Whether you've been eavesdropping on Southie barstools for the past week or just reading through the Herald's daily Whitey dedication, there's no escaping speculation about what might become of New England's most notorious modern criminal. With that said, as the world waits patiently for updates, we've imagined endings to a saga that's been kindling for decades, and that only now seems to be exploding. We'd be seriously surprised if any of these storylines materialized, but then again, homeboy was living on the beach in Santa Monica, so you never know.
On the ride from his holding cell to the federal courthouse in South Boston, Bulger discovers that a parking spot he reserved in 1994 – just months before going on the run – has been taken by another driver. Upon seeing that the beach chair he clearly placed on Old Colony Avenue is missing, the octogenarian becomes so enraged that he breaks free from his shackles, grabs the wheel of the transport vehicle, and smashes it into the offending Nissan Maxima. In court, Bulger apologizes to the room, explaining, 'It took me half-a-fucking-hour to shovel out that spot.'
In a last-ditch effort to exonerate himself, Bulger identifies dozens of missing persons as his victims, and tells authorities that he can lead them to the bodies. The only problem: he says they're buried in the banks of the Big Dig. Determined to close the book on Whitey once and for all, the feds demolish the entire Central Artery, from Logan Airport to South Boston. Years later, it's discovered that Irish mob contractors secured the bid to re-build the Ted Williams Tunnel, and used the profits to restore the Winter Hill Gang to power.
Matt Damon and Ben Affleck are indicted when it's discovered that Bulger's beachfront Santa Monica apartment was being rented by the two Masshole stars. Upon being accused of harboring one of the FBI's most wanted criminals, Affleck points the finger at Mark Wahlberg, who it is rumored partially based the Entourage character Lloyd Lee on Bulger's gay Chinese-American alter-ego, Righty Burger. In his turn, Bulger is further embarrassed when it comes to light that he was the main inspiration for Gigli.
On death row in Oklahoma where he's convicted of murder, Bulger gives his final interview to longtime nemesis Howie Carr. The talk radio host and Herald columnist obliges, and flies out to deliver Whitey a side helping of 'Gotcha' with his last meal, only to have the tables turned on him. With cameras rolling in the cell, a strapped-down Bulger asks a prison guard to open a manilla folder, which contains evidence that Carr is responsible for orchestrating the Oklahoma City bombing back in 1995.
Deciding he's their best man to run against United States Senator Scott Brown, the Massachusetts Democratic Party taps Whitey to represent them on the 2012 ballot. In addition to name recognition from the recent media storm surrounding his arrest, commonwealth Dems hope that older voters will confuse Bulger for his younger brother, former State Senate president William 'Billy' Bulger, at the ballot box. To rival Brown's trademark barn jacket and pick-up, advisors run ads featuring Bulger sporting his state-issue one-piece beside an antique Paddywagon.
DNA tests reveal that the man believed to be Whitey Bulger is actually Duncan Melendez, a former East Boston mafia enthusiast and stepfather of early-90s freestyle queen Lisette Melendez. Not exactly a Boy Scout himself, Melendez draws ire despite the mistaken identity, and finds himself in the crosshairs of a ruthless media shootout. After his family is harassed by reporters and disappointed tourists alike, Melendez disappears with his lover to parts unknown. He is last seen wearing cataracts glasses on a tour of the Eiffel Tower.
Looking to distance themselves from disgraced speaker Sal DiMasi, the Cognos performance management firm hires Bulger to do its lobbying on Beacon Hill. Despite having no clue how Cognos products can benefit the commonwealth, the technologically ignorant mob moss convinces influential pols to sidestep the prescribed legislative process, and ultimately forces a deal through. In return for his efforts, Bulger earns money to pay his attorneys, who also defend him against charges of rigging software contracts through state legislators.
In an unprecedented move, federal prosecutors allow Bulger to prove his innocence by navigating his way – on skates – through a terrifying gauntlet of neon orange traffic cones. What they didn't realize, though, is that Bulger had more than a decade of practice on the piers along Venice Beach, where he spent his golden years disguised as a mustachioed Rollerblade slalom champ. Using tactics learned from watching Airborne – a little-known but much-adored 1993 in-line interpolation of the BMX film Rad – Bulger triumphantly prevails in the face of FBI bullies, and goes back to terrorizing the Boston underworld.
After seeing the photo of Bulger shirtless in a cowboy costume, Vivid Video and Larry Flynt Publications enter a bidding war to secure the wiseguy to play the Jack Palance role in a pornographic adaptation of City Slickers 2: The Legend of Curley's Gold. A federal judge rules that Bulger is allowed to participate, but must use his earnings to help restore Billy Crystal as the host of the Academy Awards. Whitey agrees to the deal, but winds up stabbing Jon Lovitz at a fund-raising event for doing a bad impression of Jack Nicholson doing a bad impression of him in The Departed.
Whitey Bulger is convicted on multiple counts of murder, and sentenced to either death or way more years than he'll be alive. At the same time, the FBI offers an apology to all families that were harmed by the terror that they helped bring to Boston's streets for decades. Those folks are not just given word that the bureau will no longer tolerate systematic bad behavior, but they're also compensated handsomely. The least likely outcome of all, in this scenario Bulger is remembered as the scumbag egomaniac he is rather than as a badass local folk hero.