It has been 19 days since the announcement that IAC/InterActive Corp. had agreed to buy search engine Ask Jeeves for almost $1.9 billion in an all-stock transaction; in the search engine industry, that’s plenty of time to evaluate the deal, examine its strategic underpinnings, and project a future course for the combination of Ask Jeeves’ search assets and IAC’s content properties.

Assuming that the deal goes through by mid-year (despite a stockholder lawsuit and persistent rumors of other, more generous suitors for Jeeves) that’s a lot of combining. IAC’s properties literally run from A (Anyway.com, a French travel booking site) to Z (ZeroDegrees, developer of social networking software.) The holdings in between break out into a few categories:

* Travel (Expedia, Hotels.com, Hotwire, TripAdvisor, Travelscape and a number of specialized sites for campers, timeshares and corporate travel)

* Entertainment (Ticketmaster, CitySearch, Evite)

* Personals, dating services (Match.com, udate.com)

* Financial services (GetSmart, LendingTree)

* Real Estate (Domania, RealEstate.com)

* And of course, shopping (HSN.com, the Home Shopping Network cable property, and the newly-minted Gifts.com, an interactive source for personalized gifts launched simultaneously with the Ask Jeeves announcement)

On Ask Jeeves’ side of the equation, the search engine includes as assets its Excite.com portal, the IWon.com loyalty-based portal, and the MaxOnline advertising sales network. Possibly most important of all are Bloglines, the free online aggregator for blogs, which the company is in the process of acquiring; and Teoma, the actual engine that powers Ask Jeeves’ various search sites. The Teoma engine algorithm has attracted a lot of praise since Teoma’s launch in 2002, for its ability to refine a search and drill down into communities, coming up with pages that are ranked by authority (i.e., links) but in a more dynamic way than Google.

With assets like those waiting to be cross-promoted, small wonder that the first word on everyone’s lips following the buyout announcement was “synergy”.

But the picture is more complicated than that. For one thing, IAC has filed plans to spin its travel-related sites off as a separate public company under the Expedia brand, with Diller as chairman of both. For another, Diller has always taken a curmudgeonly view of the “s-word”, and in fact told a business reporter in early March that “Synergy is too constraining… Everything has to be hard-wired. If the opportunistic gene is the biggest part of you, it conflicts with this executional, rationalized, one-company approach.”

With that view in mind, Diller and other IAC executives have stressed that they believe Ask Jeeves is a good buy in and of itself. It’s the third most recognized search brand, Diller told analysts, but controls only 3% of Internet searches and ranks fifth in market share. With a burgeoning market for paid search advertising expected for at least the next five years, that translates into growth potential.

“We are convinced all this hyper-growth is still at the beginning stage and expect targeted direct selling to take ever larger slices out of the media pie,” Diller said. “Only four or five players will thrive in this market, and because of that, a player like Ask has the greatest opportunity for gaining market share.”

And access to IAC’s capital resources should be instrumental in helping Ask Jeeves grab that additional share. “Ask Jeeves is obviously a survivor of the post-bubble economy,” says Josh Stylman, a managing partner of online marketing firm Reprise Media. “They continually push the envelope in terms of innovation, and if you ask search purists, they’ve been more than holding their own with Google, Yahoo and MSN. But they don’t have the deep pockets that those guys have. And as search gets more aggressive, requiring synergies in business models and d big corporate backers, they were poised to lose that war. Now Jeeves is aligned with a company that’s still smaller than Google, Yahoo or MSN, but they’re at least a real corporate player.”

IAC’s ownership should nudge Ask Jeeves out of its long-held position as a “tweener” search company, says Stylman—stuck between the full-fledged networks of Google and the other titans and the “scrappy upstarts” of search like Clusty and Amazon’s A9.

That’s not to say that synergy of a sort isn’t at work in the deal. Many of IAC’s properties are small vertical local search sites in themselves—for local events (CitySearch), for travel (Expedia et al), or for other local singles (Match.com). That could make Ask Jeeves a serious platform from which to launch an offensive on local search, says Frederick Marckini, CEO of iProspect. “By having an actual search engine, [IAC] now has a unique ability to leverage all those other holdings,” he says.

The vertical approach to search may provide a valuable point of difference for Ask Jeeves, agrees Stylman, especially in contrast to Google and Yahoo, which are aiming to be all things to all people. “Given the way IAC is set up and their expertise in a number of categories including travel, there’s undoubtedly an opportunity for them to take the Ask Jeeves/ Teoma search technology, layer it on top of those properties, and create a very specialized search service.”

Peter Hershberg, another partner at Reprise, points out that search constitutes a different kind of asset than any destination Web site and therefore can’t help but operate synergistically, despite Diller’s public pronouncements. “Search transcends the browser,” he says. “It’s less a destination than a utility, to help people find what they’re looking for among all this content creation.” Give users of these vertical searches the ability to create their own content—reviews, commentaries, etc.—with the capabilities that Ask Jeeves’ Bloglines asset possesses, and you could wind up with a thriving set of user micro-communities centered around these IAC properties.

Diller’s entry into search raises other possibilities. He is, after all, one of the pioneers of interactive television, through the Home Shopping Network, and he has an extensive media background from years helming both the Fox Network and Paramount Pictures. With Google and Yahoo both testing video search, some observers detect a growing possibility that the search market could be poised to grow beyond the Internet within a few years, into cable TV and entertainment content.

And then there’s the question of advertising beyond paid search with contextual or behavioral networks. Ask Jeeves’ natural-language query format gives it a great advantage over other search engines when it comes to deducing what users are really looking for. “The Ask Jeeves search interface creates a longer query,” says Marckini. “On any other search engine, you get a one- or two-word search. On Ask Jeeves, you often get a question, which is phenomenal marketing intelligence to the Web site owner.” That kind of insight into users can help Web site managers optimize for greater customer retention.

It can also help understand who’s coming to the site and why, and that can lead to the placement of ads targeting user behaviors rather than keywords. Ask Jeeves has a contract to place Google search ads that runs until 2007, and in fact derives about 70% of its revenue from those ads. But set down in the midst of all this new IAC content, Ask Jeeves may begin to accelerate a notion that was first introduced when it announced it would buy Bloglines: a behavioral network, serving up ads based on the knowledge it has acquired about users’ interests from these micro-communities.

“The RSS feeds that I’m subscribed to speak volumes about what I’m interested in,” says Hershberg. “And now that Ask Jeeves has that understanding about what I’m looking at every day, they could aggregate that data about me and target ads to me across Ask Jeeves, and now across the IAC properties as well.” That could also work for other properties; for example, Ask Jeeves’ IWon portal, which gives cash prizes for clicking on Web links, signs up 250,000 new registered users each month

This melding of search and behavioral data is something that Ask Jeeves’ competitors are also approaching, but from different vantage points. For example, Microsoft has said that its newly unveiled MSN AdCenter pay-per-click platform will offer demographic data culled from its millions of registered users of MSN services including Hotmail and MSN Messenger. Yahoo also has large volumes of user data that can serve to target ads based on behavior. Even Google’s recent decision to purchase Web analytics firm Urchin Software, announced last week, can be seen as a move toward studying and segmenting Web behavior for more accurate targeting.

“The search wars are turning into behavioral data wars on a lot of fronts,” says Hershberg. “And given the fact that many of its biggest competitors can target this way, it makes sense that a combined Ask Jeeves/ IAC would want to compete on that front as well. And if they do move in that direction, they’ll probably accelerate things and make the move sooner rather than later.”