Hamilton sees red!
Within F1, the biggest opportunity to present itself to Wolff around this time might have been McLaren, where long time boss Ron Dennis was forced out by new investors and the team struggling to find a principal capable of shaking the squad out of its growing malaise. It's not hard to imagine Wolff spying a big opportunity to step in and establish himself as the linchpin in exactly the way he rapidly rose to the top of the management tree after investing in Mercedes. If so it's hard to imagine Wolff allowing McLaren to rip up its Mercedes engine deal in favour of the ill-fated Honda project. If Hamilton had still been at Woking the two could have quickly bonded, setting up all the building blocks that boosted Mercedes to domination in reality and propelling Hamilton to two or three back-to-back titles - only this time for McLaren.
Or maybe by this time Hamilton - always a canny operator in terms of shaping his career - would already have found a way out of Woking. Massa exited Ferrari at the end of 2013 by which time Alonso had been with the team for four years without making that crucial title breakthrough. With no Mercedes in play, if Hamilton hadn't already been firmly ensconced at Brackley by this point then surely the Scuderia would have come calling? And if Alonso was displeased by that ... well then, too bad. Going to Ferrari in 2014 would have been perfect timing for Hamilton: not only was the previous Red Bull dominance in rapid decline by then, but the latest engine regulations were now in effect - and without Mercedes around as a works team to push for revolutionary hybrid power units it's likely that Ferrari's arguments for something more akin to a traditional V8 package would have carried the day, handing them a crucial advantage for the next few years.
Up to date and full circle
Fans of Alonso will vehemently disagree, but the signs are that Hamilton would have come out on top that year and duly won his second title - as he did in reality with Mercedes. In both real and imagined histories, Alonso would then leave Ferrari the following year, opening up the tantalising prospect of Vettel joining Hamilton at Ferrari in 2015. Maybe Hamilton won their first head-to-head only for Vettel to come out on top in 2016, just as Rosberg managed to dethrone his Mercedes team mate in the actual history we know? Perhaps that could have revitalised Vettel and resulted in them splitting the honours in the ensuing years of thrilling duels.
Or perhaps more likely, just as in our world, the defeat might have galvanised Hamilton to even greater heights and a string of titles. In that case, by the time Charles Leclerc came into view threatening to oust one or other from Ferrari, it would have been Vettel who found himself being hustled toward the exit door - maybe a year or two earlier than happened in reality. Meanwhile Max Verstappen would have doubtless become a force to reckon with at Red Bull, while Valtteri Bottas was now top dog at a surging McLaren thanks to his close partnership with their by now long-established team principal Toto Wolff. A juicy prospect for 2020 before the pandemic rolled in, in both real and imagined worlds.
And just maybe on the sidelines, Mercedes is finally tiring of its passive role merely supplying engines and actively plotting the best way back into the world championship, thinking of which team to buy and who to headhunt to run the operation and drive its cars...