Yoshiki was hard up for money and asked Goro to lend him twenty thousand yen.

Literal

Yoshiki [topic-は] money [in-に] troubled Goro [to-に] 20,000-yen lend [please-てくれと] asked.

~てくれと頼む is the casual quotative version of ~てくれるように頼む — both mean 'ask someone to do X for me as a favor,' but here と marks the quotative content of the request more directly. 金に困る ('to be hard up for money') is a set phrase with に marking the domain of trouble. Names: 良樹 (Yoshiki) and 五郎 (Goro).