For as long as I’ve been writing and thinking about the art market - roughly a decade, with increasing intensity - there have been two seemingly contradictory phenomena driving its development. I keep wrestling with how to reconcile them, but I haven’t yet, and I hereby throw the paradox onto the Artworld Salon floor for discussion.

The first phenomenon is the surge in what I’ll call “cross-category collecting.” It’s rare to meet someone these days who only collects, say, vintage photography or Old Masters or German Expressionism. Most collectors also buy within several mediums. And within those mediums, people have started to cover much broader swathes of history. As The Economist noted last month: “To some extent, interest is spilling over from hot markets to [Old Masters]: newer buyers who might start out buying impressionist, modern, Russian or contemporary art are increasingly drawn to the big names among the Old Masters. (Many older paintings fit surprisingly easily within contemporary interiors.) But the peculiar confluence of factors that has propelled prices sky-high in other markets has not had as extreme an effect with the Old Masters.”

That brings us to our second trend, much noted among artworld veterans: the erosion of “relative value,” meaning the notion that an artist’s market should reflect their standing compared with all other artists, not just their peer group. Explaining the July round of auction sales in London, Daily Telegraph art-market specialist Colin Gleadell wrote: “Last week a good Bacon sold for more (at £21.6 million) than the two good Monets, and a flashy Damien Hirst (£9.6 million) made almost as much as the much rarer Matisse….For fashion-conscious collectors, a Koons or a Hirst is now worth more than a Rodin and as much as Giacometti.”

And herein lies the paradox: If the collector bases for everything from Old Masters to the avant-garde are becoming more interwoven, shouldn’t more, not less relative-value thinking be reflected in the prices paid? Granted, I do know one contemporary-art collector who turned first to Morandi then toward Old Masters as the prices for contemporary paintings rocketed. But on balance it often seems to me that the various art-market segments are operating in wildly different ways - across even relatively minor increments in art history. So, clearly, though people are buying widely within different genres and generation, they’re not using the same metrics in judging what price they’ll pay for particular pieces. Thoughts?

In a few weeks, “For Sale,” a show curated by Jens Hoffmann, director of San Francisco’s Wattis Institute, will open at Cristina Guerra Contemporary Art in Lisbon. Hoffmann’s statement describes the exhibition as a reflection of the current trend toward curators organizing shows in commercial galleries, a tactic which downplays the space’s art-dealing in favor of its cultural role. Playing slightly deuxième degré, Hoffmann has asked the artists that he selected for works directly reflecting the fact that the show takes place in a commercial context. The artists lists is strong, multi-generational and brainy, including Allora & Calzadila, John Baldessari, Elmgreen & Dragset, Andrea Fraser, Ryan Gander, Louise Lawler, Tim Lee, Jonathan Monk, Raymond Pettibon, Tino Sehgal, and Mario Garcia Torres.

Here’s the interesting twist: “None of the works in the exhibition can be bought individually and the show can only be acquired as a whole. This fact… obstructs the eventual purchase of the art works - it is clearly more expensive and far more complex to acquire a whole show rather than an individual work. While seemingly completely embracing the commercial aspect of the gallery, FOR SALE in fact tries to obstruct routine business.”

I’d love to see this show due its artists and concept, yet I’m especially curious how effective Hoffmann’s dictate will prove in its stated objective. Frankly, I would not be entirely surprised if some collector takes the plunge, given the mixture of hot young names and established stars, plus Hoffmann’s own curatorial imprimatur. (Obligatory disclosure: Hoffmann curates the Art Perform section of Art Basel Miami Beach; we also once survived a kimchi-and-karaoke night out together in Gwangju, Korea.) After all, if art-market history teaches us anything, it’s that the market is endlessly inventive and surprising when confronted with attempts to obstruct or circumvent it. For someone with tons of money and a big display space, who also happens to share Hoffmann’s taste, the Lisbon show could prove an attractive way to turbo-charge their collection. (Or a museum, better yet.) If it “fails,” this concept could prove strikingly successful for everyone concerned.

Walking through the MCA Chicago’s summer photography show recently, I came across the David Robbins piece “Talent,” from 1986. To create it, Robbins had 18 young art stars of that moment, including himself, pose for the sort of glossy airbrushed headshots that actors send casting agents. Two decades later, some of those are names that even a Culture-section scanner would recognize, such as Jeff Koons and Cindy Sherman. Others are around, if not quite stars. And some have moved far from the artworld spotlight. Robbins himself reportedly “became disenchanted with the New York scene and returned to his hometown of Milwaukee, Wisconsin. There, he began to pursue performance art and dot painting in the context of the small-town tradition of the ice-cream social. The first social was held at a local Baskin-Robbins.”

That some stars stay and others fade is not noteworthy. No, what struck me at the MCA was the (coincidentally) side-by-side presence of Peter Nagy and Ashley Bickerton in the matrix. A decade after the picture was taken, in 1996, both seemed to have essentially exited the mainstream artworld, making new lives an ocean away. As the NY Times wrote last year, the early-nineties “art-market dip left Mr. Bickerton’s career, among others, high and dry. He moved out of New York, first to Brazil then to Bali, where he still lives.” The international Herald Tribune in 2005 tracked Bickerton down doing a printmaking project in Singapore. “My career was basically in the toilet,” he recalled. “After the flash and success, there is another test that comes: longevity.” After a mid-nineties hiatus, Bickerton has come back strongly onto the international art market, most recently via Lehmann Maupin gallery. Painter and East Village gallerist Nagy, who had disappeared to Asia around the same time as Bickerton, has successfully recast himself as the leading gallerist working with India’s suddenly sought-after contemporary artists.

Looking across a much broader swath of art history, there was a long period when the influence of Marcel Duchamp was totally undervalued, and likewise the resurgent interest in Francis Picabia, circa 2002, caught many by surprise. We too often tend to view artists’ careers simplistically, as a progression from anonymity to fame and (almost always) back again. But that’s hardly the only model, especially in an artworld that’s growing ever more multifaceted. Journalism may be the first draft of history, but even art history is never written in stone.

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I wonder if anyone is getting guarantees out of the auction houses these days? In a financial market turning south it is a common strategy to buy “put options” before everyone else notices; i.e. contracts to lock in now, a right to sell something in the future, to someone else at a price fixed now, when you think the market as a whole is falling. An Art market equivalent would be to agree with an auction house now to sell a collection later in the year, on condition of sale price guarantees, set now, at current pricing. Always a risk for the auction house (ask Phillips de Pury), in a real down market it can be a disaster. The smart auction houses understand this, of course. If they are nervous about market values, they stop giving guarantees. Perhaps only in some markets. Perhaps in all.

So I repeat my question: does anyone know if auction houses are still offering sales guarantees this year?

Can you cook up a blockbuster? This is what one curator in a prominent London institution (no names) came to ask me, for a series of interviews that may or may not result in the magic formula for big box-office success. There are various ingredients you need for the cauldron of course; a big-name artist, a spectacular debut or once-in-a-lifetime opportunity, a press deluge and an overstuffed gift shop.

Getting thousands of people through the doors of an exhibition every day used to be so easy – bring in Monet, Matisse, Picasso or all three (Motisso?) – and listen to the cash registers ring out. Nowadays the hugely increased financial pressures of staging such mega-exhibitions - from insurance and shipping to marketing and advertising - mean that the anatomy of a blockbuster show is having to change.

Later this year in London there are a couple of old-fashioned crowd-pullers – terracotta warriors and China coming to the British Museum and Tutankhamun at the old Millennium Dome (now ‘The 02’ venue) – but these are tried and tested recipes. Some museums are now resorting to what I call ‘Stealth Blockbusters’, which on the surface promise the big names and jaw-dropping experience, but can often deceive through clever titles or curating by the back door. For example, the Royal Academy (which has cancelled ‘The Arts in Latin America 1492-1820’ from its autumn slot, because it can’t afford to ship the 250 pieces from LACMA) has recently put on ‘The Unknown Monet’ and ‘Impressionists by the Sea’, which were worthy, scholarly shows with few outright masterpieces. However, once given the sheen of blockbuster glamour and the catchy title, they hit the headlines - and presumably their visitor targets.

Robert Storr put it well before unveiling his Venice Biennale: ‘Once you have enthralled the public enough to get them through the doors, one of the greatest tasks of museums and curators is disenthralling.’ But how long do we wait before we come stomping out of our museums demanding our money back for misrepresentation?

I met up with a few artworld friends for drinks last night, and the conversation turned to the Sunday Times piece on Philippe de Montebello’s Met leadership and the inevitable speculations about his successors. Soon after she left us to go have dinner, Alexandra Peers blackberryed me: “Just heard Lisa Dennison has left the Gugg to do business development for Sotheby’s.” Lo and behold, another museum-director slot to be filled! That makes 25 in the United States, based on the Sunday Times article on the Getty’s museum-director training program.

During our cocktails, I had pointed out the fact that at any given moment there seem to be 20-odd open museum directorships and only a half-dozen names in circulation as their likely occupants. Often, of course, those are other museum directors, and when they switch slots, the dilemma remains. Now, musea are not my forte, but from my relatively outside perspective it seems the problem lies in the way that the job has evolved through mission creep over the years. In addition to the classic connoisseurship required, fund-raising and business skills have become a big part of the job, as has the ability to deal with major construction projects and foreign governments. The Getty article quoted Cloisters/Met curator Julien Chapuis saying: “I’m concerned that the next generation of museum leaders will be business people not trained in art history, people who have little knowledge of the collection, which for me is the raison d’être of a museum.” Then again, a museum director needs to have the respect of his curators. As the Guardian reported when London’s National Gallery director Charles Saumarez Smith quit, he was said “to have been undermined by a cabal of his own curatorial staff who belittled his intellect and thought him a poor connoisseur.”

So it seems today’s ideal museum-director candidate would have a PhD in Art History, an MBA, plus several years of Foreign Service and corporate experience under the belt. It’s a tall order, which may explain why it’s so frequently found to be difficult to fulfill, especially outside the top institutions. As I suggested to my drinking companions last night perhaps it’s time to widen the notion of how museums are led: Splitting the job into business and art functions, rather than desperately seeking candidates combining all the skills required in the modern museum era and paralyzing the institution until the ideal candidate surfaces. Thoughts?