolff (+20000), Rocket Mortgage Classic

Stacy Revere / Getty Images Sport / Getty

I don't often bet golf outrights, and I may never again after what occurred at the Rocket Mortgage Classic.

A friend told me Wolff was serious value at 200-1. Though normally I wouldn't bet a hunch, I figured I'd dabble.

Wolff had a three-stroke lead entering Sunday, at which point I was already deciding what color yacht suited me best.

Naturally, I broke the golden rule by telling my dad on Sunday morning that I had Wolff at 200-1. Six brutal hours later, he wound up losing by three strokes.

To make matters worse, my dad now calls me the day before every tournament asking me who I like. I don't even bet golf!

Moral of the story: don't ever tell your family who you bet.

- Kolodziej

North Carolina to win the NCAA Tournament (+1400)

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The Hurricanes weren't the only team from Carolina to disappoint us this year. Last summer, when the Tar Heels were dealing at 14-1, I had to take a shot. They were on the verge of signing high school phenom Cole Anthony - who projected to be even better than Coby White from the year before - and had a loaded frontcourt, to boot. I figured the price would only get shorter from here, right?

Boy, was I ever wrong. North Carolina won its first five games in uninspiring fashion before injuries derailed the season. However, even a healthy squad would have struggled to make the tournament, let alone win it. By the time the season ended in March, UNC was 14-19 - the fourth-worst record in school history and worst during the Roy Williams era.

The only consolation here is the bet was never actually lost as the NCAA was forced to cancel the tournament. But my shame for making it in the first place still lives on.

- C Jackson Cowart

San Jose Sharks to win the Stanley Cup (25-1)

Brandon Magnus / National Hockey League / Getty

When Kevin Labanc signed a discount deal to stay in San Jose for another shot at winning with the Sharks, I was all-in.

A player signs for cheap and I tout his team to win, because, apparently, it lends itself to a "united locker room" and "winning culture."

Yeah, that aged well.

- Moretto

Utah Jazz, everything

Melissa Majchrzak / National Basketball Association / Getty

I was all-in on the Jazz last year and had every reason to be. A season after winning 50 games, they added Mike Conley and Bojan Bogdanovic and still opened to win just 52.5 games. Why not bet the farm, right? And that I did, betting Utah from every angle I could find: over 52.5 wins, Donovan Mitchell to win MVP (40-1), Quin Snyder to win Coach of the Year (+650).

Just marvel at those last two. I bet on Mitchell, who finished with fewer win shares than Dwight Howard, to win MVP. I bet on Snyder - whose team ended the year on a 12-15 run before ultimately ushering in the coronavirus into the league, leading to the NBA's suspension - to win Coach of the Year. That's something I actually did.

Unfortunately, I can't say I learned my lesson. Mitchell at 85-1 to win MVP, anyone?

- Cowart

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