No doubt that’s what Freddie meant, but it’s not the precise definition of "chalk." Rather, it’s a term generally applied to sports betting that means the favored side. It comes from the days before electronic betting boards, when sports books used blackboards to display the game lines.
The favorite is traditionally shown with the pointspread preceded by a minus ("-") sign, as in,
Kansas -7 USC
Thus, the favorite was the team that had the chalk mark (i.e., the pointspread) next to it.
Note that the line can also appear without the minus sign:
Kansas 7 USC
It’s understood that the team followed by the number is the favorite.
So you might hear that someone likes to "bet chalk" or is a "chalk player," meaning he usually bets favorites. Of course, the term has morphed to apply to more than betting and is used, as Freddie Coleman did, to identify a favorite, or favorites, in a contest ("Pittsburgh and Connecticut are the chalk").
Interestingly, on the day we received this question, we saw a newspaper headline that read, "Obama Goes with Chalk," after the president chose Louisville, North Carolina, Pittsburgh, and Memphis, all high seeds, to make it to the March Madness Final Four.
Finally, in our favorite usage of the term, we heard a bettor referred to as "ChalkBoy SquarePants" -- a play on the cartoon SpongeBob SquarePants, meaning the player was a square (loser) who always bet favorites.
