It's the rule of 'The Path of Least Resistance'. It is that people, like electricity, will usually go down the easiest route to achieve something, e.g. fame, wealth, fitness, cup of tea, CK's coat.... Ergo, most footballers will look to win things in the easiest possible way such as by joining a club that has more recently won something than a club that is on the cusp of winning something but still might actually win something. Basically, they want the shiney baubles for the least effort. Manchester City have a greater chance of winning something than Spurs because they have recently (or more recently) won a trophy. This is dressed up as an 'achievement' even though the likes of Scott Sinclair and Jack Rodwell technically have Premiership titles to their names even though they actually did sod all. It's like passing your exams by copying chunks of the brainy kids work and passing it off as your own.
The real test of character and drive are those who try to achieve the same goals but by not always taking the most obvious (or least resistant) route.