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#NYvCHI: Front-office acrimony and ties between the clubs

Is New York vs. Chicago poised to take off as an on-field rivalry? That’s still firmly up in the air, though Saturday’s game (3:30 pm ET, NBC) could certainly give relations a firm push in that direction.

What’s not in doubt, however, is a decade marked by acrimony between the two clubs’ front offices, the bulk of the hard feeling emanating from Juan Carlos Osorio’s brief but successful tenure in Chicago, his resignation and ensuing courtship with the Red Bulls.

There were enough hard feelings ahead of the 2008 season for Fire owner Andrew Hauptman to call Osorio out publicly, saying he had “no time or respect for someone who makes a commitment to an organization and walks away 16 weeks later.”

Since then, though, things have settled down considerably – it certainly didn’t hurt that Osorio flopped spectacularly in the Big Apple after reaching MLS Cup 2008 – but the overriding theme between the two clubs recently goes something like this: New York wants what Chicago’s got, whether that be coaches, silverware or Colombian defenders.

Ahead of Saturday’s six-point Eastern Conference clash, we go through the top five most influential coaches and players who spent time with both clubs.

5. Dema Kovalenko

Chicago Fire: 1999-2002, 108 appearances, 26 goals

New York Red Bulls: 2006-08, 35 appearances, two goals

Like everyone else to come on this list, Kovalenko made his name in Chicago, actually maneuvering his way to the Windy City via trade after originally being drafted by the Dallas Burn. He got his feet wet in 1999 before truly breaking out a year later during the Fire’s US Open Cup-winning season, scoring 10 goals and passing out five assists.

After three standout seasons with the Fire under Bob Bradley, Kovalenko moved to D.C. United, where he won an MLS Cup, before landing in New York during the middle of the 2006 season. Injuries marred his career with the Red Bulls, however he still managed 35 appearances, most as a holding midfielder, before moving to Salt Lake then LA prior to retiring in Feb. 2011.

4. Ante Razov

Chicago Fire: 1998-2000/'01-04, 156 appearances, 76 goals

MetroStars: 2005, 18 appearances, six goals

An MLS original, Razov was one of league’s most potent finishers until his retirement in 2009, but his most productive years certainly came in Chicago. He averaged 14 goals from 1998-2000 as the Fire won MLS Cup and a USOC title, then dropped consecutive 14-goal campaigns in '02 and '03 after spending part of '01 in the Spanish second division. With 76 goals, he remains the club’s all-time leading scorer.

It wasn’t all positive for Razov in the Windy City, though, as he was traded to the Crew after an uncharacteristically unproductive 2004 season and an apparent conflict with manager Dave Sarachan. He lasted just seven games in Columbus before rejoining Bradley with the MetroStars. Per usual, he put the ball in the back of the net – six goals in 18 appearances – before moving on to Chivas USA to rejoin Bradley after the manager was relieved of his duties.

3. Wilman Conde

Chicago Fire: 2007-2010, 73 appearances, four goals

New York Red Bulls: 2012-present, 16 appearances, one goal

Part of the first wave of the current crop of Colombians populating MLS rosters, Conde wasted no time becoming a fulcrum of Chicago’s backline, partnering with Bakary Soumare to make up the core of one of the league’s best defenses. He made the All-Star team in his final season with the team in 2009 before moving south to Mexico with Atlas.

While his success with the Fire is well documented, it may be the transfer drama that Chicago fans remember most. Conde joined the team with the intent of linking up with his former boss at Millonarios, Juan Carlos Osorio.

When Osorio left for the Red Bulls after just a few months at the helm, Conde’s desire was to follow his countryman to the bright lights of New York. He publicly demanded a trade that didn’t happen, of course, but the Colombian still found his way to New York eventually, signing with the Red Bulls prior to the 2012 season after his return from Mexico. He'll line up against former teammate Chris Rolfe on Saturday.

2. Juan Carlos Osorio

Chicago Fire: July 2007-Dec. 2007

New York Red Bulls: 2008-Aug. 2009

There may not be a bigger villain in Chicago Fire history than Osorio. After Sarachan was let go after a string of disappointing results halfway through the 2007 season, a driven young former New York assistant arrived in Chicago to help lead the Fire, featuring Cuauhtémoc Blanco and Conde, to the conference final.

Then Osorio unexpectedly resigned and joined the Red Bulls barely a week later. That didn’t sit well with Hauptman, who filed tampering charges that resulted in cash, allocation money and a first-round draft pick changing hands while Chicago reportedly refused to do any further business with New York. Unfortunately for the Red Bulls, Osorio presided over what is perhaps the worst season in franchise history after leading the team to an unlikely MLS Cup appearance during his first season in charge.

1. Bob Bradley

Chicago Fire: 1998-2002

MetroStars: 2003-05

Winning an expansion double seems like something more befitting the Brothers Grimm these days, but that’s exactly what Bradley’s first-year Fire squad accomplished in 1998, capturing the MLS Cup and the US Open Cup. He followed that up with another USOC in 2000, before resigning (sound familiar?) to return to his home state as the MetroStars head man after the 2002 season.

He wasn’t able to replicate the success he enjoyed in Chicago over the course of two seasons with the MetroStars, despite making it to the USOC final in 2003, and his stint in New York was cut short by his dismissal in October 2005. Perhaps his most noticeable accomplishment was kick starting the career of his son, Michael, now a US national team stalwart and Roma player.

Of course, his unceremonious exit from the MetroStars did nothing to dampen his future success with Chivas USA and, of course, the US national team. He was elected into the Fire's "Ring of Fire" Hall of Fame in 2007.