5 Jimmy Dykes and Joe Gordon
Who? Exactly. This one wasn’t exactly an Earth-shaking deal, but it is to this day, the only time in MLB history that two managers were actually traded for each other. In the middle of the 1960 season, the Cleveland Indians and the Detroit Tigers both felt it was time for a change, and elected to just swap their managers straight up. Gordon headed to Detroit, and Dykes went to Cleveland. Neither team would finish the year above .500.
4 Ozzie Guillen
Ozzie Guillen was a hot commodity back in 2011 when the White Sox were ready to part ways with him. Leading the Sox to a World Series victory in 2005, Ozzie had unfortunately made more headlines with his big mouth than he did with his victories, but he seemed to be a perfect fit for the newly renamed Miami Marlins, who had moved to a brand new stadium and were looking to endear themselves to a largely Hispanic fan base. The Marlins sent two minor-leaguers to Chi-town in exchange for Guillen, who promptly pissed off the entire city when he said he “loved Fidel Castro” in an interview. Guillen lasted one season in Miami.
3 Gil Hodges
Truly one of the all-time greats, Gil Hodges spent the bulk of his career in Dodger Blue. After 12 seasons in Brooklyn, Hodges moved cross-country with the team to LA where he spent four more seasons with the Dodgers before the upstart New York Mets selected him in the 1962 expansion draft. Hodges would retire after only two seasons in Queens, but would return to the team in 1967, this time as a manager, when he was traded from Washington for a pitcher and $100,000. Two years later, in 1969, Hodges led the Mets to one of the most unlikely World Series Championships in league history.
2 Stan Van Gundy
After serving as an assistant coach with the Miami Heat for nearly a decade, Stan Van Gundy was hired in 2003 to take the reins from coach Pat Riley, who was poised to become team president. SVG’s tenure would last two full seasons and a handful of awkward games, after which Pat Riley wanted his shiny toy back. Early in ’05-’06, Van Gundy resigned, though it was hardly his decision, and Pat Riley once again took over. Riley won the NBA title with Shaquille O’Neal and Dwyane Wade, while SVG, who was still under contract, was traded to Orlando in 2007.
1 Jon Gruden
For all of the great things that Oakland Raiders’ owner Al Davis did in his earlier years, his late career was known more for his often-inexplicable decision-making. Case in point, Jon Gruden. Davis had seemingly struck gold when he hired the 34-year-old boy-genius, as Gruden returned the Raiders to the AFC championship and respectability within 4 years of being hired. But their eventual clash of personalities led to Davis trading Gruden in 2002, sending him to the Buccaneers for $8 million and four draft picks. The following season, the Buccaneers won the Super Bowl. They beat the Raiders. Ouch.