Waxad ku qortaa sii wadida faqradan - Ka dib iibintiisii Marlins, Henry wuxuu hogaamiyay iibinta Boston Red Sox oo ay la wadaageen Tom Werner iyo Shirkadda New York Times oo ka timid Yawkey Trust oo uu hogaamiyo John Harrington. Henry, oo ah milkiilaha ugu weyn iyo Werner, oo ah guddoomiyaha, waxay soo ururiyeen kooxda xafiiska hore oo uu hogaaminayo Larry Lucchino oo ujeedadiisu tahay "in la jebiyo habaarka Bambino". Waxa kale oo uu shaqaaleysiiyey Bill James oo ah hormuudka baseball sabermetrics, oo shaqadiisu si ballaaran loo yaqaanay ka dib markii la daabacay "Moneyball" 2003. Henry wuxuu dhammaystiray hadafkiisii horyaalnimada ee 2004 World Series, oo ka dhan ah ciyaartoygii uu jeclaa ee Cardinals, wuxuuna mar kale ka adkaaday Cardinals sanadkii 2013. Kooxda ayaa sidoo kale ku guuleysatay 2007 World Series oo ka soo horjeeday xayeysiis uu Henry la lahaa ka qaybgalka ka hor ballaarinta, Rockies, iyo 2018 World Series
waxay ka soo horjeedaan kooxda Dodgers. Henry waxa kale oo uu mas'uul ka yahay badbaadinta Fenway Park ee kubbada burburka. Milkiilayaashii hore ee Red Sox waxay qorsheynayeen inay dhisaan Fenway Park cusub oo ku xiga, laakiin Henry wuxuu doortay inuu sii wado oo uu dayactiro (oo ay ku jiraan kuraasta cusub ee Green Monster) Fenway Park ee hadda jira, kaas oo u dabaaldegay sannad-guuradii 100-aad ee 2012.