Lou Williams and Jamal Crawford are tied for the most career Sixth Man of the Year awards, with 3.

who has won the most sixth man of the year awards

NAME	SMOY	GP	MPG	PPG	RPG	APG	SPG	BPG	TPG	FGM	FGA	FG%	3PM	3PA	3P%	FTM	FTA	FT%	MIN	PTS	REB	AST	STL	BLK	TOV	PF	+/-
Lou Williams	3	1,123	24.1	13.9	2.2	3.4	0.8	0.2	1.7	4.5	10.7	41.9	1.3	3.7	35.1	3.6	4.3	84.2	27,104	15,593	2,484	3,789	952	192	1,896	1,439	+575
Jamal Crawford	3	1,327	29.4	14.6	2.2	3.4	0.9	0.2	1.9	5.1	12.4	41.0	1.7	4.8	34.8	2.8	3.2	86.2	38,994	19,419	2,948	4,541	1,179	271	2,476	2,008	-1250
Detlef Schrempf	2	1,136	29.6	13.9	6.2	3.4	0.8	0.3	2.0	4.8	9.7	49.1	0.4	1.1	38.4	3.9	4.9	80.3	33,597	15,761	7,023	3,833	856	312	2,268	3,360	+1274
Ricky Pierce	2	969	24.4	14.9	2.4	1.9	0.8	0.2	1.5	5.6	11.3	49.3	0.3	0.9	32.2	3.5	4.0	87.5	23,665	14,467	2,296	1,826	768	147	1,453	2,213	-123
Kevin McHale	2	971	31.0	17.9	7.3	1.7	0.4	1.7	1.9	7.0	12.7	55.4	0.0	0.2	26.1	3.7	4.7	79.8	30,118	17,335	7,122	1,670	344	1,690	1,893	2,758
Tyler Herro	1	284	31.8	18.1	4.9	3.6	0.7	0.2	2.2	6.7	15.1	44.0	2.6	6.7	38.5	2.2	2.6	87.2	9,038	5,147	1,403	1,036	194	53	613	406	+333
Malcolm Brogdon	1	439	29.4	15.4	4.2	4.7	0.8	0.2	1.7	5.7	12.3	46.4	1.7	4.3	39.1	2.4	2.7	87.3	12,916	6,772	1,826	2,058	357	103	751	816	+611
Montrezl Harrell	1	515	20.5	12.1	5.0	1.3	0.5	0.8	1.1	4.9	7.9	61.9	0.0	0.2	10.8	2.3	3.5	66.4	10,544	6,220	2,588	675	269	404	550	1,058	+652
Jordan Clarkson	1	716	27.7	16.0	3.4	2.9	0.8	0.1	1.9	6.0	13.7	43.8	1.8	5.5	33.5	2.1	2.6	83.2	19,861	11,429	2,405	2,073	583	107	1,330	1,214	-1150
James Harden	1	1,072	34.7	24.1	5.6	7.1	1.5	0.6	3.7	7.1	16.2	44.1	2.7	7.5	36.4	7.1	8.3	86.1	37,222	25,885	6,017	7,629	1,597	600	3,919	2,695	+4263
Eric Gordon	1	886	31.7	15.7	2.3	2.8	0.8	0.4	1.9	5.3	12.4	43.0	2.3	6.2	37.1	2.7	3.3	81.1	28,115	13,868	2,067	2,443	750	313	1,648	1,578	-48
Ben Gordon	1	744	27.4	14.9	2.5	2.5	0.7	0.2	2.1	5.3	12.2	43.2	1.6	3.9	40.1	2.8	3.2	85.7	20,366	11,084	1,851	1,868	508	114	1,551	1,720	-678
JR Smith	1	977	26.9	12.4	3.1	2.1	1.0	0.2	1.3	4.5	10.7	41.9	2.0	5.3	37.3	1.5	2.0	73.3	26,275	12,148	3,073	2,077	974	204	1,315	2,191	+1427
Leandro Barbosa	1	850	21.6	10.6	2.0	2.1	0.8	0.1	1.2	4.0	8.7	45.9	1.2	3.0	38.7	1.5	1.8	82.1	18,386	9,035	1,720	1,775	693	121	1,061	1,651	+461
Manu Ginobili	1	1,057	25.4	13.3	3.5	3.8	1.3	0.3	2.0	4.3	9.7	44.7	1.4	3.8	36.9	3.2	3.9	82.7	26,859	14,043	3,697	4,001	1,392	319	2,116	2,212	+5468
Mike Miller	1	1,032	26.9	10.6	4.2	2.6	0.6	0.2	1.5	3.9	8.5	45.9	1.5	3.8	40.7	1.3	1.7	76.9	27,812	10,973	4,376	2,666	573	229	1,561	2,043	-168
Lamar Odom	1	961	33.4	13.3	8.4	3.7	0.9	0.9	2.3	5.0	10.8	46.3	0.7	2.2	31.2	2.6	3.7	69.3	32,131	12,781	8,059	3,554	848	892	2,253	2,916	+1556
Jason Terry	1	1,410	29.8	13.4	2.3	3.8	1.1	0.2	1.7	4.9	11.1	44.4	1.6	4.3	38.0	2.0	2.3	84.5	42,034	18,881	3,274	5,415	1,603	275	2,415	2,577	+1718
Antawn Jamison	1	1,083	34.8	18.5	7.5	1.6	1.0	0.4	1.6	7.1	15.7	45.1	1.1	3.1	34.6	3.3	4.5	72.4	37,638	20,042	8,157	1,761	1,048	421	1,714	2,580	-1424
Bobby Jackson	1	755	22.2	9.7	3.1	2.6	0.9	0.1	1.3	3.6	8.7	41.7	0.9	2.6	35.4	1.5	1.9	79.3	16,790	7,344	2,347	1,945	704	68	1,014	1,372	+390
Corliss Williamson	1	822	22.8	11.1	3.9	1.2	0.6	0.3	1.6	4.4	8.9	49.0	0.0	0.1	13.6	2.4	3.3	71.4	18,749	9,147	3,183	972	462	261	1,316	2,250	+294
Darrell Armstrong	1	840	23.7	9.2	2.7	4.0	1.3	0.1	1.9	3.2	7.7	40.9	1.1	3.3	33.4	1.7	2.0	87.1	19,915	7,712	2,269	3,394	1,133	98	1,556	1,398	+554
Aaron McKie	1	793	24.2	7.4	3.3	2.7	1.2	0.2	1.3	2.9	6.5	43.8	0.5	1.4	35.0	1.2	1.5	77.9	19,156	5,871	2,587	2,126	912	164	1,059	1,588	+740
Toni Kukoc	1	846	26.3	11.6	4.2	3.7	1.0	0.3	1.8	4.3	9.6	44.7	0.9	2.6	33.5	2.1	2.9	72.9	22,212	9,810	3,555	3,119	817	290	1,544	1,465	+1193
Rodney Rogers	1	866	25.3	10.9	4.5	2.0	1.0	0.5	1.9	4.2	9.2	45.1	0.8	2.3	34.7	1.8	2.6	69.0	21,873	9,468	3,881	1,722	868	451	1,631	2,678	-251