No. 5—October 7, 1969
The Deal—The Phillies sent 1B Dick Allen, INF Cookie Rojas and RHP Jerry Johnson to the St. Louis Cardinals for CF Curt Flood, OF Byron Browne, LHP Joe Hoerner and C Tim McCarver.
This deal represented GM John Quinn finally throwing in the towel by dealing the team's unhappy and controversial slugger Dick Allen. The five tool player is considered by many to be the greatest athlete and most exciting player to ever wear a Phillies uniform.
Just six seasons earlier, Allen was recognized with the National League Rookie of the Year Award for leading the Phillies on a year long flirtation with the pennant that famously ended with a crash landing over the last ten games. Allen went on to have many successful seasons on several teams, including an AL MVP performance in Chicago.
In a roundabout way, a case could be made that the Phillies eventually received close to commensurate value for their talented slugger, but the back story is what pushes this over the top in terms of importance. Curt Flood was the key player in the deal coming from the Cardinals, but when he opted to sue major league baseball rather than report to Philadelphia, it changed baseball and professional sports forever.
The Flood case made it all the way to the Supreme Court, leading to the advent of free agency and arbitration. The Phillies selected Willie Montanez, who contributed a few solid years before he was swapped for Gold Glove center fielder Garry Maddox, a stalwart on the 1980 World Series Championship club.