In the play In New England Winter, the second of Ed Bullins's Twentieth Century Cycle, Cliff Dawson returns from In the Wine Time. Here, he is older and more subdued; though still stung by a failed marriage, he seeks to shore up ties with his estranged half-brother Steve, who caused the divorce. It is Steve's character, however, that occupies much of the play's emotional energy; his meticulousness in plotting a robbery that he, Cliff, and two cohorts are about to commit, is entirely directed toward obtaining “traveling money” for a return to New England in winter and for Liz, the woman he had long ago left there.
The play's seven sections are divided more or less evenly between a present of 1960, in which the four men are planning the robbery, and flashbacks to 1955, when Liz, Steve, and their alcoholic friends while away the time in New England. Liz, recovering from a severe breakdown, articulates a daydream about the love that she and Steve share and the children it will produce, but her fears that Steve's AWOL status from the navy may suddenly mean their separation suggest a relapse. Additionally, a drunken misunderstanding that finds Steve sleeping innocently in the arms of Liz's sister Carrie causes Liz's fears to become reality as Oscar, Carrie's angered husband, threatens to kill Steve, and Crook, another drinking partner who has been waiting for an opportunity to steal Liz, betrays Steve to the authorities.
Though Steve manages to escape, his efforts in 1960 to get back to Liz are hampered by an oppressive summer heat, the difficulty of planning the robbery, and the differences between himself and Cliff. Principally at issue is Steve's affair with Cliff's wife Lou and the child they produced while Cliff was in jail for murder; one of the cohorts, Bummie, knew of the liaison. But Cliff's prior knowledge of this is a measure of Cliff's magnanimity unknown to Steve, who kills Bummie before he can be betrayed. The brothers reconcile, and Steve resumes his plan to return to New England, but the audience's poignant understanding is that a confused and frightened Liz, after Steve's departure in 1955, had already succumbed to the charms of the serpentine Crook.
Warren R. True notes that because the play's tension seems to emanate entirely from Steve, Cliff, and the two cohorts, Steve's stabbing of Bummie does not appear to be a logical climax. That the tautness among these four grows steadily throughout the play, however, renders the crisis static and unobtrusive, and in this light the play's structure invites comparison to Chekhovian dramaturgy. Genevieve Fabre, however, finds that the folkloric aspects of Bullins's earlier plays are not in evidence here. The symbolism of snow seems gratuitous, and the simple episodic construction forces the play to depend on Bullins's preceding plays for its vigor. Additionally (and unlike Chekhov), this play, like the rest of Bullins's dramas, depends not on tragedy but rather on melodrama, an element that appears often in African American theater.