As a mental experiment, I decided to throw together a list of four fights that I think might've dramatically changed the context of Joe's career, made him and his camp truckloads of money, and silenced any and all debate about his list.  I think if he won these fights, we could have seen B-Hop/Calz duke it out in 2006.  And win or lose that, he still might've recieved one of the least controversial tickets to Canastota in the history of boxing.

In attempting to retro-fit Joe's career, I've tried to locate the path of least resistance to international mega-stardom.  I think they would also have helped him to retire by age thirty-three, stupendously wealthy and a sure-thing for the Hall of Fame.  

*
(June 1999)
Joe fought:  Rick Thornberry
Joe should've fought:  Vinny Pazienza

What would've it proved?  Ultimately, not much.  But Joe would've got to publicly retire an iconic boxing figure, probably by knockout, and made his American debut in one fell swoop.  Instead, Paz contended the IBO championship that spring with Dana Rosenblatt.  If Joe's people wanted some free press, a highlight reel KO, and a American "name" fighter, he could've gotten it all at once.  Plus, Paz wouldn't have been difficult to negotiate with at all.  He probably would've even flown out to England to get wailed on.

*
(December 2000)
Joe fought:  Richie Woodhall
Joe should've fought:  Sven Ottke

This is a no brainer.  For a fighter like Joe, three years is 23 months too long to let a fraud like Ottke live.  Joe would've been hailed as an international hero for beating Das Phantom to a bloody pulp.  His camp should've given in to every single demand to make this fight happen.  As his countryman Witter recently did with Hatton, Joe should've offered to fight him for free.  He should've also offered to fight him on German soil, and promised to sing "Deutschland, Deutschland Uber Alles" in between rounds.  

Never mind those shifty German judges.  The unification would've been well worth the risk.  And if it turned out to be a robbery - hey who HASN'T been robbed by Ottke!  No shame in that!  Besides, if it happened, at least would've been a massive, public robbery in broad daylight, and would've gotten lots of free international press and sympathy.  

And if you win?  Though my version of Joe and Warren offered to take a bath moneywise on this first fight - they also made sure that the contract guarantees the rematch is held in England, and that Team Joe gets the biggest slice.   On the other hand, if Joe's team thought that simply holding on to the WBO and an "O" would eventually bring the big names and money sailing off to England - well we saw how that strategy worked out, didn't we?

*
(October 2001)
Joe fought:  Will McIntyre
Joe should've fought: Antwun Echols (OR scoop up another belt)

At this point, Joe has likely assassinated Sven again in a spring rematch in Cardiff .  Politics (and concern for good hygiene) probably would've kept Zags away from the scrum for Hilton's WBC crown.  Still, in this alternate universe where the stain of Sven has been wiped away, who knows?   There may be an extra belt lying around somewhere, or wrapped around a dainty waist like Beyer or Lucas or one of those guys.  If so, nab it Joe!  It belongs to you!  

But say that can't happen?  If you're now a dual belt-holder and feel like taking out someone's trash, why not B-Hop's?  Calzaghe could've drawn a laser beam on Antwun's skull early in his run at 168.  You don't think Echols' would've come running for Joe's belts rather then fight (and utterly destroy) the undertalented Charles Brewer for that shoestring called the NABA?  Instead, Joe actually waited around another year and let BREWER come running!  Oh well.

Meanwhile, HBO would've picked up the Echols fight for sure, casting Echols as the underdog challenger to Joe's reign.  And as far as an attention getter, this would now provide a proper stage for Joe to shout across the oceans at Roy Jones Jr.  And by now, Roy may have started to (vaguely) pay attention.

*
(December 2002)

Joe fought:  Tocker Pudwill! (standing in for Thomas Tate!!)
Joe should've fought:  Roy Jones Jr.

Yep.  If he was well-managed enough, I think Joe could've gotten a main event with Roy Jones by 2002 and negotiated an okay deal for himself in the process.  At the very least, he wouldn't be fighting this past-it fill-in for an also-ran.   And let's not quibble over what weight it's fought at.  If anything, Joe has already proven he is the man at 168 by now, and should've moved up in weight himself.  Then, he wouldn't be risking his laurels, and would have a shot at gigantic paydays for the rest of his career.  

Even if he lost, he would be called "courageous," could convincingly claim that he was stepping out of his comfort zone in weight, and return to his 168-lb throne a wealthier and more prominent figure in the sport.  Instead, his countryman Woods ran off to the states to grab a beating and a fat paycheck.  Woods is a okay fighter, but Calzaghe is leagues faster, far more talented and a southpaw to boot.  It would have been one hell of an exciting fight.

And if he won?  Joe-mania!  He would've been an internationally renowned celebrity, wearing more metal around his waist then Clubber Lang wore around his neck.  Shrines would have been erected to "The Great Joe Calzaghe: The Man who Saved Boxing, etcetera, etcetera."  Ten years from now, guys would have said stuff like "Floyd?  Floyd who?  Oh Mayweather.  Yeah he was okay, I guess.  But he was nothing compared to the Dragon.  That guy is a damn legend."  

Well, okay, I guess that's going too far.