Simmons, probably rap's greatest entrepreneur, lives in New York; schmoozes bankers, fashion designers, and record executives; and cuts deals with conglomerates such as Time Warner.
( ( ( ( ( Simmons , ) probably ) ( ( rap 's ) ( greatest entrepreneur ) ) ) , ) ( ( ( ( lives ( in ( ( ( ( New York ) ; ) ( ( ( ( ( ( schmoozes bankers ) , ) ( fashion designers ) ) , ) and ) ( record executives ) ) ) ; ) ) ) and ) ( ( cuts deals ) ( with ( conglomerates ( such ( as ( Time Warner ) ) ) ) ) ) ) . ) )
(ROOT (S (NP (NP (NNP Simmons)) (, ,) (ADVP (RB probably)) (NP (NP (NN rap) (POS 's)) (JJS greatest) (NN entrepreneur)) (, ,)) (VP (VP (VBZ lives) (PP (IN in) (NP (NP (NNP New) (NNP York)) (: ;) (NP (NP (JJ schmoozes) (NNS bankers)) (, ,) (NP (NN fashion) (NNS designers)) (, ,) (CC and) (NP (NN record) (NNS executives))) (: ;)))) (CC and) (VP (VBZ cuts) (NP (NNS deals)) (PP (IN with) (NP (NP (NNS conglomerates)) (PP (JJ such) (IN as) (NP (NNP Time) (NNP Warner))))))) (. .)))
Simmons is known for dating New York's most prominent fashion designers. 
( Simmons ( ( is ( known ( for ( ( dating ( New ( York 's ) ) ) ( most ( prominent ( fashion designers ) ) ) ) ) ) ) . ) )
(ROOT (S (NP (NNP Simmons)) (VP (VBZ is) (VP (VBN known) (PP (IN for) (NP (NP (NNP dating) (NNP New) (NNP York) (POS 's)) (JJS most) (JJ prominent) (NN fashion) (NNS designers))))) (. .)))