diff --git a/Userland/Games/Hearts/Game.cpp b/Userland/Games/Hearts/Game.cpp
index ee0469fd1e..d17fa9097b 100644
--- a/Userland/Games/Hearts/Game.cpp
+++ b/Userland/Games/Hearts/Game.cpp
@@ -161,6 +161,32 @@ void Game::timer_event(Core::TimerEvent&)
     update();
 }
 
+bool Game::other_player_has_lower_value_card(Player& player, Card& card)
+{
+    for (auto& other_player : m_players) {
+        if (&player != &other_player) {
+            for (auto& other_card : other_player.hand) {
+                if (other_card && card.type() == other_card->type() && hearts_card_value(*other_card) < hearts_card_value(card))
+                    return true;
+            }
+        }
+    }
+    return false;
+}
+
+bool Game::other_player_has_higher_value_card(Player& player, Card& card)
+{
+    for (auto& other_player : m_players) {
+        if (&player != &other_player) {
+            for (auto& other_card : other_player.hand) {
+                if (other_card && card.type() == other_card->type() && hearts_card_value(*other_card) > hearts_card_value(card))
+                    return true;
+            }
+        }
+    }
+    return false;
+}
+
 #define RETURN_CARD_IF_VALID(card)     \
     do {                               \
         auto card_index = (card);      \
@@ -177,8 +203,15 @@ size_t Game::pick_card(Player& player)
             auto clubs_2 = player.pick_specific_card(Card::Type::Clubs, CardValue::Number_2);
             VERIFY(clubs_2.has_value());
             return clubs_2.value();
-        } else
-            return player.pick_low_points_low_value_card();
+        } else {
+            auto valid_card = [this, &player](Card& card) {
+                return is_valid_play(player, card);
+            };
+            auto prefer_card = [this, &player](Card& card) {
+                return !other_player_has_lower_value_card(player, card) && other_player_has_higher_value_card(player, card);
+            };
+            return player.pick_lead_card(move(valid_card), move(prefer_card));
+        }
     }
     auto* high_card = &m_trick[0];
     for (auto& card : m_trick)
diff --git a/Userland/Games/Hearts/Game.h b/Userland/Games/Hearts/Game.h
index 560ca64ecc..79c323d71a 100644
--- a/Userland/Games/Hearts/Game.h
+++ b/Userland/Games/Hearts/Game.h
@@ -45,6 +45,8 @@ private:
     Player& current_player();
     bool game_ended() const { return m_trick_number == 13; }
     bool is_winner(Player& player);
+    bool other_player_has_lower_value_card(Player& player, Card& card);
+    bool other_player_has_higher_value_card(Player& player, Card& card);
 
     void start_animation(NonnullRefPtrVector<Card> cards, Gfx::IntPoint const& end, Function<void()> did_finish_callback, int initial_delay_ms, int steps = 30);
     void stop_animation();
diff --git a/Userland/Games/Hearts/Player.cpp b/Userland/Games/Hearts/Player.cpp
index ab129f4739..021d79001f 100644
--- a/Userland/Games/Hearts/Player.cpp
+++ b/Userland/Games/Hearts/Player.cpp
@@ -6,28 +6,39 @@
 
 #include "Player.h"
 #include "Helpers.h"
+#include <AK/QuickSort.h>
 
 namespace Hearts {
 
-size_t Player::pick_low_points_low_value_card()
+size_t Player::pick_lead_card(Function<bool(Card&)> valid_play, Function<bool(Card&)> prefer_card)
 {
-    int min_points = -1;
-    int min_value = -1;
-    int card_index = -1;
+    struct CardWithIndex {
+        RefPtr<Card> card;
+        size_t index;
+    };
+    Vector<CardWithIndex> sorted_hand;
     for (size_t i = 0; i < hand.size(); i++) {
         auto& card = hand[i];
-        if (card.is_null())
-            continue;
-        auto points = hearts_card_points(*card);
-        auto value = hearts_card_value(*card);
-        if (min_points != -1 && (points > min_points || static_cast<int>(value) > min_value))
-            continue;
-        min_points = points;
-        min_value = static_cast<int>(value);
-        card_index = i;
+        if (card)
+            sorted_hand.empend(card, i);
     }
-    VERIFY(card_index != -1);
-    return card_index;
+    quick_sort(sorted_hand, [](auto& cwi1, auto& cwi2) {
+        if (hearts_card_points(*cwi1.card) >= hearts_card_points(*cwi2.card))
+            return true;
+        if (hearts_card_value(*cwi1.card) >= hearts_card_value(*cwi2.card))
+            return true;
+        return false;
+    });
+
+    size_t last_index = -1;
+    for (auto& cwi : sorted_hand) {
+        if (!valid_play(*cwi.card))
+            continue;
+        if (prefer_card(*cwi.card))
+            return cwi.index;
+        last_index = cwi.index;
+    }
+    return last_index;
 }
 
 Optional<size_t> Player::pick_low_points_high_value_card(Optional<Card::Type> type)
diff --git a/Userland/Games/Hearts/Player.h b/Userland/Games/Hearts/Player.h
index be1febd6a9..d7737951fe 100644
--- a/Userland/Games/Hearts/Player.h
+++ b/Userland/Games/Hearts/Player.h
@@ -21,7 +21,7 @@ public:
     {
     }
 
-    size_t pick_low_points_low_value_card();
+    size_t pick_lead_card(Function<bool(Card&)>, Function<bool(Card&)>);
     Optional<size_t> pick_low_points_high_value_card(Optional<Card::Type> type = {});
     Optional<size_t> pick_lower_value_card(Card& other_card);
     Optional<size_t> pick_slightly_higher_value_card(Card& other_card);