Historical clue formulations

• Massive amounts of winnings, so to speak — 2026-01-28
• Schleps — 2025-03-18
• Transports — 2020-06-05
• Lugs — 2020-04-26
• Fisherman's takes — 2016-05-17
• Trucks, maybe — 2014-12-21
• Does semi-related work? — 2010-06-26
• Carries — 1998-11-24
• Moves by rail — 1994-09-11