The attorneys at Criminal Appeals Advocates (CAA) often discuss the “federal writ” appeal option with the firm’s clients.  This option involves bringing a state court conviction into federal court to allow a federal judge to review the conviction. 

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Federal writs, also known as 2254 or 2255 motions, are exceptionally difficult to win, as they require proving that an inmate’s Constitutional rights were violated. Nonetheless, a small number of inmates do win their freedom through federal writs.

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This exclusive CAA analysis discusses some of the most defense-friendly federal judges, including further analysis. 

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Frederic Block

Senior U.S. District Judge, E.D. New York

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Judge Block has issued notable below-guideline sentences emphasizing fairness. In U.S. v. Nesbeth (2016), guidelines recommended 33–41 months in prison, but Judge Block gave probation instead. He wrote a 42-page opinion arguing that the severe collateral consequences of a felony conviction already provided sufficient punishment. This case is cited as an example of a judge prioritizing rehabilitation and proportionality over harsh incarceration. He was recently interviewed in Legal Talk Network in the episode “When should life sentences be overturned? Judge shares how he decides” (1/8/2025).

 

Jed S. Rakoff

Senior U.S. District Judge, S.D. New York

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Well-known for skepticism toward draconian sentences, especially in white-collar cases. In one fraud case (guidelines called for ~85 years), Judge Rakoff decried the guideline result as “an utter travesty of justice” and imposed a far lower term. He frequently speaks and writes about unjust sentencing and has diverged from guidelines to impose what he views as more just outcomes.

 

John C. Coughenour

U.S. District Judge, W.D. Washington

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Judge Coughenour is an outspoken critic of federal sentencing guidelines, often issuing below-guideline sentences. Coughenour’s sentences are only ~20% compliant with guideline ranges (meaning ~80% are below). In a terrorism case, he imposed 22 years (vs. a 65-years-to-life guideline) due to the defendant’s cooperation – prompting commentators to label him overly lenient (dubbed “the terrorists’ little helper” by one critic).

 

Tanya S. Chutkan

U.S. District Judge, District of Columbia (Washington DC)

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Judge Chutkan is a former public defender with a reputation for appreciating defendants’ rights. Described by a former Solicitor General as “a little bit of a defendant-friendly judge” who brings a “hearty appreciation for the rights of criminal defendants” to the bench[6]. (Notably, in Jan. 6 riot cases she has actually been tougher than peers, but her defense background suggests sympathy to due process.)

 

John J. McConnell Jr.

Chief U.S. District Judge, D. Rhode Island

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Under his court’s watch, Rhode Island’s federal district has had extraordinarily high rates of below-guideline sentences. U.S. Sentencing Commission data (FY2019) showed ~72% of defendants in D.R.I. got sentences below the guideline range (without government motions), the highest rate in the nation, earning it a label as “America’s most lenient federal court.” This reflects a pattern of judges (including McConnell) often imposing below-average punishments.

 

Analysis and Trends

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Several trends emerge from these examples. First, judges who are defense-friendly often have a philosophical opposition to rigid sentencing guidelines or mandatory minimums. Many of the judges above have publicly criticized the guidelines as too harsh or “overly punitive”, especially for non-violent and first-time offenders. For instance, Judge Coughenour and Judge Rakoff have explicitly argued that blindly following the guideline “score” can produce unjust outcomes, and they have acted on that belief by sentencing well below the guideline ranges in many cases. Similarly, Judge Block has used his discretion to temper what he viewed as excessive punishments.

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Another pattern is that some of these judges have professional backgrounds that attune them to defendants’ rights. Judge Chutkan’s years as a public defender, for example, contribute to her appreciation of due process and fairness for the accused. This doesn’t always mean they are lenient in every case – indeed, Chutkan has been tough in certain contexts (e.g. January 6 cases) – but it suggests they scrutinize the government’s position and ensure defendants get a fair shake. Likewise, judges like Helen Berrigan and Nancy Gertner (a retired D. Mass. judge and noted sentencing reform advocate) earned reputations for empathy toward defendants and skepticism of prosecution arguments, often being described as “liberal” or “lenient” in their approach (though such characterizations are sometimes controversial).

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It’s important to note that objective metrics for “leniency” can be hard to generalize. The U.S. Sentencing Commission does not publish rankings of individual judges by average sentence. However, data at the district level show some courts deviating from guidelines far more than others. The District of Rhode Island’s striking 72% below-guideline rate is a prime example – suggesting a local judicial culture more willing to give sentences below the guideline recommendations. In contrast, other districts (often in the South) stick to guidelines much more frequently (for instance, by comparison, some circuits in the South have guideline compliance rates well above 60%). These discrepancies hint that a handful of judges (or U.S. Attorneys’ charging practices) can dramatically influence how “defendant-friendly” a district is seen.

 

Thus, while comprehensive rankings are rare and often debated, there is evidence that certain judges stand out for sentencing below national norms or for siding with defendants on key issues. Many of these judges justify their leniency with principled reasoning: concern for rehabilitation, belief in second chances, or the view that mandatory laws are too sweeping. At the same time, labeling a judge “lenient” can be contentious – what defense attorneys praise as compassion, others (including prosecutors or pundits) may criticize as “soft”. Overall, the trend in the past 10–15 years has been a growing acknowledgment (even among many judges) that one-size-fits-all sentencing can lead to injustice. Thus, judges known for being favorable to defendants often play a key role in pushing back against the toughest edges of the system, though they remain constrained by laws and higher courts.

 

Learn More:

 

To hear more insights from the attorneys at Criminal Appeals Advocates you can visit the Knowledge Series at www.CriminalAppealsAdvocates.com/knowledge. Please note that the CAA attorneys are not available to offer free legal advice, as their time is dedicated to the law firm’s current clients. CAA can be reached at (267) 662-1671.