By Matt Dolloff, CBS Boston

BOSTON (CBS) — Frank Rybczyk made the trek from Middletown, Conn. to the heart of Boston on a cold, rainy Saturday in 1957. To escape the nasty Boston weather, he and a group of three friends had grabbed four tickets to the Celtics – who happened to be playing for the NBA championship. They beat the St. Louis Hawks to win the first of their would-be 17 championship banners.

It was a time where the Red Sox were by far the biggest ticket in town and the Celtics had yet to begin building their legacy as the NBA’s most prolific championship franchise. So Rybczyk and his pals were able to waltz into the Garden to catch the team’s first-ever NBA championship, fully unaware of the dynastic run that would follow.

It was far from the first time Rybczyk would experience such good fortune.

Rybczyk, who turns 77 on Jan. 24, rode his longtime fandom of professional football – and a remarkable run of good luck – to win the 2016 CBS Local Pro Football Challenge. He outlasted over 24,000 national entrants and beat out Boston’s own experts like Bob Socci, Dan Roche, Tony Massarotti, and several others. Entering on, Rybczyk won himself a $5,000 American Express Gift Card.

How did Rybczyk, who now resides in Montgomery, Ala., pull it off? While he repeatedly insisted that he simply “got lucky” – everyone needs some luck to win such a large contest – he mostly looked at who was under center.

“I primarily looked at quarterback matchups,” said Rybczyk, who has been following the NFL since the pre-Super Bowl days in the 1950s, before the Patriots even existed. “Obviously I like [Tom] Brady, I like Matt Ryan, I like [Matthew] Stafford, I like Derek Carr. … If they were playing, I picked them. That’s really the only thing I did.”

Considering that Brady put together one of the finest seasons of his career, Ryan may well be the NFL MVP, and both Carr and Stafford put together career-best seasons, that was certainly a sound strategy. It’s what Rybczyk rode all the way to victory.

Rybczyk mostly picked randomly for the first two-thirds of the NFL season. It wasn’t until Week 12 that he noticed he was at the top of the leaderboard.

“I thought a little more about my picks after that,” said Rybczyk, who clinched at least a tie in the Pro Football Challenge by the time Monday Night Football of Week 17 kicked off.

Besides being a “nice birthday present” for Rybczyk after the season ended in frustration for his beloved Red Sox, the Pro Football Challenge win was the culmination of a lifetime spent rooting for Boston teams and brushing up against its greatest legends.

Having served for 20 years in the Air Force, Rybczyk once lived and worked at a post office in Clearwater, Fla. It was there where he encountered Red Sox legend Ted Williams on several occasions, at one point chatting with him for about 15 minutes. As it would be for many Red Sox fans, meeting his idol was a once-in-a-lifetime moment he’ll never forget.

“He’s my John Wayne,” Rybczyk said of Teddy Ballgame. “The guy was a Marine pilot, a fisherman … and the greatest hitter who ever lived.

“That was my greatest sports thrill, to talk with Ted.” This coming from a man who witnessed Red, Russell and Cousy winning the Celtics their first championship.

As for his own athletic background, Rybczyk’s “claim to fame” was a spot on the roster for Middletown in the 1948 Little League World Series. Standing at 5-foot-5, Rybczyk was “very good at everything but not good enough,” yet certainly had the talent to make it into a Little League tournament that only contained six teams at the time.

Middletown was one-and-done in that tournament, but it was far from the end of the history Rybczyk would witness first-hand. Now a big winner in the Pro Football Challenge, Rybczyk is making plans for what to do with his winnings.

The Patriots head to New Orleans to play the Saints in 2017 and the Superdome is about as far from Montgomery as Boston is from New York City, so Rybczyk and his wife plan to make the drive to see the Pats play in person. He also plans to attend every game of the Red Sox’ mid-July series against the Yankees at Fenway Park.

Considering his recent run of good fortune, perhaps there’s a good chance the Patriots and Red Sox deliver him some wins in person. It certainly wouldn’t be the first time he got to see his home team deliver.

Rybczyk has been picking football games for decades but never had the run like he did in 2016. For now, he’s doing his best to appreciate the good fortune that’s hit him in recent months.

“I’ve been doing it for years, and I’ve never been this lucky.”

Matt Dolloff is a writer for Any opinions expressed do not necessarily reflect that of CBS or 98.5 The Sports Hub. Have a news tip or comment for Matt? Follow him on Twitter @mattdolloff and email him at


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