Angels fans, raise your hands if you are ready for maximum pain.

In the first round of the 2009 MLB Draft, the Los Angeles Angels selected an outfielder out of Millville Senior High School in New Jersey with the 25th overall pick. Most of the time, even first-round picks taken that low don’t turn into superstars, which is exactly why landing Mike Trout so low in the draft was such a coup for the Angels. It could have been the start of something special.

We know Trout’s story by now. By the beginning of the 2010 season, he was a top 100 prospect in all of baseball, and by the end of that year, he was winning minor-league player of the year awards and considered by many to be the best prospect in the league. Trout would make his major league debut in July 2011 and he has gone on to win Rookie of the Year and three MVPs. He is likely to be a lock to make it into Cooperstown once he calls it a career.

As fortuitous as it was for the Angels to land Trout in the draft, their efforts to build a roster around him have been…decidedly less lucky.

Here are the 5 worst LA Angels moves since Mike Trout was drafted

Building a consistent playoff contender despite having the best baseball player on the planet in the organization proved to be very difficult for LA. Adding Shohei Ohtani for six seasons helped, but many of the moves that the Angels made since the day Trout was drafted either didn’t move the needle much or were actively bad.

We are going to be focusing on the worst of the worst moves since the Angels drafted Trout here. Other mistakes beyond these were made, but evaluating moves the team SHOULD have made is too deep of a rabbit hole to go down, and missing on draft picks is something every team does to a degree. These are the high profile whoopsies, not the coulda/shouldas or moves that just weren’t quite good enough. The only guideline is that when a move was considered, the descriptor “dumpster fire” needed to be applicable to them.

The Vernon Wells Trade

This move ended up foreshadowing how Arte Moreno operated as owner of the Angels. For younger fans, Vernon Wells was actually a hitter with a fairly decent track record back in 2011. He had made three All-Star teams with the Blue Jays while averaging 25 homers a season and an .808 OPS from 2002 to 2010. However, the Angels’ GM at the time, Tony Reagins, was not enamored with the idea of trading for the widely available Wells as he was owed a ton of money, was getting older, and wasn’t exactly an on-base machine.

Moreno, as usual, had other plans, and desperately wanted LA to add Wells. Rumor has it that the rift between Reagins and Moreno was so bad at one point that Moreno threatened to fire Reagins if he didn’t trade for Wells. So, Reagins obliged and sent Mike Napoli and Juan Rivera to Toronto to acquire him. Napoli would go on to play seven productive seasons elsewhere, Wells put up two terrible seasons with the Angels, Reagins resigned months after the trade, and many consider the move to be one of the worst modern trades ever.

Signing Albert Pujols to a megadeal

This one is tough, because the allure of signing a guy like Albert Pujols is hard to shake. He was a surefire Hall of Famer even back then, and in 2011, he was coming off four straight top-five MVP finishes, including a pair of wins. However, it was also clear that Pujols was beginning to decline, and that inking him to a long-term deal at his age (real or fictitious) was a risky proposition for any team.

Still, the Angels did give him a 10-year deal that was worth $254 million, and the results were fairly mediocre. He was never an MVP finalist again, made just one All-Star team as an Angel, and averaged just a .761 OPS and 24 home runs a season from 2012 to 2020. This isn’t entirely on the Angels, as Pujols’ body broke down on him, but there were signs before the deal that they should steer clear, and the sheer amount they invested in Pujols kept them from making other moves and made the mediocre return on their investment even worse.

The Josh Hamilton Contract

If the Pujols was an understandable mistake, the Angels would make an even worse blunder the next offseason when Josh Hamilton hit the market. Unlike Pujols, Hamilton already had a very iffy track record, as his career was derailed early on by substance abuse issues. However, he had rebounded and became one of the most feared power hitters in the league by the time he was a free agent before the 2013 season.

True to form. Arte Moreno was incapable of ignoring a flawed slugger and gave his okay to signing Hamilton to a five-year, $125 million deal. While Pujols’ production declined over the course of his many seasons with LA, Hamilton’s absolutely cratered with the Angels, as he hit just 21 home runs in 2013 and injuries robbed him of his ability after that. After an unfortunate relapse with substance abuse during his injury rehab, the Angels traded him back to the Rangers, and Hamilton was out of the big leagues after the 2015 season.

Adding Justin Upton was a disappointment

This is a fun one, because it is both a trade and a contract wrapped up in one. After somewhat recovering from the sting of their previous deals gone wrong, LA was still in need of more help for Trout in their lineup, and the Tigers found themselves facing the prospect of Justin Upton opting out of his contract after the 2017 season. So, LA made the move to trade for Upton that August, Upton did opt out of his previous contract after the season, and the Angels brought him back on a five-year, $106 million deal.

Upton’s first full season with the Angels went well, as he slashed .257/.344/.463 with 30 homers. However, a series of injuries over the next three seasons resulted in Upton slashing just .211/.299/.414 from 2019 to 2021; he averaged playing just 65 games a season. The talent was there, but this was yet another lesson to not give aging veterans lengthy nine-figure deals.

The Anthony Rendon deal was the beginning of the end

Finally, we come to arguably the worst contract in baseball right now — and potentially one of the worst in baseball history, if trends continue — in Anthony Rendon. After the 2019 season, Rendon was widely expected to depart Washington and be among the most sought after free agents in the league due to his status as among baseball’s best pure hitters. The Nationals decided to ink Stephen Strasburg to an equally terrible contract instead, and the Angels signed Rendon to a $245 million deal that haunts the team to this day.

The rest of the story is well-known now. Rendon played well in 2020, but has been physically incapable of staying healthy ever since. On top of his health issues, Rendon has quickly become a villain amongst Angels fans (and baseball fans in general) for his attitude towards the media in general and his tone-deaf comments about baseball not being a priority for him. There is still time for this deal to turn around, as the Angels are going to be paying him $38 million a year through 2026, but the odds are that Rendon’s contract will go down as one of the worst deals of all time and Trout’s entire career in LA will end up being squandered.