In 2005, the Pirates announced the Matt Lawton for Jody Gerut deal right at the deadline -- around 4pm on Sunday, July 31. Bones was on it.
In 2004, the Pirates announced the long-rumored Ty Wigginton, Matt Peterson, and Jose Bautista for Kris Benson deal around 5pm on Friday, July 30. Bones was on it.
In 2003, the Pirates announced a bunch of trades through July, and they did a deal after the deadline, too.
July 8, 2003: Traded John Wasdin to the Toronto Blue Jays. Received Rich Thompson.
July 21, 2003: Traded Mike Williams and cash to the Philadelphia Phillies. Received Frank Brooks.
July 22, 2003: Traded Mike Gonzalez and Scott Sauerbeck to the Boston Red Sox. Received Brandon Lyon and Anastacio Martinez.
July 23, 2003: Traded Aramis Ramirez, Kenny Lofton, and cash to the Chicago Cubs. Received a player to be named later, Jose Hernandez, and Matt Bruback (minors). The Chicago Cubs sent Bobby Hill (August 15, 2003) to the Pittsburgh Pirates to complete the trade.
July 31, 2003: Traded Brandon Lyon, Jeff Suppan, and Anastacio Martinez to the Boston Red Sox. Received Mike Gonzalez, Freddy Sanchez, and cash.
August 17, 2003: Traded Randall Simon to the Chicago Cubs. Received Ray Sadler.
I think we all remember that month as the start of Littlefield's tenure. Thank you Baseball Reference.
I have a supply of candles to keep burning on the drinking table through Monday. The Pirates play the Giants at home on Sunday afternoon. There is no game on Monday and a night game at home on Tuesday. It's my guess that the Pirates make more or less the kind of trades we expect them to make on Monday afternoon.