Green’s Dictionary of Slang

1. to contest.

1917

Van Loan ‘Sanguinary Jeremiah’ in Old Man Curry 131: A day when all the burglars at the track will be levelling for the get-away money.

2. to be honest.

1917		Van Loan ‘Levelling with Elisha’ in Old Man Curry 28: Next Tuesday the Engle bunch will be levelling with Elisha.
1931		D. Runyon ‘Tobias the Terrible’ in Runyon on Broadway (1954) 106: I am now convinced that the guy is levelling with his tears.
1948		(con. 1944) N. Mailer Naked and Dead 617: You’re levelin’ with me, mister.
1957		H. Simmons Corner Boy 199: If you’re smart you’ll level with me.
1969		‘Iceberg Slim’ Pimp 179: I had to find out if she would level with me all the way.
1976		P. Theroux Family Arsenal 32: You levelled with me, Weech – about all those stolen goods – so I’m levelling with you.
1986		F. Taylor Auf Wiedersehen Pet Two 82: Sorry, Den. I should have levelled with you.
1991		(con. 1920s) O.D. Brooks Legs 144: The first thing you do is put the make on them, and if the figures are okay, level with them.
2000		F.X. Toole Rope Burns 23: How much you gettin? Level with me.

3. to admit, to confess.

1959		E. De Roo Young Wolves 132: I’m gonna level with Cliff.
1965		J. Thompson Texas by the Tail (1994) 87: He should have leveled with Red when Teddy first reappeared in his life.
1975		L. Rosten Dear ‘Herm’ 153: My problem is – Leo, do I level with Flo?
2000		N. Barlay Crumple Zone 169: Waiting for his sister to show, to explain things, to level with her, to put things back on track.