diff --git a/modules/reitit-core/java-src/reitit/Trie.java b/modules/reitit-core/java-src/reitit/Trie.java
index 55250fdc..b9b3b167 100644
--- a/modules/reitit-core/java-src/reitit/Trie.java
+++ b/modules/reitit-core/java-src/reitit/Trie.java
@@ -67,6 +67,8 @@ public class Trie {
 
   public interface Matcher {
     Match match(int i, Path path, Match match);
+
+    int depth();
   }
 
   public static StaticMatcher staticMatcher(String path, Matcher child) {
@@ -98,6 +100,11 @@ public class Trie {
       return child.match(i + size, path, match);
     }
 
+    @Override
+    public int depth() {
+      return child.depth() + 1;
+    }
+
     @Override
     public String toString() {
       return "[\"" + new String(path) + "\" " + child + "]";
@@ -124,6 +131,11 @@ public class Trie {
       return null;
     }
 
+    @Override
+    public int depth() {
+      return 1;
+    }
+
     @Override
     public String toString() {
       return (data != null ? data.toString() : "nil");
@@ -171,6 +183,11 @@ public class Trie {
       return null;
     }
 
+    @Override
+    public int depth() {
+      return child.depth() + 1;
+    }
+
     @Override
     public String toString() {
       return "[" + key + " " + child + "]";
@@ -200,6 +217,11 @@ public class Trie {
       return null;
     }
 
+    @Override
+    public int depth() {
+      return 1;
+    }
+
     @Override
     public String toString() {
       return "[" + parameter + " " + new DataMatcher(data) + "]";
@@ -217,6 +239,7 @@ public class Trie {
 
     LinearMatcher(List<Matcher> childs) {
       this.childs = childs.toArray(new Matcher[0]);
+      Arrays.sort(this.childs, Comparator.comparing(Matcher::depth).reversed());
       this.size = childs.size();
     }
 
@@ -231,6 +254,11 @@ public class Trie {
       return null;
     }
 
+    @Override
+    public int depth() {
+      return Arrays.stream(childs).mapToInt(Matcher::depth).max().orElseThrow(NoSuchElementException::new);
+    }
+
     @Override
     public String toString() {
       return Arrays.toString(childs);
diff --git a/modules/reitit-core/src/reitit/trie.cljc b/modules/reitit-core/src/reitit/trie.cljc
index a1f3aa9c..a6417423 100644
--- a/modules/reitit-core/src/reitit/trie.cljc
+++ b/modules/reitit-core/src/reitit/trie.cljc
@@ -85,7 +85,7 @@
                   (assoc-in node [:children path] (-insert (-node {}) ps data))))]
     (if-let [child (get-in node' [:children ""])]
       ;; optimize by removing empty paths
-      (-> (merge-with merge node' child)
+      (-> (merge-with merge (dissoc node' :data) child)
           (update :children dissoc ""))
       node')))