Javier Vazquez and Boone Logan were traded together twice, a year apart. The first time from the White Sox to the Braves and the second time from the Braves to the Yankees.

As a Pirates fan, I immediately had a recollection of a trade with the Red Sox last decade, involving Freddy Sanchez. Eventually I ended up on Brandon Lyon’s B-R page, which probably best illustrates: – July 22, 2003: Traded by the Boston Red Sox with Anastacio Martinez to the Pittsburgh Pirates for Mike Gonzalez and Scott Sauerbeck. – July 31, 2003: Traded by the Pittsburgh Pirates with Anastacio Martinez and Jeff Suppan to the Boston Red Sox for Mike Gonzalez, Freddy Sanchez and cash. Probably not quite in the spirit of the post, since these two trades were obviously related,… Read more »

Tom Morgan and Mickey McDermott were traded from the Yankees to the A’s on 2/19/57 and from the A’s to the Tigers on 11/20/57. There were other players involved in both trades.

If a guy is on both ends of a trade, i.e., traded for himself, does that count?

Dave Magadan and Jeff Darwin were traded for each other twice in less than 5 months.

http://www.baseball-reference.com/players/m/magadda01.shtml
June 27, 1993: Traded by the Florida Marlins to the Seattle Mariners for Henry Cotto and Jeff Darwin.
November 9, 1993: Traded by the Seattle Mariners to the Florida Marlins for Jeff Darwin and cash.

Not exactly what Andy’s looking for, but Brad Ausmus was involved on both sides of a trade involving Doug Brocail. From Detroit to Houston FOR Brocail in 1996, then four years later, again from Detroit to Houston this time WITH Brocail…

I thought for sure some of those classic mid 90’s “swap meet” trades involving the Padres, Astros and Tigers would net a pair of players who were traded for each other twice, but the above was the closest I could find…

I can’t prove it using the B-Ref Transaction pages, but I’m pretty sure outfielder John-Ford Griffin and pitcher Jason Arnold were traded together from the Yankees to the A’s in mid-2002, and then traded together again from the A’s to the Blue Jays during the following offseason.

I imagine looking at the old KC/New York shuttle from the 1950’s would yield more than one example of this.

Dave LaPoint and David Green were twice traded together.

• December 12, 1980: Dave LaPoint traded by the Milwaukee Brewers with David Green, Sixto Lezcano and Lary Sorensen to the St. Louis Cardinals for Rollie Fingers, Ted Simmons and Pete Vuckovich.

• February 1, 1985: Dave LaPoint traded by the St. Louis Cardinals with David Green, Gary Rajsich and Jose Uribe to the San Francisco Giants for Jack Clark.

Billy Cox and Preacher Roe:

a) Traded by the Pirates with Gene Mauch to the Dodgers for Hal Gregg, Vic Lombardi and Dixie Walker on December 8, 1947.

b) Traded by the Dodgers to the Orioles for minor leaguers Harry Schwegeman and Johnny Jancse and $50,000 on December 13, 1954.

Mickey McDermott and Tom Morgan.

Feb 1957: from Yankees to Athletics with Rip Coleman, Milt Graff, Billy Hunter, Irv Noren and PTBNL, for Wayne Belardi, Art Ditmar, Jack McMahan, Bobby Shantz and PTBNL.

Nov 1957: from Athletics to Tigers with Billy Martin, Lou Skizas, Tim Thompson and Gus Zernial, for Kent Hadley, Frank House, Duke Maas, Jim Small, John Tsitouris, Bill Tuttle and PTBNL.

Bill Wight and Hoot Evers were twice traded for each other, in deals involving four different teams.

Jun 1952: between Red Sox (Bill Wight, Walt Dropo, Fred Hatfield, Don Lenhardt and Johnny Pesky) and Tigers (Hoot Evers, George Kell, Johnny Lipon and Dizzy Trout)

Jul 1955: between Orioles (Hoot Evers) and Indians (Bill Wight)