For many reasons, it’s good to be New England Patriots quarterback Tom Brady in Boston. However, in light of two recent Massachusetts trial court decisions, it may have been good for him that he was not in court in Boston over the summer when challenging the NFL’s adverse arbitration ruling. Over the space of two weeks in late November and early December, the Massachusetts Superior Court showed a markedly, if not surprising, pro-arbitration bent, as it upheld a party’s right to enforce an agreement to arbitrate, even after eight months of litigation in court, and upheld an arbitral award that applied out-of-state law in conferring multiple damages against a respondent despite a choice-of-law clause in the agreement mandating Massachusetts law. Either decision taken individually would be indicative of significant judicial deference to arbitration and arbitral awards. Together, they show the challenges that parties may face when attempting to avoid both an arbitration clause and/or a highly adverse, perhaps even peculiar, result.