Player

var (games=100) = ARGV.map{.to_i}...

define DIE = 1..6
define GOAL = 100

class Player(score=0, ante=0, rolls=0, strategy={false}) {
    method turn {
        rolls = 0
        ante  = 0
        loop {
            rolls++
            given (DIE.rand) { |roll|
                when (1) {
                    ante = 0
                    break
                }
                case (roll > 1) {
                    ante += roll
                }
            }
            ((score + ante >= GOAL) || strategy) && break
        }
        score += ante
    }
}

var players = []

# default, go-for-broke, always roll again
players[0] = Player()

# try to roll 5 times but no more per turn
players[1] = Player( strategy: { players[1].rolls >= 5 } )

# try to accumulate at least 20 points per turn
players[2] = Player( strategy: { players[2].ante > 20 } )

# random but 90% chance of rolling again
players[3] = Player( strategy: { 1.rand < 0.1 } )

# random but more conservative as approaches goal
players[4] = Player( strategy: { 1.rand < ((GOAL - players[4].score) * 0.6 / GOAL) } )

var wins = players.len.of(0)

games.times {
    var player = -1
    loop {
        player++
        var p = players[player % players.len]
        p.turn
        p.score >= GOAL && break
    }
    wins[player % players.len]++
    players.map{.score}.join("\t").say
    players.each { |p| p.score = 0 }
}

say "\nSCORES: for #{games} games"
say wins.join("\t")

Output:

0       0       67      101     19
0       88      100     9       14
0       81      66      100     24
0       56      103     8       27
0       102     70      17      27
0       79      101     29      36
0       100     71      56      31
0       62      104     28      34
103     19      24      6       5
0       49      101     24      19
0       60      22      101     0
0       20      101     30      34
...
...
...
0       101     69      26      91
0       87      101     30      54
0       84      100     17      64
0       52      24      102     17

SCORES: for 100 games
6       28      40      22      4