Darling's Trading In His Chevy For a Cadillac-ac-ac-ac-ac

If baseball announcers are to be believed, Cadillacs are best enjoyed at a modest cruising speed.
After all, "Cadillacing" after a batted ball means taking your time in getting to it.

"A simple ground ball up the middle in almost game, Heyward kind of Cadillacs in and gets that ball," said Ron Darling during Dodgers-Braves last week. "But he cannot with Puig running."

Darling has long had a thing for Cadillacs. As a minor leaguer back in 1982, he said in Newsday about making the Big Show:

"The money is secondary, really. I'm a pretty frugal guy, although in New York my frugalities might include a Cadillac."

During day games at CitiField, Darling will often share the booth with Ralph Kiner, who had a little something to say about Cadillacs during his illustrious playing career.

"Home run hitters drive Cadillacs," Kiner famously said, "and singles hitters drive Fords."

Funny, I was half tuning in last night to Sox-Rays, and another announcer on TBS--not Darling--referred to a player "Cadillacing" in for a fly ball. 

Did he get it from Ron? Or is it a real baseball term?

In fact, "Cadillacing" been around for some time. The radio program A Way With Words cites the Seattle Times waaayyy back in 1989:

"He moved to his right to catch a fly out, but Greg Gagne surprisingly tagged from first base and reached second when Griffey’s threw was too soft and wide. “I don’t like him ‘Cadillacing’ like that,” he said. 

The University of Oregon has the word in its online slang dictionary, and defines "Cadillacing" thusly:

To run in an unhurried, showy way; generally, to perform or operate lackadaisically, carelessly, or without worry  

Finally, we turn to hip-hop for a bit of clarity. The emcee Paul Wall rapped this in 2008:

These boys lazy Cadillac'ing, while I'm greenback stacking

So Cadillacing has been around for some time, yet seems to be the darling of the baseball announcer set these days.