In 21st century Digital Technology has provided a dynamic platform to presidential candidates who can now have more of a dynamic conversion which happens in the form of dialogues . Presidential candidates can now converse with a lot of voters directly on a one to one manner . The Web today provides a genuine platform for grass root level campaigning as power gets diffused and its a free for all where every body can participate and this is where the presidential candidates can engage the voters. Now if we rewind back and compare the digital campaigns of Barack Obama and Donald Trump we will find that both used digital technology in the best possible manner and both understood remarkably well what was audience expecting from their presidential candiadtes at that point of time. In case of Barack Obama Twitter , Youtube , Facebook & personal web as channels were used extensively where as in case of Donald Trump it was Twitter . So Barack Obama’s case just about everything on digital front was used where as in case of Trump it was mostly Twitter. In Barack Obama’s case the target voters were youngsters where as in case of Donald Trump it was basically of voters of all generations. In Barack Obama’s case the use of digital technology was also to highlight to voters that he represented just the kind of young leadership needed by the country which was in sync with the newer levels of advancement . His political gimmick was to portray himself a forward thinking candidate so that he can attract the young voters . In terms of activity on social media & web Barack Obama was way ahead of his nearest competitor Romney as he posted twice number of blogs on his website and more than twice videos on youtube . He was most active on twitter than any of his rivals. In Donald Trump’s case it was basically understanding the effects just one socila media can have if use it effectively . Donald Trump used Twitter and in fact he had become a Twitter master and was not afraid to say anything relevant directly on Twitter . By doing so he appeared to be just the straight & right guy who could bring certain revolutionary changes required at that time . He did not use all the channels available but he was quite effective in understanding his audience and used a lot of entertainment in his tweets just to engage his audience better. Just like Obam he also hosted Saturday Night Live but his straight unapologetic de manure ensured attracting the largest number of viewers ever.