How to say he had a hard time to disengage himself from the gang. in Japanese

1)彼(kare) (ok) that , or something understood without naming it directly)/that person/over there/hey/eh?/thatは(ha) (int) indicating a subject/yes/indeed/well/ha!/what?/huh?/sighそのその(sono) (n,n-suf) that/garden/orchard/park/plantation/place/location仲間仲間(nakama) (n) company/fellow/colleague/associate/comrade/mate/group/circle of friends/partnerからから(kara) (prt) from/since/from/because/out of/through/after/since自由自由(jiyuu) (exp,adj-na,n) freedom/liberty/as it pleases youになるになる(ninaru) (suf) becomes/will become/turns out/grammatical form creating an honorific verbal expressionのにのに(noni) (prt) although/when/and yet/despite this/in spite of/even though/but even so/but even then/however/nevertheless/for all that/notwithstanding that/while/if only/i wish/i tell you/you should do/in order to苦労苦労(kurou) (adj-na,n,vs) troubles/hardshipsしたした(shita) (n) did/a past form of the previous verb/tongue/tongue-like object/clapper/talon。(。) Japanese period "."    
kareha sono nakama kara jiyuu ninarunoni kurou shita 。
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