For several years he traveled in a circuit of federal courthouses in Montgomery, Mobile, Selma, Dothan and Opelika.

During the Civil Rights Era, Judge Pittman was assigned two complex cases brought by the NAACP involving at-large offices in Mobile County, Alabama.

Former Chief Judge Thomas had handled the Birdie Mae Davis school desegregation case for decades, which ultimately reached the United States Supreme Court twice, but would be overshadowed by school desegregation cases from Virginia and North Carolina.

A similar case, also discussed below, involved the at-large election of the school board, and the lead plaintiff was Lila Brown.

At the heart of both cases was the at-large election system begun following the 1911 revision of Alabama's constitution; no African Americans had thereafter won any county-wide office.

[4] The Bolden case went to trial on July 12, 1976; and on October 21, 1976, Judge Pittman issued a decision for the plaintiffs[5] which led to considerable controversy.

[6][7] Ultimately, the United States Supreme Court granted certiorari and in Mobile v. Bolden reversed the appellate judgment and vacated Judge Pittman's decision.

Meanwhile a "smoking gun" letter was discovered and admitted into evidence—written by Mobile lawyer and Congressman Frederick G. Bromberg to the Alabama legislature in 1909, it clearly indicated the purpose of the at-large system was to prevent blacks from holding office.

[10] On January 31, 1983, rather than appeal, all parties agreed to a settlement whereby the next election for city office would be based on districts rather than at-large.

Thus it came more than a decade since the Birdie Mae Davis school desegregation case had begun, and after the November 1974 elections replaced long-time school board members Charles McNeil and William Crane with young local attorney Dan Alexander (who would become the school board's dominant force for decades, but after declining to run for election after resolution of the Brown legal case, would be convicted for extorting kickbacks from local architects as Mobile's schools finally began addressing infrastructure deficits in 1977) and Ruth Drago (a retired teacher and former president of the Mobile County Education Association and Alabama Education Association).

Retired air force officer Norman Cox and local dentist and NAACP president Robert Gilliard had been elected as the school board's first black members, each from a majority-black district.

However, Judge Pittman's orders from the Bolden and Brown cases proved controversial, and appeared to require a special school board election in 1983.

[18] Judge Pittman remained married to his first wife, Floy Lassater, for 56 years, even becoming her main caregiver when she was stricken with Alzheimer's disease.