Craig Sager’s extravagant attire, low-key cool and abundant humanity will always be most closely associated with the NBA. Yet Sager, who died Thursday at 65 after battling a rare form of cancer for more than two years, left a significant imprint on baseball in a broadcasting career that spanned more than four decades.

And perhaps most notably, his lifetime love of the Chicago Cubs ended in the best possible manner – with a championship and a winning wager.

The Cubs’ 108-year title drought ended in November with their seven-game World Series conquest of the Cleveland Indians. And Sager pocketed $4,000 from an annual tradition that finally paid off – wagering $1,000 on the Cubs to win the World Series.

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Sager laid out his reasoning for the wager – which he made 35 consecutive years, the first 34 in futile fashion – in his book, Living Out Loud, released earlier this year.

When Turner Sports acquired rights to a portion of Major League Baseball’s national TV rights in 2007, Sager had long established his chops as an NBA man. Yet, he folded seamlessly into TBS and TNT’s postseason coverage, even if his sartorial splendor looked slightly misplaced amid streams of tobacco juice outside a dugout rather than courtside in an NBA arena.

It was a somewhat appropriate turn, given that Sager’s face first was seen nationally on a diamond – when as a cub reporter for a Florida radio station, he boldly approached Hank Aaron at home plate after Aaron’s record-breaking 715th home run in Atlanta in 1974.

“I’d be shot,” Sager told Yahoo Sports in 2014 when asked what would happen if he tried a similar gambit in today’s climate.

Sager filled his MLB sideline role for Turner until 2013; most of his time and energy since was devoted to battling cancer.

On June 1, Sager fulfilled another dream when he was tapped to sing Take Me Out to the Ballgame at Wrigley Field before a game against the Los Angeles Dodgers.

He posed for pregame photos with several Cubs, including manager Joe Maddon, and getting loose in the batting cage for his first pitch.

He finally unleashed a strike from the mound to first baseman Anthony Rizzo, who himself battled cancer.

A few innings later, he fulfilled his singing duty with aplomb, finishing with a flourish by taking a fresh Cubs hat and flinging it to the crowd below.

Gallery: Craig Sager through the years