CLEVELAND -- You can't necessarily judge a city by the quality and vibrance of its downtown area, but it's not the worst place to start. When you look at major American cities, it's insane how difficult it can be to get a sandwich after 10 p.m. We built these cities, constructed whole sprawling communities surrounding them, and then watched as we burnt a hole in the middle. Millions of people organize their entire lives around the opportunities a city provides and yet won't step foot in the place after 6 p.m. You look at these cities, so lovingly mapped out and plotted, and they're abandoned, incredible views with no one looking at them.

We appear to have recognized this American mistake collectively, in the last few years, and attempted to correct it. Downtown revitalization is a city planner's buzzword, and everyone's doing it, from Los Angeles to Cincinnati to Yakima, Wash. We've now accepted that foot traffic downtown is in fact the lifeblood of a city; it brings money, and art, and innovation, and cache. How you organize and energize your downtown can change the whole reputation of your city, almost independent of anything else. Indianapolis has had so much success with its downtown that it's part of the Super Bowl rotation now. Indianapolis.

Here in Cleveland, it's fair to say they're not gaining much traction in this regard. I've been staying at the Doubletree by Hilton, just a few blocks from FirstEnergy Stadium and the Rock and Roll Hall of Fame, and if I stepped out of my hotel at 10 p.m. and yelled, "James Garfield was an overrated President whose beliefs about a bi-metal monetary system were foolish and destructive!" my words would rattle and echo against the buildings, unheard. I've actually found more sheep downtown than people. This downtown is not revitalized. This downtown has a long way to go.

Citizens of Cleveland know this, and they're doing what they can. For a while, they had a hero, a man who was fully invested in changing the city's downtown landscape. He might have even put the planning PowerPoint documents in Comic Sans.

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The next person here who says something bad to me about Dan Gilbert will be the first. It's not just because of the note he wrote after LeBron James left the Cleveland Cavaliers for the Miami Heat. But it's largely that.

"I think [the Comic Sans note] pretty well matched up with how the vast majority of people in this market and this community were feeling, from little kids to old ladies," Gilbert told BusinessWeek's Ira Boudway a few years ago, and I've heard nothing to make me think he was wrong. People here might not necessarily think that now, but at the time, he was saying exactly what everyone was thinking, only cursing a lot less. I wonder if the world would have handled that note a little better had it not ended with that "I PERSONALLY GUARANTEE THAT THE CLEVELAND CAVALIERS WILL WIN AN NBA CHAMPIONSHIP BEFORE THE SELF-TITLED FORMER 'KING' WINS ONE" business. Before that line, it felt like a venting of the spleen, a frustrated man screaming at the gods for his fate. After that line, you just thought Gilbert was delusional. The next line was, "You can take it to the bank," but if we had, we'd be bankrupt right now. Gilbert is still a wealthy man, so it's fair to surmise that, in fact, he didn't take it to the bank, either.

Let's talk briefly about LeBron here, and get it out of the way. The No. 1 thing people here have looked at me about warily, the one question certain to elicit suspicion that I'm just gonna be another writer person getting Cleveland sports wrong, is LeBron. The expression I get when I bring up LeBron is unmistakable: Don't do the LeBron bulls--t. People in Cleveland do not want to look like jilted exes still pining for the one who got away; they want to make it clear that whole business was overblown. The notion that LeBron was too big-time for Cleveland, that the city and its fanbase were forlorn without him, that was something that outsiders created, not Clevelanders. They were mad he left, sure; he's the best player in the NBA. But they are not the lunatic wailers still burning his jersey the way outsiders think they are. They're still sore about the whole thing, but less in a LeBron sense and more in a your dumb city couldn't contain him way. The sense now is less that LeBron is the problem and more that the rest of us are. We're doing fine, they say. Stop acting like we're not.

Anyway, Gilbert's devotion to making the Cavaliers a championship team in the wake of LeBron's exit might have been unrealistic, but it wasn't insincere. In the years after LeBron left, he and his staff went about building up not just the Cavaliers, but Cleveland's downtown itself. Gilbert's response was perhaps not unlike Cleveland's: You think this means you can stop paying attention to us now, but you're wrong.

Gilbert's stamp on downtown is unmistakable. There is of course his Quicken Loans Arena -- or "The Q," as it's listed on directional street signs around town -- right across the street from Progressive Field; the two edifices even share a plaza. (The AHL's Lake Erie Monsters and the Arena League's Cleveland Gladiators, both owned by Gilbert, play at the Q as well.) The biggest casino in town is Gilbert's Horseshoe Casino, which several locals told this non-gambler is "much nicer than it probably had to be." Gilbert is also renowned for helping build up the local tech scene, regularly investing in local businesses, particularly if they agree to have their offices downtown, through his company Bizdom.

Gilbert is beloved for this, almost as much as he is for the Comic Sans letter. But this love comes with a catch, and it's one Clevelanders are sort of getting tired of: Gilbert has another love.

In the last couple of years, Gilbert has averted much of his attention to a town that needs his help even more than Cleveland does: Detroit. He bought the Greektown casinos in Detroit. He moved Quicken Loans' corporate offices to Detroit. His venture capital firm is called Detroit Venture Partners. He has bought many major Detroit buildings, from the Madison Theater Building to the Chase Tower to the Chrysler House. He also lives in the Detroit area, in Franklin, full time; he grew up in Southfield.

Every city that's struggling, that's trying to get back on its feet, that's trying to make its downtown matter again, it, in part, needs a private benefactor: Someone who believes in the city. You need a billionaire. Cleveland's is Dan Gilbert. The problem is that he's Detroit's, too. He might be primarily Detroit's.

Cleveland's downtown has some inherent disadvantages, most notably Burke Lakefront Airport, a small Rich People airport just by FirstEnergy Stadium that takes up a mile-plus of shoreline on Lake Erie that would be extremely desirable location for some waterfront businesses. It's a shame that an airport with no commercial flights can take up such lovely space downtown. Cleveland still needs more businesses here than just Gilbert can provide. Detroit does too. But Cleveland needs Gilbert, and they need him for more than just getting the Cavaliers a championship.

Cleveland might want a title from the Cavaliers, sure, and I have no doubt Gilbert will do all in his earthly power to make that happen. (All told, the Cavs are set up to be better, short-term and long-term, than lots of other NBA teams; ESPN listed them eighth in its NBA Future Power Rankings.) That passion, though -- that Comic Sans Fervor that made Cleveland appreciate him so much -- there is a sense among Cleveland fans that it is distracted now. Maybe that's fair and logical, and maybe it isn't. But if Dan Gilbert were always concerned with what was fair and logical, Cleveland might not love him as much as it does. Cleveland's downtown needs more than just Dan Gilbert. But it also needs more Dan Gilbert.

Email me at, follow me @williamfleitch or just shout out your window real loud, I'll hear you. Point is, let's talk.