Contests are a terrible way to do design. For a designer its work you will likely never get paid for, but it also takes out the whole iterative process working with the client to discussing their needs, researching customers problems and needs, exploring and refining multiple concepts, testing, etc. The map is just one element of a much bigger wayfinding system of signs, messaging and announcements. These considerations get lost when the decision gets turned over to a public vote.
The Massachusetts Bay Transportation Authority (MBTA) held a contest to redesign the subway map. This time the contest lead to a real winner of a map by Mikheil Kvrivishvili,
"Kvrivishvili’s map includes new features that provide customers with more information and more appealing aesthetics, including all surface Green Line stations shown, all SL2 stops shown, an area of the map showing the connections between the Silver Line and the downtown subway stations—enlarged to make it easier for customers to understand how the various Silver Line routes operate—and color-coordinated labels for all of the rapid transit lines."
Where the old T map and some of the other contestants tried to maintain some level of geographic accuracy, Kvirishviki went for a diagrammatic look that simplifies and straightens out the lines on 45 degree grid. Especially for the Green Line that break with geography provides room to label every surface stops and spaces them evenly.
Downtown has also been enlarged with wider station placement to make it easier to see the stations and where the lines connect (though not the Red and Blue lines) in a square downtown.
I don’t know the Boston system well, but at a first glance the redesign is much less cluttered. Hopefully I’ll get the chance to have a better look at the article, the winner, and the other competition entries soon.