Nyorai kuenderera mberi kweiyi ndima - Eastwood akanyorwa muChishanu Round, 91st yakazara neToronto Maple Leafs mu1987 NHL Entry Draft
. Akabva atamba mwaka mina neWestern Michigan University yeCCHA. Akatamba mitambo 164 yeWestern Michigan, achihwina zvibodzwa 69 uye achiwedzera makumi masere ekubatsira kwemapoinzi zana nemakumi mana nemapfumbamwe. Mwaka wake wakaisvonaka wakanga uri wokupedzisira apo akanga ane 29 vavariro uye 32 anobatsira mumitambo 42. Muna 1991, Eastwood akaita nhangemutange yepro hockey. Haana kuva NHL nguva dzose kunyange kusvikira makore maviri gare gare.