5. San Diego Padres
How aggressive is team president A.J. Preller? Of the nine most expensive outside free agents ever signed to a Padres contract, six (including the top three) were signed by Preller. There have been more misses than hits.
The player who put his name to the richest Padre contract, however, was not a free agent at all. He was and is suspended shortstop Fernando Tatis Jr. The Padres might like to forget it, but over the winter of 2020-21 they committed to Tatis to the tune of $340 million through 2034.
In a factoid that may qualify for Bizarroworld, it also means that a guy who appears to be a fifth wheel — they don’t need a shortstop and nobody’s sure he can play outfield — is the only player in baseball who knows exactly where he’ll be playing and for how much money in 2034.
The Padres’ commitment to their disgraced shortstop is so stretched out that it does not translate to the richest for average annual value. That distinction belongs to third baseman Manny Machado, who signed a 10 year, $300 million contract prior to the start of the 2019 season. That works out to an even $30 million per season.
Preller has never managed to land a more expensive free agent than Tatis or Machado, but he’s come close. He famously made a late and unsuccessful run at Aaron Judge a few weeks ago. Prior to the start of the 2018 season, Preller locked up first baseman Eric Hosmer for seven seasons and $144 million. In 2015 pitcher James Shields signed for four seasons at $75 million.
Then there was pitcher Drew Pomeranz, four years, $34 million, in 2020. Jurickson Profar, three years, $21 million followed in 2021.
With the exception of Machado, every one of those signings looks questionable at best right now.