A Proxy’s Tale: Da Bears Unlucky for Potential Millionaire

^{A team of Boston bettors and their Las Vegas proxy (yours truly, third from left) pose with Circa casino owner Derek Stevens (far right) and their third-place check. (Photo: courtesy Circa)}

As a diehard fan of the Chicago Bears, watching Saturday night’s thrilling 31-27 comeback playoff win over the Green Bay Packers was one of the most memorable in my entire lifetime. But as a proxy for the biggest Las Vegas football contests, it was bittersweet to some degree considering the results of Chicago’s last two games of the regular season that ultimately ended up costing one of our clients the grand prize in the Circa Sports Million.

Derek Stevens’ Circa Resort & Casino plays host to the pick-five Million contest – with a guaranteed $6 million prize pool – plus the Circa Survivor and Grandissimo. The Million and Survivor cost $1,000 per entry while the high-stakes Grandissimo costs $100,000 to play. 

Stevens opened the Circa sportsbook to be the largest in the world back in 2020, so it is quite fitting that they are the home of contests that paid out a record total $31,618,000 in prize money. 

Because these football contests require in-person registration at one of the casino properties where Circa Sports is available Nevada (including The D, Tuscany and Silverton in Vegas, The Pass in Henderson and Legends Bay in Sparks, a proxy -- of which I am one -- is also required for entrants who reside outside Nevada and are unable to submit their picks within state lines.

“To think that there’s 31 million dollars of contest prizes going out, it’s really exceeded my wildest expectations,” Stevens said at the Circa check presentation ceremony on Friday. “Some incredible ups and downs – incredible season.”

Big Checks Awarded to Winning Handicappers

This past weekend was all about celebrating the winners of Circa’s football contests, and one of my favorite times of the year. Our proxy service has helped people win more than $15 million in prize money in the last 20 years by submitting picks for them, including over $2 million this season. Proxies are needed in order for out-of-state entrants to participate, and our biggest winners were Kujo ($1.125 million) in the Grandissimo and Sean’s Dolphins in the Million, with that entry taking home $400,000 for finishing third place overall.

It is hard to fathom being disappointed with winning nearly half a million dollars, although knowing just how close you were to taking home the top prize can put you in that state of mind. Second-guessing your decisions, replaying all the near-misses in your head and thinking about what you could have done differently can take a toll on you mentally. I honestly cannot imagine what our clients go through; as a proxy, we don’t handicap the games or make the picks yet become some of their biggest fans after doing our job.

Close Calls Costly for Sean’s Dolphins

One of the stories Stevens alluded to was told to me by our client Ed McKenna of Sean’s Dolphins, as he would have won the $1 million had the Bears simply covered the spread as 3.5-point road underdogs in a 42-38 loss to the San Francisco 49ers in Week 17 OR as 3-point home favorites in a 19-16 defeat against the Detroit Lions in Week 18. This same Chicago team that has defied the odds all season in record-breaking fashion lost on both occasions, leaving Ed to ponder what could have been if he had substituted the Los Angeles Rams in Week 18. He would have gone 5-0 to win the million dollars. 

It is worth noting that contest winner Coynehop had the 49ers in Week 17 for the biggest swing game of the season. San Francisco was two yards away from losing as time expired, setting the stage for a dramatic Week 18. Sean’s Dolphins needed Coynehop to have a losing week to have a shot, and that’s what happened with a 2-3 mark to give Ed a chance.

Prior to Week 18, Ed had texted me: 

“First time in a decade I don’t have one game I really like.” 

I responded: “Best advice I can give is just stay true to what you’ve been doing and don’t overthink things.” 

When Ed heard the Lions would likely rest star wide receiver Amon-Ra St. Brown, he decided to roll with the Bears one more time over the Rams. St. Brown ended up playing and totaled a team-high 11 catches for 139 yards in the upset victory. 

Keep in mind, Chicago trailed Detroit 16-0 in the fourth quarter and scored two touchdowns with two-point conversions to tie the game with 5:25 remaining. Watching how the Bears beat the Packers to advance in the playoffs, it would not have been surprising to see them score the game-winning touchdown and cover the spread. A Jared Goff interception with 2:23 left seemingly put Chicago in the perfect position. But it wasn’t to be.

Bears second-year quarterback Caleb Williams set an NFL record with six comeback wins in the final two minutes before the last two games of the regular season. However, much like Michael Jordan didn’t make all of his game-winning shot attempts for the Chicago Bulls during his Hall of Fame career, Williams proved to be mortal and fell short in those two losses to the Lions and 49ers when he was needed the most. For Ed, anyway.

Fading Bears Helps Others Finish Strong

On the flip side, another pair of our client entries Wink and Potato Kmish picked Detroit in Week 18 and went a combined 9-1 to earn $525,000 between them thanks to fourth and seventh-place finishes, respectively. The Lions came through for them in what was an otherwise forgettable season for the team from the Motor City. A loss would have cost them and others hundreds of thousands of dollars, so this was still a positive result for many.

When Ed had some time to reflect on his journey throughout the 2025 NFL season, he was grateful for the experience and decided to attend the check presentation ceremony last Friday at Circa along with Christopher Convery (Wink) and Jack Lenenberg (Potato Kmish). Ed also tied for 12^th place in the SuperContest, the original pick-five competition at the Westgate Las Vegas Resort & Casino, and he is one of the best clients we have. 

I asked Ed who he liked in the Green Bay-Chicago game, and he said the Packers. I told one of his friends the Bears owed him for disappointing him down the stretch. Fortunately, contest season was finally over, and another Chicago miracle did not make a difference.