Dhameystir weedha soo socota: Kadib 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 hogaaminayo 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 ay ka soo horjeedeen Franchise kaas oo Henry uu la lahaa ka qaybqaadashada kahor ballaarinta, Rockies, iyo
Horyaalka Adduunka ee 2018 ee ay la ciyaareen 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.