C#

public enum PlayerPosition { QB, HB, WR, TE, LT, LG, C, RG, RT, DE, DT, OLB, MLB, CB, FS, SS }

public List<Player> depthChart { get; set; }
public List<Player>[] DepthChart
{
    get
    {
        var result = new List<Player>[Enum.GetValues(typeof(PlayerPosition)).Length];
        foreach (PlayerPosition pos in Enum.GetValues(typeof(PlayerPosition)))
        {
            result[(int)pos] = this.Players.Where(pl => pl.position == pos && pl.CanPlay).OrderByDescending(pl => pl.OVR).ToList();
        }
        return result;
    }

Team t = league.Teams[0];
var depthChart = t.DepthChart;
Console.WriteLine(depthChart);

foreach (PlayerPosition pos in Enum.GetValues(typeof(PlayerPosition)))
{
    Console.Write(pos.ToString() + ':');
    depthChart[(int)pos].ForEach(p => Console.Write(' ' + p.lastName));
    Console.WriteLine();
}