Freddie Freeman is making Yankees regret not signing him every single day

After the 2021 season, the New York Yankees had a prime opportunity to shake up what was a dead and embarrassing roster and prepare themselves to capitalize on Aaron Judge's contract year, which, for a second there, seemed like it'd be his last in the Bronx.

Instead, they once again did very little. After another terrible trade deadline that netted them Joey Gallo, Andrew Heaney and Anthony Rizzo (who actually wasn't that great for them over the second half), general manager Brian Cashman re-signed Rizzo, let Brett Gardner go, traded Luke Voit, Gio Urshela and Gary Sánchez, brought in Josh Donaldson, Isiah Kiner-Falefa and Marwin Gonzalez, and made zero helpful additions to the pitching staff.

Re-signing Rizzo ended up being Cashman's best move. In hindsight, that couldn't be more underwhelming because of how badly the first baseman has struggled ever since the end of May when he collided with Fernando Tatis Jr. and subsequently suffered "cognitive impairment."

Even so, Rizzo, for as much as Yankees fans enjoy him, was far from the best player available (even at his position). That same offseason, the Yankees passed on Marcus Semien, Corey Seager, Kyle Schwarber, Joc Pederson, and perhaps most indefensibly, Freddie Freeman.

The Yankees badly needed an All-Star-caliber left-handed bat to sandwich into their unbalanced lineup. Rizzo, who was obviously an above-average option, had been underperforming since the start of the 2020 season, likely a signal that his better days were behind him.

Freeman? He was getting better with age. 2020 NL MVP. 2021 World Series champion. And just a year older than Rizzo.

Why was passing on Freeman, if he had considered New York, deemed indefensible? Mainly because of the report that surfaced about the Yankees' reservations about signing the seven-time All-Star.

Per Brendan Kuty of NJ.com at the time:

"But [Brian] Cashman told [Freeman's agent Casey] Close that he just didn’t see the budgetary space developing for the Yankees. With big money already committed to Gerrit Cole and Giancarlo Stanton, and with Aaron Judge’s free agency looming, the Yankees were not comfortable committing to another nine-figure contract."

Brendan Kuty, NJ.com

Ah, yes, that famous budget that has kept them from finding a left fielder for, what, three seasons now? Freeman had a limited market and was spurned by the team that drafted him when the Braves traded for Matt Olson (another massive Yankees miss). The Dodgers swooped in and signed Freeman to the same contract Carlos Rodón signed this offseason (six years, $162 million).

Freeman is now challenging Ronald Acuña for the NL MVP after finishing fourth in last year's race. In 2022, he led the NL in runs scored, hits, doubles and on-base percentage. He played in 159 games. He's making $27 million per season through 2027.

Meanwhile, the Yankees did another one of their pseudo impact moves that featured some sort of a discount coupon. They've invested over $60 million in Rizzo since the second half of 2021, which has gifted them a weak .235/.334/.433 stat line and career-high strikeout percentages.

Their logic was to avoid a longer-term contract for a better, aging player in favor of a short-term contract for a worse, aging player. The same offseason, they inherited $50 million of Josh Donaldson's money. The year after giving DJ LeMahieu $90 million.

The Yankees are always drawing the line somewhere, and it's always in the wrong places.