Steve Finley, 5 years, 21.5 Million Dollars
The Diamondbacks weren't expected to sign Steve Finley. They didn't think that they had a chance for him prior to the 1999 season. However, to the surprise of many, he chose the snakes and I think everyone is happy he did. While he was 34 at the time, the 5-year deal was certainly a risk. Despite that risk, it was one that paid off handsomely. The centerfielder led the Dbacks to 3 playoff appearances, and a World Series ring.
From 1999-2002, Steve appeared in 598 games and had 348 runs, 538 hits, 110 doubles, 23 triples, 108 HRs, 361 RBIs, 47 stolen bases, and walked 240 times while striking out only 321 times. Furthermore, he hit .276, .357, .502, 111 OPS+ while providing great defense and 13.1 WAR. Combine that with his lone All-Star nod and 2 Gold Gloves, and this contract was easily worth it. Another great deal by the great Jerry Colangelo. If only he was still our owner.