Possible landing destinations for a MSG V, including the Farley Building annex on 9th Avenue west of the current arena.

B/.dropcapig news last week in New York City: the City Council voted 47-1 to extend Madison Square Garden's operating permit for 10 years only, effectively putting the World's Most Famous Arena on extended life support in its current location above the dangerously overcrowded, dilapidated Penn Station. While MSG chairman James Dolan's reaction to the news was – to say the least – tepid, it seems like the wheels are in motion for the City and the Garden to find a location for a new arena – it would be MSG's fifth incarnation – soon.

Despite sinking nearly $1 billion into a 3-year renovation project that wraps up this summer, the Garden remains old and cramped – it's one of North America's oldest major arenas still in use. And figure that by 2023 even these latest upgrades could be outdated as new technologies and sports industry trends make today's state-of-the-art facilities obsolete. By then, the Dolans will have recouped most – if not all – of their $1 billion investment (which they made with open eyes, not knowing whether the operating permit would be extended at all, let alone indefinitely as they had requested) through increased revenue from higher ticket prices and luxury and club suites.

Ambitious projects in New York City – particularly those squarely in the public eye – like the Second Avenue Subway and rebuilding the World Trade Center, for example – never see shovels in the ground as initially planned. So figure the Garden's 10-year operating permit will almost certainly be extended to get all of the stakeholders on board with a plan that makes sense for everyone. But if a move does happen, where might the city try and encourage MSG to build Madison Square Garden V? Here are the top five contenders:

1. Farley Post Office Annex on 9th Avenue

After the dust settles, we think that this is the arena's most likely destination. Why? You may recall that the Dolans had an agreement in principle in 2006 with Vornado to build a new MSG in this location. In exchange Vornado would have built a new office tower where the Garden currently stands and improved Penn Station (primarily by installing a glass atrium that would have flooded the concourse with natural daylight).

But with Brookfield's Manhattan West and Related's Hudson Yards developments now under construction, another new office tower in the neighborhood seems risky even for a developer like Vornado. And with the first phase of the Moynihan Station project also lurching slowly forward, the necessary coordination both above and below grade might make construction prohibitive. Complicating matters further is the annex's landmarked status, which would make any exterior renovations difficult and costly (though possibly entitle the project to federal tax credits that could grease financing efforts). But despite those challenges, the site's proximity to mass transit and the Garden's current location should make it extremely attractive to the Dolans (after all, they were already prepared to move there just a few years ago). In our opinion, not only is this the most likely outcome of the City Council's vote, but we think that building MSG V here is in the Garden's and the city's best long-term interests.

2. Hudson Yards

Although the city came close to building the West Side/Jets/Olympic Stadium here instead of this massive, transformative, mixed-used development, Related's master plan for Hudson Yards does not call for a sports arena. But Hudson Yards is a massive project that won't be completely built out for another decade, at least, so there's plenty of time to make a deal. Could the Garden end up in the same location where it successfully lobbied against that West Side Stadium almost a decade ago? Perhaps: the 7 train extension to 34th Street and 11th Avenue is underway, and 20 acres of public space included in the master plan could be repurposed.

A new Hudson Yards MSG would also be adjacent to the West Side Highway and part of what Related hopes will become a world-class, full-service, mixed-use destination. Becoming part of the fabric of "New York City's next great neighborhood" should be an attractive selling point for the Garden. Of course the drawback to such a location would be the loss of immediate access to the 7th and 8th Avenue subways and the LIRR and NJ Transit at Penn Station that the arena currently enjoys. But that could be mitigated through extra 7 train service or shuttle buses. And building here would allow the arena to rise unimpeded from the ground up, like the Barclays Center – something the Farley Annex and other possible locations can't offer because of their pre-existing site constraints.

3. Grand Central Station

With the East Side Access project underway, LIRR trains will soon terminate in Grand Central. So thousands of workers (many of whom are Knicks and Rangers fans) who used to commute through Penn Station to jobs in Midtown East will have the option to head straight for the East Side. And now, with the city's (somewhat controversial) rezoning plans for the area around Grand Central moving forward, could the city, the Dolans, and a developer identify a parcel of older buildings along Third Avenue or Lexington Avenue, assemble a superblock, and build a new Garden with an office tower on top of it? Nobody has speculated that this is a possibility just yet, and there are lots of moving parts that would need to be juggled simultaneously for it to happen. But an enterprising, sophisticated developer might be able to make it happen, using Grand Central's mass transit connections – and soon LIRR access to boot – as a selling point to the Garden and city officials.

4. The Hotel Pennsylvania

Vornado owns this McKim Mead White-designed hotel, which unsuccessfully fought for landmark status a few years back. Originally the developer had planned to tear it down and build a high rise office tower, but the Manhattan West and Hudson Yards developments had it rethink those plans and it's currently planning on a renovation instead. The reasons why the site could work? It's across 7th Avenue from the current Garden. But the site footprint is narrow and small – much smaller than the Farley Annex on 9th Avenue – and would likely require the assembly of a superblock – perhaps on the north side of 33rd Street – and construction of the arena on a platform above street level. So this is probably at best a longshot.

5. Its Current Location

Big projects in New York City have a way of, well, dying, or at the least being stalled indefinitely. Like the West Side Stadium, the Second Avenue Subway, and the new World Trade Center, large developments can take years or even decades to get off the ground. The Great Recession came close to killing the Barclays Center in Brooklyn, for example. But MSG has deep pockets and, if it chooses to fight a move, it could postpone one indefinitely.

Yet once the Garden takes stock of all of its options, we think it will realize that a bigger, brand-new arena by, say, 2025, when the current Garden will be almost 60 years old, is in its best interests. More importantly for commuters and New York City generally, it's critical to see a new Penn Station serving businesses and commuters for the second half of the 21st century and beyond. We think that once all the options are on the table and vetted by stakeholders, the Garden will end up settled into a new home by sometime in the 2020s.