Mid-Level Associate — Complex Commercial Litigation

Winston & Strawn LLP — Mid-Level Associate, Complex Commercial Litigation (Chicago)

Location: Chicago, IL (Onsite)
Compensation: $260,000 – $365,000 (Cravath Scale, 3rd–5th Year) + discretionary bonus
Bar Admission: Illinois State Bar (required)

About Winston & Strawn LLP

Founded in 1853, Winston & Strawn is one of the nation's preeminent law firms and one of the oldest in Chicago. With 975+ attorneys across 16 offices spanning North America, South America, Asia, and Europe, the firm serves as a trusted adviser to clients across virtually every industry. Winston & Strawn's Chicago lawyers represent 90 Fortune 500 companies and are recognized in all major legal directories.

The firm's Litigation Department is ranked Tier 1 by Best Law Firms® and is recognized by Chambers USA for its distinguished commercial expertise. The complex commercial litigation practice is co-chaired by Samantha Lerner and features a deep bench of nationally recognized trial lawyers, including co-executive chairman Dan Webb, widely regarded as one of the nation's top trial lawyers.

The Chicago office is home to 290+ lawyers across 20+ practice areas, and is known for its collegial, high-performance culture. The firm dedicated over 19,000 hours to pro bono work in 2024. In 2026, Winston & Strawn is merging with UK-based Taylor Wessing to form Winston Taylor, significantly expanding its transatlantic capabilities.

The Opportunity

Winston & Strawn's Chicago office is seeking a dedicated and experienced mid-level associate to join its Complex Commercial Litigation group. This is a high-visibility role within one of the most active and respected litigation practices in the country, offering the opportunity to work on high-stakes matters alongside nationally recognized partners in both Illinois State and Federal courts.

Key Responsibilities

• Manage and coordinate complex commercial litigation matters through all phases, including pleadings, motions, discovery, expert development, and trial
• Take and defend depositions in high-stakes, multi-party cases
• Draft, file, and argue motions in Illinois State and Federal courts
• Manage all aspects of discovery in large, document-intensive cases, including e-discovery strategy and execution
• Conduct legal research and develop case strategy in collaboration with senior partners
• Engage directly with clients on case status, strategy, and risk assessment
• Prepare witnesses and trial materials for bench and jury trials

Required Qualifications

• J.D. from a top-tier law school with excellent academic credentials
• At least 3 years of broad-based general litigation experience at a top-tier law firm, or equivalent experience as a Federal Court judicial clerk
• Admitted to the Illinois State Bar (required)
• Demonstrated experience managing discovery in large, high-stakes commercial cases
• Proven track record taking and defending depositions
• Strong skills in drafting and arguing motions before state and federal courts
• Exceptional writing, research, and analytical capabilities
• Strong organizational skills and ability to manage multiple workstreams simultaneously

Ideal Candidate Attributes

• Experience in class action, antitrust, product liability, or securities litigation
• Federal court clerkship experience
• Trial preparation or trial experience
• Strong client-facing communication skills
• Interest in business development and long-term career growth within a leading global firm

Compensation (Cravath Scale)

• 3rd Year: $260,000 base + $57,500 year-end bonus
• 4th Year: $310,000 base + $75,000 year-end bonus
• 5th Year: $365,000 base + $90,000 year-end bonus

Total compensation includes comprehensive benefits (health, dental, vision, 401k), discretionary performance bonus, generous PTO, and bar dues/CLE reimbursement.

Why Winston & Strawn

• 170+ year legacy as one of America's most prestigious law firms
• Tier 1-ranked litigation practice with nationally recognized trial lawyers
• Collegial, collaborative culture with genuine investment in associate development
• Direct exposure to high-stakes, complex matters with early responsibility
• Fortune 500 client base across virtually every industry
• Expanding global platform through the upcoming Winston Taylor merger

Website: https://www.winston.com