Looks like

Janus

managers might finally get the chance to wipe one of their most public missteps off the books.

On Wednesday, online health concern

WebMD

(HLTH)

filed paperwork with regulators that will give the top-selling Denver fund shop the chance to sell the 15 million restricted shares Janus fund managers

bought for their funds back in January. At the time, Janus stock-pickers paid $62 a share, but shares were trading off 15% at $10.25 on Thursday afternoon, leaving Janus' $930 million restricted-share investment worth about $153.8 million.

Janus officials weren't immediately available for comment, but the filing reflects the terms of the initial private-placement arrangement. The filing doesn't require them to sell their sagging stake and Janus managers cannot sell any restricted shares until the

Securities and Exchange Commission

approves the filing.

Fund companies, particularly large ones, often buy shares privately from a company, rather than buy them on an exchange where large purchases often drive stock prices up. Private placements give fund managers the chance to buy big chunks of a company at a set price. The catch is that they typically have to agree to hold the shares for a set period of months or even years -- hence, the "restricted" label.

Big fund shops such as

Invesco Funds and

Munder Capital Management have also struck private stock deals this year. In March

TheStreet.com

sifted the fund universe for those that skip the markets and buy restricted shares directly from companies.

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When WebMD announced the deal it seemed like a bargain. The $62 price tag was more than 6% below the stock's trading price; news of Janus' hefty investment sent the stock higher initially. But it's been a

disaster for Janus ever since.

WebMD, which is building a system of Web-based services to streamline HMO enrollment, data and claims processing for insurers, medical professionals and pharmaceutical companies, has posted widening losses and executed a string of acquisitions that have weighed on its shares. Since Jan. 1, the stock is off more than 67%.

Many of Janus' tech-heavy funds that got the restricted shares, such as

(JAVLX)

Janus Twenty and

(JAGTX) - Get Report

Janus Global Technology, have been selling their common or nonrestricted WebMD shares. Through March 31, the two funds sold more than 2.5 million shares, or about 1% of the company, according to

Morningstar

.

Like

many of Janus' aggressive stock funds, a shaky year for tech stocks has hit this pair. Janus Twenty's 9.5% loss this year puts it behind more than 90% of its large-cap growth peers, while Janus Global Technology's 3.1% year-to-date loss places it below the average tech fund, as well. Both funds are closed to new investors due to steep inflows following a sizzling 1999, when the firm's average stock fund gained more than 80%.

While presenting at the

Morningstar Conference

at the end of

June,

(JAMRX) - Get Report

Janus Mercury fund manager Warren Lammert said the firm regretted the WebMD gaffe, but expected to continue striking private deals with companies in the future.