|The “Three Amigos” is a common characterization of relations among the North American countries, particularly since 1 January 1994 when the North American Free Trade Agreement (“NAFTA”) entered into force, superseding a deal between two buddies, Canada and the United States, the Canada-United States Free Trade Agreement (“CUSFTA”), that had been in effect since 1 January 1989. For nearly all of the almost quarter century of NAFTA history, America, Canada, and Mexico enjoyed a stable and growing trade relationship, based on a healthy friendship.Then Donald J. Trump was inaugurated on 20 January 2017, having won the Presidency in part with anti-NAFTA, and particularly anti-Mexico, vitriol. No longer did the common characterization of “Three Amigos” seem apt. As the Trump Administration NAFTA renegotiation goals emerged, that portrayal seemed quite misleading. Instead, Shakespeare’s great tragedy, Othello, provides characters to whom the three NAFTA Parties may be analogized, albeit loosely.The argument of this Article is that on the stage of NAFTA renegotiations, the Trump Administration has changed the script, casting America as Iago, and consequently putting Mexico in the role of Cassio, and Canada as Desdemona.The transformation from Three Amigos to tragic figures is neither complete nor irreversible. But, it is grounded in hard-core, technical trade details, with America at the center of the plot of NAFTA renegotiations, as is Iago in Othello. There would have been no such renegotiations but for the scheming of candidate and now President Trump. He stirred the pot, as it were, in what was an otherwise undramatic, well-functioning, though not problem-free, relationship with Mexico and Canada.Enmity, concealment, improvisation, omission, and corruption are the five hallmarks of Iago that render him infamous among Shakespeare’s characters. Iago hates Othello. Iago conceals the truth from all those around him. Iago is a master at improvisation to further his wicked plans. Iago omits material facts, thereby leading others astray. Finally, Iago corrupts the relationships of those who share the closest bonds.Each hallmark is apparent in the Trump Administration’s NAFTA renegotiating strategy. Trade negotiations always have had a theatrical character to them, characterized by: late-night talks on acrimonious issues among commercial allies and adversaries that thrust deadlines and ultimatums on each other; trade-offs among sectoral interests that sometimes at best are cynical and at worst irrational; and raw power asserted by the economically strong over the relatively impoverished. But, the drama this Administration has brought to NAFTA renegotiations is unprecedented for America’s global theater company (otherwise known as the United States Trade Representative (“USTR”)) and risks an unparalleled tragedy.First, enmity towards Mexico’s bilateral trade surplus with America motivates the Trump Administration’s NAFTA renegotiation strategy. Second, that motivation conceals a corporatist agenda favoring certain powerful American business sectors, such as winter vegetable producers and e-commerce companies—an agenda the Trump Administration is advancing through secret talks with Mexico and Canada. Third, the very engagement in NAFTA renegotiations is an act of improvisation, tossing out most of the clear, final script from the Trans-Pacific Partnership (“TPP”), and concocting a new agenda for discussions. Fourth, the Trump Administration’s NAFTA renegotiation strategy omits serious help for labor interests, an irony when juxtaposed with pledges Mr. Trump made both before and after entering the Oval Office. Fifth, the effect of renegotiations, at least thus far, has been to corrupt the relationships between America and Mexico, and America and Canada.Again, by way of loose analogy, ever since Mexico committed itself to trade liberalization and economic reform in the mid-1980s, evidenced by its signing NAFTA on 17 December 1992,5 it has been a loyal partner of the United States. Loyalty, of course, is a defining virtue of Cassio, the lieutenant to Othello. Canada has supported warm trade relations with America since the 1989 CUSFTA, and indeed since the 1965 pact creating a free trade area in autos and auto parts. Despite disputes with America over softwood lumber and dairy products, Canada’s support for free trade was staunch, redolent of that of Desdemona for Othello himself. The Trump Administration has poisoned the relationship between America and Mexico, and America and Canada, as did Iago with respect to Cassio and Othello, and with respect to Desdemona and Othello.