There were also design problems in that some of the outfits it put Djokovic in weren’t popular in the United States, where the biggest market exists to sell high end tennis gear.

But the biggest problem was distribution. Many of Djokovic’s Grand Slam outfits never even made to the United States, including the apparel he wore when he won last year’s US Open.

“We preordered all this apparel and it was always either shorted or we didn’t get it at all,” said Brian Hirshfeld, owner of Holabird Sports, a tennis specialty retailer in Baltimore. “It was an insult to our industry, to the brand and to him.”

One insider tells CNBC that there were constant fights between the Tacchini reps in Italy and the United States. Those battles were centered around disagreements over money owed by distributors, priority given to European stores on shipments, and suggested prices that priced out much of the marketplace. Tacchini polo shirts often retailed for $80, $20 more than a Nike tennis shirt of a similar make.

The only way one US retailer, Tennis Warehouse, was able to carry Djokovic’s Tacchini gear exclusively in the US, is that it was shipping gear that it had received from its European affiliate.

“They were handed the perfect storm with Djokovic and they couldn’t deal with it,” said another insider.

Sergio Tacchini was never able to deal with Djokovic’s success. In September, CNBC detailed how the company had dropped the ball on the Djokovic deal.

“In order to become a big brand, you have to get lucky and sign a rock star,” Greg Wolf, who runs Midwest Sports in Cincinnati, told CNBC at the time. “They did that. That’s the easy part. But they can’t keep paying him if they don’t know how to backfill the product.”

Tacchini was bought for $42 million in 2008 by Chinese business man Billy Ngok, who is managing director of a company called China Environmental Energy Holdings, which has business in Djokovic’s native Serbia. After Djokovic won Wimbledon last year, Ngok traveled with Djokovic to Serbia, where there was talk of producing Tacchini gear there.

Multiple Serbian publications are reporting that on Wednesday Djokovic will sign with Japanese clothing brand Uniqlo, who already has Japanese tennis player Kei Nishikori on its roster.

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