With the increased acceptance of capital market efficiency, there has been a significant increase in the money managed on an indexed basis. Several methodologies are available to replicate the target index. In this paper, we discuss the problems of (1) defining suitable performance objectives and tracking error that scale properly over the entire management period and (2) implementing an optimal investment strategy when full replication of an index is not deemed suitable. We then argue that clustering might be a viable methodology for building parsimonious tracking portfolios. With suitably defined distances between the time series of asset prices, clustering 'discovers' the correlation and cointegration structure of an index. Sampling the clusters with appropriate heuristics and optimization techniques, an optimal tracking portfolio can be constructed. One advantage of this approach is that it eschews the difficulties and computational burden of density forecasts and full optimization.