The Chattanooga Lookouts have been Class AA affiliates of the Cincinnati Reds since 1988.

Lookouts players have worn red at Engel Stadium and AT&T Field and could wear it again next season, but what would they look like in Yankee pinstripes or Dodger blue? As the 2008 Southern League regular season enters its final days, the opportunity for Lookouts owner Frank Burke to renew with Cincinnati clearly is dwindling.

“I cannot talk about it,” Burke said this past week. “There is a time to talk about this, and that’s at the end of the season.”

The Lookouts are among eight Class AA affiliates yet to extend their player development contracts with their existing big-league clubs. Five of the eight are Southern League teams, as Carolina has yet to renew with Florida, Huntsville with Milwaukee, Jacksonville with Los Angeles and West Tenn with Seattle.

If Burke seems evasive about the subject, it’s because he has to be.

According to Lori Webb, the Southern League’s vice president and director of operations, a minor league club that discusses a potential partnership with a different big-league organization before the proper time can be fined up to $100,000 by the Minor League Association. Major league clubs caught tampering with minor league affiliates in other organizations can be assessed much larger fines.

Even so, Burke not discussing the Reds is a change from June. Asked then about the likelihood of a player development extension, he said, “Neither one of us is looking toward anybody else.”

Chattanooga’s 21-year relationship with Cincinnati is the second-longest involving current Southern League teams, trailing only the 23-year marriage between Birmingham and the Chicago White Sox that has been extended through 2010.

The Lookouts and Reds got off to a victorious start when Chattanooga won the 1988 Southern League title and Cincinnati pulled a stunning sweep of Oakland in the 1990 World Series. The pairing also prospered earlier this decade, as the Reds opened AT&T Field in 2000 with an exhibition game against Baltimore and returned for exhibitions in 2002 and ’04.

There has not been a big-league exhibition in Chattanooga since, however, and most of Cincinnati’s top prospects lately have spent little time in a Lookouts uniform.

Current Reds outfielder Jay Bruce was rated by Baseball America as the top prospect in the minors after playing last season at high Single-A Sarasota, Chattanooga and Triple-A Louisville, but only 16 of his games were with the Lookouts. Outfielder Drew Stubbs is Cincinnati’s top prospect now, but he played just 26 games with Chattanooga earlier this summer before moving on to Triple-A.

Cincinnati is headed for its eighth consecutive losing season, which has resulted in plenty of turnover. In the past six years, Burke has worked with four Reds general managers and three directors of player development.

Terry Reynolds, the third of those farm directors, admits there soon will come a point where the relationship with Chattanooga is awkward.

“I wouldn’t say we’re there yet,” Reynolds said. “Frank and I had good conversation while I was there a couple of weeks ago, and I think it’s just been an ongoing process that’s taken a little longer than usual. But I wouldn’t say that the chances of renewing are less likely than they were a month ago.

“My hope is that we’re in Chattanooga for a long time. There has been no hesitation from our part at all, so I’m still very hopeful that will be the case and that we’ll be there next year.”

Should Burke not renew with the Reds, he would have to notify the Minor League Association after the Southern League season. A list of big-league clubs and minor league teams seeking new partnerships will be made known Sept. 12-15, and discussions between those teams would take place Sept. 16-30.

Clubs that do not have new agreements by Oct. 7 will be assigned affiliations.

The New York Yankees, who have yet to renew with the Eastern League’s Trenton Thunder, and the Los Angeles Dodgers are the two most recognized franchises that could be available. Having the Yankees in Chattanooga would be strange for Burke, who grew up a Boston fan, and that scenario is highly unlikely.

New York limits travel costs by having a team in the Eastern League, and Thunder co-owner Joe Finley told The Times of Trenton this past week that an extension is imminent.

There is rampant speculation that the Dodgers — who are moving their spring-training base from Vero Beach, Fla., to Arizona — will leave Jacksonville and be replaced by the Marlins. Should that occur, Carolina could go after the Dodgers in a flip-flop, but so could the Lookouts or Southern League teams.

“As a league office, we really don’t get involved with that,” Webb said. “I don’t know if people are just taking their time and are waiting to see where the chips fall. I just don’t know.”

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